DE2155658A1 - Verfahren zum Nachweis und zur Bestimmung einer Komponente der Reaktion zwischen einer niedermolekularen Verbindung und einem Protein - Google Patents
Verfahren zum Nachweis und zur Bestimmung einer Komponente der Reaktion zwischen einer niedermolekularen Verbindung und einem ProteinInfo
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- DE2155658A1 DE2155658A1 DE19712155658 DE2155658A DE2155658A1 DE 2155658 A1 DE2155658 A1 DE 2155658A1 DE 19712155658 DE19712155658 DE 19712155658 DE 2155658 A DE2155658 A DE 2155658A DE 2155658 A1 DE2155658 A1 DE 2155658A1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/964—Chemistry: molecular biology and microbiology including enzyme-ligand conjugate production, e.g. reducing rate of nonproductive linkage
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/807—Apparatus included in process claim, e.g. physical support structures
- Y10S436/808—Automated or kit
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/815—Test for named compound or class of compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/815—Test for named compound or class of compounds
- Y10S436/817—Steroids or hormones
Description
betreffend
der Reaktion zwischen einer niedermolekularen Verbindung
und einem Protein
Zum Nachweis und zur Bestimmung niedermolekularer Substanzen, die in geringen Konzentrationen vorliegen,
wie Steroidhermonen in Körperflüssigkeiten, wurden Verfahren entwickelt, bei denen Proteine verwendet werden, die
fähig sind, die nachzuweisende Substanz spezifisch zu binden. Diese Verfahren beruhen auf der Konkurrenz zwischen
der nachzuweisenden Substanz in der Probe und einer bekannten Menge der gleichen Substanz, die radioaktiv markiert ist,
mit einer begrenzten Menge des spezifischen bindenden Proteins, Durch die unbekannte Menge der bindungsfähigen Substanz wird
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bestimmt * welcher Anteil der radioaktiv markierten Substanz
an das spezifische bindende Protein gebunden wird.
Es ist auch möglich, mit Hilfe dieser Verfahren, eine
unbekannte Menge eines spezifischen bindenden Proteins durch Umsetzung einer Probe, die eine unbekannte Menge des spezifischen
bindenden Proteins enthält, mit einer bestimmten Menge einer bindungsfähigen radioaktiv markierten Substanz zu bestimmen.
In der Literatur ist es üblich, diese Bestimmungsverfahren
je nach der Art des verv/endeten spezifischen bindenden
Proteins zu unterschieden, obwohl das grundlegende Prinzip all dieser Bestimmungen das gleiche ist. So wird z.B. von
"konkurrierenden Protein-Bindungsversuehen" ("competitive
protein binding assays") gesprochen, wenn Rezeptor-oder Transportproteine
verwendet werden, die im Körper vorkommen und von "radioimmunologischen Bestimmungen", wenn Antisubstanzen
verwendet werden.
Pur beide Arten von Bestimmungen sind radioaktiv markierte
Substanzen erforderlich. Das Arbeiten mit diesen Substanzen
erfordert das Vorhandensein präziser Meßvorrichtungen, gut ausgerüstete Laboratorien und ein qualifiziertes Personal.
Diese hohen Anforderungen machen eine allgemeine Anwendung dieser Bestimmungsverfahren besonders in kleineren Laboratorien
unmöglich.
Es wurde nun ein Verfahren gefunden zum Nachweis und zur Bestimmung einer Komponente der Reaktion zwischen einer
niedermolekularen Verbindung und einem Protein, das spezifisch diese Verbindung binden kann, wobei die Bindungsaffinität derartiger
Komponenten zueinander ausgenutzt wird, das dadurch
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gekennzeichnet ist, daß die Bestimmung mit einer bestimmten Menge des Kupplungsproduktes aus der niedermolekularen
Komponente und einem Enzym und mit einer bestimmten Menge einer Komponente dieser Reaktion durchgeführt wird, die unlöslich
gemacht worden ist-und die Enzymaktivität der flüssigen oder festen Phase des entstehenden Reaktionsgemisches bestimmt wird, die ihrerseits ein Haß.ist für die Menge der zu
bestimmenden Reaktionskomponente.
Dieses Verfahren kann häufig angewandt werden zur Bestimmung
von Haptenen, die als eine spezielle Gruppe niedermolekularer Verbindungen angesehen werden können, sowie ihrer
Antisubstanzen. Diese Substanzen treten meist in geringen Konzentrationen auf. liach der Definition von K. Landsteiner sind
Haptene proteinfreie Substanzen, deren chemische Konfiguration so ist, daß sie nicht mit spezifischen Antikörpern reagieren
können, jedoch auch nicht so, daß sie zur Bildung von Anti~ körpern führen können. Um jedoch trotzdem Antikörper zu Kaptenen
bilden zu können, müssen die Haptene, bevor sie dem Testtier injiziert werden, an Polypeptide gekuppelt werden.
Bei der Bestimmung einer niedermolekularen Verbindung konkurrieren die zu bestimmende Substanz und deren Kupplungsprodukt mit einem Enzym um eine bestimmte Menge des unlöslichen
spezifisch bindenden Proteins. Je mehr der niedermolekularen Verbindung die Probe enthält, um so geringer ist die Chance,
für das Kopplungsprodukt aus dem löslichen Enzym und der Verbindung, sich mit dem unlöslichen spezifischen bindenden
Protein zu verbinden und um so mehr des Kopplungsproduktes bleibt in der flüssigen Phase zurück, in der^nzymaktivität
auf einfache Weise gemessen werden kann.
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Bei der Bestimmung eines spezifischen bindenden.Proteins
mit den gleichen Reagentien treten das zu bestimmende lösliche Protein und das unlösliche Protein in Konkurrenz, um
eine bestimmte Menge des Kopplungsproduktes der entsprechenden niedermolekularen Verbindung und des Enzyms. Wenn der
Gehalt an spezifischem bindenden Protein in der Probe höher ist, wird das unlösliche Protein weniger von dem Enzym-Kopplungsprodukt
binden und folglich bleibt mehr Enzym in der flüssigen Phase zurück.
Ein spezifisches bindendes Protein mit zwei oder mehr bindenden Stellen kann ebenfalls nach dem erfindungsgemäßen
Verfahren nachgewiesen und bestimmt werden, d.h. mit dem
Enzym-Kopplungsprodukt und der niedermolekularen Verbindung
in unlöslicher Form. Die flüssige Phase des Reaktionsgeaisches
kann dann das Kopplungsprodukt an das spezifische bindende Protein gebunden enthalten und in der festen Phase kann der
Komplex aus Enzym-Kopplungsprodukt und spezifischem bindenden Protein und der in Wasser unlöslichen niedermolekularen Verbindung
enthalten sein. Je mehr des zu bestimmenden Proteins in der Probe enthalten ist, um so mehr Enzymaktivität besitzt
die flüssige Phase.
Mit Hilfe einer Bestimmungskurve für ein bestimmtes System, bei dem der zunehmende Gehalt an der zu bestimmenden
Substanz gegen die gefundene Enzymaktivität,vorzugsweise in
der flüssigen Phase, aufgetragen-ist, kann die Menge der in
der Probe enthaltenen zu bestimmenden Substanz für den gefundenen Wert für die Enzymaktivität abgelesen werden.
Das wichtigste Reagens für dieses"Bestimmungsverfahren
ist das Kopplungsprodukt aus der niedermolekularen Substanz und einem Enzym, im folgenden auch Enzym-Kopplungsprodukt
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genannt, das einerseits mit dem spezifischen bindenden Protein über die niedermolekulare Komponente reagieren kann und
andererseits Enzymaktivität besitzt. Dieses Reagens wird nach einem für ähnliche Produkte beschriebenen Verfahren hergestellt.
Das zweite Reagens, die unlösliche Komponente in dem Reaktionssystem dient zur Erleichterung der Trennung der verschiedenen
enzymhaltigen Fraktionen des Reaktionsgemisches. Die Zugabe dieses Reagenses führt zur Bildung einer festen.
Phase neben einer flüssigen Phase. Die angegebenen Bestimmungen können im Prinzip auch ohne unlösliche Komponente in dem Reaktionssystem
durchgeführt werden. In diesem Falle müssen die verschiedenen Fraktionen mit Enzymaktivität durch z.B. chromatographische
oder elektrophoretische Verfahren oder Gelfiltration getrennt werden. Aus praktischen Gründen ist jedoch, eine
derartige Bestimmung weniger günstig.
Die Enzymaktivität einer Fraktion des Reaktionsgemisches wird gezeigt oder gemessen, indem diese Fraktion mit einem
Substrat und anderen Substanzen zur Durchführung einer Enzymreaktion
inkubiert wird. Vorzugsweise wird eine Reaktion angewandt, bei der eine gefärbte Verbindung gebildet oder entfernt
wird, deren Absorption auch leicht quantitativ gemessen werden ka nn.
niedermolekulare Substanzen, die nach dem neuen Verfahren
nachgewiesen werden können und ein Molekulargewicht bis zu ungefähr 1 500 besitzen, sind zeB. Steroide, Vitamin B^2>
Folinsäure, Thyroxin und Trijodothyronin, releasing factors,
Histamin, Serotonin und andere biogene Amine, Digoxin, Digitoxin, Prostaglandine, Adrenalin, Nor-Adrenalin, pflanzliche
Hormone, wie Auxin, Kinetin, Giberellinsäure und Antibiotika,
wie Penicillin.
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Das Verfahren zum Nachweis spezifischer bindender Proteine für niedermolekulare Substanzen kann angewandt
werden, z.B. zur Bestimmung von Antigenen gegen Penicillin oder zur Bestimmung des Intrinsik-Paktors.
Die Herstellung von Kopplungsprodukten von Enzymen und niedermolekularen Substanzen kann auf verschiedene Weise
durchgeführt werden. Einige niedermolekulare Substanzen können schon Gruppen besitzen, die mit reaktionsfähigen
Gruppen an der Oberfläche des Enzyms vernetzt werden können, während andere Substanzen erst derartige Gruppen durch
chemische Reaktionen erhalten müssen. Es ist selbstverständlich, daß die ursprünglichen Bindungseigenschaften der niedermolekularen
Verbindung und die Aktivität des Enzyms während dieses Verfahrens nicht wesentlich geändert werden können.
Die Gruppen des Enzyms, die besonders geeignet sind für Kopplungsreaktionen sind Amino- und Carboxylgruppen. Wenn
die modifizierte oder nicht-modifizierte niedermolekulare Substanz ebenfalls derartige Gruppen besitzt, kann die Kopplung
z.B. durch Reaktionen, wie sie aus der Peptidsynthese
bekannt sind, durchgeführt werden. Darüberhinaus können solche Substanzen, wie Glutaraldehyd, Difluordinitrodiphenylsulfon,
Toluoldiisocyanat, Di- und Trichlor-s-triazin für
Kopplungsreaktion verwendet werden.
Spezielle Beispiele für die Kopplung von Haptenen mit1
Proteinen sind z.B. in Methods in Immunology and Immunochemistry, Band 1, beschrieben. Die dort beschriebenen Verfahren
werden angewandt zur Herstellung von Kopplungsprodukten
zur Immunisierung, sie können jedoch auch zur Herstellung von Kopplungsprodukten der niedermolekularen Substanz und eines
Enzyms angewandt werden, die für das erfindungsgemä3e Verfahren
wichtig sind.
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Die Wahl des Enzyms, das eine Komponente für das Kopplungssystem (niedermolekulare Substanz und Enzym) is
hängt ab von Eigenschaften wie der spezifischen Aktivität
(eine hohe Umwandlungsrate vergrößert die Empfindlichkeit des Testsystems) und der Einfachheit der Bestimmung des
Enzyms. Die Bestimmung eines Enzyms, das eine Umwandlung katalysiert, bei der gefärbte Produkte entstehen oder verschwinden,
ist einfach. Derartige colorimetrische Bestimmungen können auf einfache Weise automatisiert werden.
Erfindungsgemä3 ist es auch möglich, Enzyme zu verwenden,
die Umwandlungen katalysieren, bei denen Komponenten auftreten oder verschwinden, die spektrophotometrisch oder
fluorimetrisch bestimmt werden können. Diese Bestimmungen können ebenfalls automatisiert werden.
Für die Herstellung der Kopplungsprodukte werden Enzyme, wie Katalase, Peroxidase, ß-Glukuronidase, B-D-Glukosidase,
ß-D-Galactosidase, Urease, Glukose-oxidase und Galactoseoxidase bevorzugt, besonders die Gruppe der Oxido-reduktasen.
Das unlösliche spezifische bindende Protein oder die unlösliche niedermolekulare Verbindung, die bei der erfind
ungsgemäßen Bestimmung verwendet werden können, können auf bekannte Weise, z.B. durch Vernetzung mit Chlor-ämeisensäure-äthylester,
durch kovalente Bindung mit unlöslichen Trägern, wie Agarose, Vernetzung mit Dextran oder Filterpapier
oder durch physikalische Kopplung an unlösliche Träger, wie Kunststoffe,hergestellt werden.
Die Form, in der die Reagentien verwendet werden können,
ist vielfältig. Die Komponente des Reaktionssystems, die mit einem Enzym gekoppelt ist, kann gefriergetrocknet oder in
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einem Puffer gelöst sein. Darüberhinaus kann ein fester Träger, z.B. ein Papierstreifen, der mit dem Kopplungsprodukt imprägniert ist, verwendet v/erden.
Die unlösliche Komponente kann in Form von Teilchen verschiedener
Form, wie Körner, Kugeln und Stäbchen oder in Form eines Streifens des einen oder anderen Trägermaterials gebracht
werden.
Zur Durchführung des erfindungsgemäßen Verfahrens wird vorzugsweise eineTestpacK/V'erwendet, die hauptsächlich besteht
aus:
a) einer bestimmten Menge des Kopplungsproduktes aus einer
niedermolekularen Verbindung und einem Enzym;
b) einer entsprechenden Menge einer der Komponenten des Reaktionssystems in unlöslicher Form;
c) einem Substrat zur Bestimmung der Aktivität des verwendeten Enzyms.
Wenn erforderlich, kann die Testpackrauch die notwendigen
Hilfsmittel zur Herstellung einer Verdünnungsreihe der zu untersuchenden Probe für eine quantitative Bestimmung, wie
Reagenzgläaser, Pipetten und Kolben mit Verdünnungsmittel, enthalten. Zur Bestimmung eines Haptens enthält die Testpackung
mindestens
a) eine bestimmte Menge des Kopplungsproduktes dieses Haptens
mit einem Enzym;
b) eine entsprechende Menge einer Komponente des Reaktionssystems in unlöslicher Form, Haptenantikcrper;
c) ein Substrat zur Bestimmung der Enzymaktivität.
Die Erfindung wird durch die folgenden Beispiele näher erläutert.
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Beispiel 1
Bestimmung von Testosteron
Bestimmung von Testosteron
100 mg Testosteron-3-(0-earboxymethyl)-oxim und 0,143 ml
Tri-n-butylamin wurden in 5 ml Dioxan gelöst. Die Lösung wurde
auf 20G abgekühlt und dann wurden 0,03 ml Isobutylchlorcarbonat
zugegeben. Nach 30 min wurde die Lösung zu 100 mg HRP (Meerrettichperoxidase)
in einem Gemisch von 9 ml Wasser und 6 ml Dioxan zugegeben und mit 0,1 η NaOH auf einen pH-Wert von 9
eingestellt. Diese Lösung wurde 4 h bei 2°C gerührt und über
Nacht dialysiert. Der Niederschlag, der nach Einstellung des Dialysats auf einen pH-Wert von 4,6 erhalten worden war, wurde,
nachdem er über Nacht stehengelassen worden war, zentrifugiert, in 10 ml Wasser suspendiert und mit Hilfe von Natronlauge
gelöst. Das Material wurde dreimal mit 15 ml Aceton bei einem pH-Wert von 4,5 ausgefällt, in 15 ml Wasser, das mit Natriumhydroxid-Lösung
auf einen pH-Wert von 7,8 eingestellt war, gelöst, dialysiert und schließlich lyophilisiert.
Dieses Kopplungsprodukt wurde auf die gleiche Weise wie das Testosteron-3-HRP hergestellt, wobei jedoch als Ausgangsmaterial
50 mg Testosteron-3-(0-carboxymethyl)-oxim und 150 mg BSA (Rinderserumalbumin) verwendet wurden.
5 Kaninchen wurden intramuskulär zunehmende Dosen von Testosteron-3-BSA in vollständigem Freund'sehen Adjuvans(O,5,
1 und 2 mg) in Intervallen von 3 Wochen injiziert. Zwei Wochen
nach der letzten Injektion wurden den Tieren intravenös 2 mg
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Antigen in physiologischer Kochsalzlösung injiziert. Eine
Woche danach wurde den Tieren Blut abgenommen. Die gegen BSA gebildeten Antikörper wurden entfernt, indem das Serum anteilweise
mit BSA-m-aminobenzyloxymethylcellulose, die nach dem
Verfahren von Gurvich. (siehe D) hergestellt worden war, behandelt
wurde. .
Diese Substanz wurde entsprechend dem von Gurvich in
Biokhimiya 26, 934 (1961) beschriebenen Verfahren hergestellt.
1. Herstellung von "Aminocellulose":
50 g Whatman Cellulose, die mehrfach gewaschen und dekantiert worden war, wurden in 100 ml einer 0,7-prozentigen Natriumacetatlösung
suspendiert, die 2 g N(m-liitrobenzoxy)-methylpyridin
enthielt. Das Gemisch wurde bei 60 bis 800G getrocknet
und 40 min auf 125°C erhitzt. Das entstehende Produkt wurde gründlich mit destilliertem Wasser gewaschen,
bei 80'0C getrocknet, mit Benzol gewaschen und erneut getrocknet.
50 g des getrockneten Produktes wurden durch Suspension in 300 ml einer 15-prozentigen NapSpO.-lösung reduziert
und 30 min bei 50 bis 600C gerührt. Das Produkt wurde filtriert und nacheinander mit destilliertem Wasser,
30-prozentiger Essigsäure und wieder mit destilliertem Wasser gewaschen.
2. Behandlung mit ammoniakalischer Kupferlösung:
40 tal 10-prozentiger Schwefelsäure, 20 ml" 50-prozentiger
Salpetersäure und 140 ml destilliertes Wasser wurden unter Rühren auf 900C erhitzt. Anschließend wurden 5,9 g CuO
in kleinen Anteilen zugegeben. Die Lösung wurde 2 h zum Sieden erhitzt und mit destilliertem V/asser auf 500 ml aufgefüllt.
80 ml dieser Lösung wurden in ein Eisbad gegeben
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und unter Rühren zu 160 ml kalter 4 η HaOH zugegeben.
Fach 30-minütigem Rühren wurde der Niederschlag zweimal
mit destilliertem Wasser gewaschen und in 80 ml 25-prozentigem
Ammoniak gelöst. Zu dieser lösung wurde, nach und nach 1 g "Aminocellulose" zugegeben. Das Gemisch wurde
1.1/2 h gerührt und anschließend wurden 40 ml siedendes Wasser zugegeben und die Lösung schnell auf 00G abgekühlt.
Die Lösung wurde mit 10-prozentiger Schwefelsäure
neutralisiert, worauf die Aminocellulose ausflockte. Sie wurde mit kaltem destillierten Wasser gewaschen.
Herstellung von ^-Globulin:
Zu Kaninchen Antitestosteronserum wurden 180 mg NapSO,
pro ml" Serum zugegeben. Das Gemisch wurde 1 h bei Raumtemperatur gerührt und der entstehende Niederschlag zentrifugiert,
zweimal mit einer 18-prozentigen Na2SO,-Lösung
gewaschen und in so viel 0,05 m Natriumborat mit einem pH-Wert von 8,6 aufgenommen, daß die Proteinkonzentration
ungefähr 10 mg/ml betrug.
Bindung des ^Globulins an Aminocellulose: 350 mg "Aminocellulose" wurden in 50 ml destilliertem
Wasser suspendiert. Die Suspension wurde auf 00C abgekühlt.
10 ml 36-prozentige Salzsäure wurden zugegeben und anschließend 10 ml 10-prozentige MaHOp-Lösung zugetropft.
Die Suspension wurde zentrifugiert, mit kaltem destillierten V/asser und anschließend mit 0,05 m Natriumborat
mit einem pH-Wert von 8,6 gewaschen. Die Cellulose wurde in 43 ml 0,05 m Natriumborat mit einem pH-Wert von 8,6 suspendiert.
Zu dieser Suspension wurden 7 ml der wie oben hergestellten jf-Globulinlösung zugegeben. Das Gemisch wurde
26 h bei 4°C gerührt, zentrifugiert und mit 0,02 m Phosphatpuffer
mit einem pH-Wert von 6,0 gewaschen. Von dein Anti-
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serum.jedes der 5 immunisierten Kaninchen wurde eine
Cellulose suspension hergestellt (A bis E).
E) Bestimmung von Testosteron mit Hilfe von Testosteron-3-HRP und Antitestosteroncellulose
Das folgende System wurde aufgebaut:
Das folgende System wurde aufgebaut:
I) Immunreaktion
0,5 ml einer Probe, enthaltend Testosteron, 0,2 ml
Testosteron-3-HRP (100 mg/ml) und 0,3 ml einer Antitestosteroncellulose-Suspension
wurden 2 h bei Raumtemperatur rotiert und dann 5 min mit 1 000 g zentrifugiert.
Die Immunreaktion fand in 0,02 m Phosphatpuffer bei einem pH-Wert von 6,0, enthaltend 2 "$>
Schafserum, statt,
II) Enzymreaktion
0,5 ml der überstehenden Flüssigkeit wurden bei Raumtemperatur mit 1,5 ml Substrat 30 min inkubiert. Die
Extinktion wurde bei 460 nm gemessen.
Das Enzymsubstrat enthielt 10 /ul, 30-prozentiges
Wasserstoffperoxid und 20 mg 5-Aminosalicyls-ture in
150 ml 0,02 m Phosphatpuffer mit einem pH-Wert von 6,2.
Die Fig. 1 zeigt Meßwerte, bei denen Testosteron-3-HRP
an die Antitestosteroneellulose-Zubereitungen gebunden worden ist. In diesem Falle wurde nur Puffer als
Probe in dem Testsystem zugegeben. Wenn Cellulose anstelle von Antitestosteroncellulose zugegeben wird,
bleiben mehr als 95 i° der Enz/maktivität in der überstehenden
Flüssigkeit enthalten, -^i e Zubereitungen B, D
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und E zeigten, da;3 fast kein Testosteron-3-HRP gebunden
worden war, jedoch "bei' den Zubereitungen A und C.
Pig. 2 zeigt die Ergebnisse der Inkubation einer Testosteronverdünnungsreihe mit Testosteron-3-HRP.
bei vier verschiedenen Konzentrationen von Antitestosteroneellulose C.
1 mg/ml (I), 2 mg/ml (II), 4 mg/ml (III) und 16 mg/ml
(IV). Es ist offensichtlich, da;d mit diesem System eine
Menge von ungefähr 10 ng Testosteron gezeigt werden kann.
A) Östradiol-17-succinyl-HRP wurde hergestellt durch die
in Beispiel 1 A) beschriebene gemischte Anhydrid-Methode, wobei 50 mg Östradiol-17-hemisuccinat und 50 mg HRP als
Ausgangsraaterialien verwendet wurden.
B) Östradiol-17-succinyl-BSA wurde nach der in Beispiel 1 A)
beschriebenen gemischten Anhydrid-Methode hergestellt, wobei 100 mg Östradiol-17-hemisuccinat und 150 mg BSA als
Ausgangsmaterialien verwendet wurden.
C) Zur Herstellung der Antikörper gegen Östradiol-17-succinyl-BSA
wurden 5 Kaninchen nach dem in Beispiel 1 C) beschriebenen Schema immunisiert. Die Sera wurden mit BSA-m-Aminobenzyloxymethylcellulose
absorbiert.
D) Antiöstradiolcellulose wurde auf die in Beispiel 1 D)
für Antitestosteroncellulose beschriebene Weise hergestellt.
Von jedem der immunisierten Kaninchen wurde■eine Cellulose-
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Zubereitung hergestellt, die mit 16 bis einschließlich 20 numeriert wurden.
E) Die Untersuchung wurde analog derjenigen für Testosteron in Beispiel 1 B) durchgeführt.
Die Pig. 3 und 4 zeigen einige Ergebnisse. Die Fig. 3 zeigt, daß drei verwendbare Antisera durch die Immunisierung
erhalten wurden, von denen 17 den höchsten Titel besitzt. Die Fig. 4 zeigt das Testsysteni,bei dem Antiöstradidcellulose
17 in einer Konzentration von 8 mg/ml verwendet wurde. Das System unterscheidet nicht zwischen
Östron und 17ß-Östradiol. 17a-Östradiolf besonders Östriol,
zeigen eine geringere Kreuzreaktion. Testosteron und Progesteron beeinflussen das System nur in sehr hohen
Konzentrationen.
Penicilloyl-Katalase
30 mg Benzy!penicillinsäure wurden in 5 ml 96-prozentigem
Äthanol gelöst und zu 200 mg Katalase in 45 ml 0,1 m Phosphatpuffer mit einem pH-Wert von 7,5 zugetropft. Die Reaktion
wurde 2 h fortgesetzt, wobei der pH-¥ert mit 0,5 n NaOH zwischen
7,2 und 8,2 gehalten wurde. Das Reaktionsgemisch wurde gegen 6 χ 3 1 0,02 m Phosphatpuffer mit einem pH-Wert von 7,0
dialysiert.
Auf die gleiche Weise wurden 250 mg BenzyIpenicillinsaure
an 5 g m-Aminobenzyloxymethylcellulose, die nach dem Verfahren
von Gurvich (Biokhimiya 26, 934 (1961)) hergestellt worden war, gekoppelt. Das Kopplungsprodukt wurde jedoch nicht dialysiert;,
sondern auf einem Glasfilter gewaschen.
. - 15 -
209821/0660
- 15 - 1A-40 490
Eine Überempfindlichkeit von Menschen gegenüber Penicillin konnte auf folgende Weise gezeigt werden:
0,2 ml einer Probe von nicht-hämolysiertem Serum wurden
mit 0,5 ml einer Lösung von Penicilloyl-Katalase (1:800) vermischt. Nach 30 min wurden 10 mg Penicilloyl-m-aminobenzyloxymethylcellulose
zugegeben. Das Gemisch wurde 50 min rotiert und anschließend die Enzymaktivität in der überstehenden
Flüssigkeit bestimmt, indem 0,02 ml dieser Flüssigkeit zu 2,8 ml 0,05 m Phosphatpuffer mit einem pH-Wert von 6,8
zugegeben wurden, der 1,2 /al 30-prozentiges K2O2 enthielt
und anschließend die Abnahme der Extinktion bei 240 nm
wurde
gemessen/iim Serum von Patienten, die gegenüber Penicillin überempfindlich waren, wurde eine geringere Enzymaktivität in der Flüssigkeit gefunden als bei Kaninchenserum. Die V/erte für Menschen, die nicht überempfindlich waren, wichen nicht wesentlich von denjenigen mit Kaninchenserum ab.
gemessen/iim Serum von Patienten, die gegenüber Penicillin überempfindlich waren, wurde eine geringere Enzymaktivität in der Flüssigkeit gefunden als bei Kaninchenserum. Die V/erte für Menschen, die nicht überempfindlich waren, wichen nicht wesentlich von denjenigen mit Kaninchenserum ab.
A) Herstellung von Folatglukoseoxidase
200 mg Glukoseoxidase (140 IU/mg) wurden in 10 mg
PBS (mit Phosphat gepufferte Salzlösung, eine phosphathaltige physiologische Kochsalzlösung) mit einem pH-Wert
von 7,0 gelöst. 30 mg 1-Cyclohexyl-3-(2-morpholinoäthyl)-carbodiimid
(MCDI) wurden zugegeben und anschließend 24 mg Folinsäure. Die Reaktion dauerte 2h und anschließend
wurde eine sorgfältige Dialyse gegen PBS mit einem pH-Wert von 7,0 durchgeführt.
B) Herstellung von Folat-MBSA (methyliertes Rinderserumalbumin}
Folat-MBSA wurde hergestellt nach dem von Ricker und
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Stollar beschriebenen Verfahren (Biochemistry 6, 2001 (1967))· 25 mg MGDI wurden zu 50 mg BSA in 50 ml Wasser
zugegeben und anschließend 20 mg Polinsäure. 2 h später
hatte sich ein gelber Niederschlag gebildet. Schließlich wurde das ganze Reaktionsgemisch eine beträchtliche Zeit
gegen physiologische Kochsalzlösung dialysiert.
C) Herstellung von Antiseruin gegen Folat-MBSA
Am. Tage 0, 21 und 42 wurden jeweils 4 Kaninchen
intramuskulär 2 mg Folat-MBSA in vollständigem Freund'sehen
Adjuvans und am Tage 35 intravenös 2 mg Folat-MBSA
in physiologischer Kochsalzlösung injiziert. Am Tage 49 wurde den Tieren Blut abgenommen.
D) Antifolatcellulose wurde entsprechend dem in Beispiel 1 D)
beschriebenen Verfahren hergestellt.
E) Bestimmung von Polinsäure
100 /Ul der zu untersuchenden Probe und 700 /ul einer
Antifolatcellulose-Suspension wurden 3 h rotiert. 200 /ul
Polatglukoseoxidase (1:1500) wurden zugegeben. Das Gemisch wurde nochmals 3 h rotiert und zentrifugiert.und anschließend
die Enzymaktivität in der überstehenden Flüssigkeit bestimmt. Diese Bestimmung v/urde durchgeführt durch Vermischen
von 0,5 ml der überstehenden Flüssigkeit mit einer lösung von 50 mg Glukose, 10 /Ug HR? und 1 mg 5-Aminosalicylsäure
in 2,5 ml 0,05 η Phosphatpuffer mit einem pH-Wert von 6,0 und Messung der Extinktion nach 30 min bei
460 nm.
Pig. 5 zeigt den Prozentsatz des gebundenen Enzyms gegen die Konzentration der Antifolatcellulose.
- 17 20982 1/0660
- 17 - 1A-40 490
Pig. 6 zeigt die Emfindliehkeit des Testsystems in einer Antifolatcellulose-Konzentration von 2 mg/ml
und die Wirkung von Glycin, Asparagin, Alanin,und Glutamin säure.
A) Herstellung von Digoxin-HRP ,
abs.
Zu 22mg Digoxin,in 1 ml/Äthanol suspendiert ,wurde
unter Rühren 1 ml 0,1 m Natriummetaperjodat zugetropft.
Nach 25 min wurden 0,3 ml 0,1 m Äthylenglykol zugegeben. 5 min später wurde dieses Gemisch unter Rühren zu einer
Lösung von 32 mg Meerrettichperoxidase (HRP) in 1 ml destilliertem Wasser zugetropft, das mit 5-prozentiger
K2CO,-Lösung auf einen pH-Wert von 9,5 eingestellt war.
Während der Reaktion wurde der pH-Wert durch Zugabe 5-prozentiger KpGO,-Lösung auf 9 bis 9,5 gehalten. Als
der pH-Wert stabil war, wurden 15 mg NaBH. in 1 ml destilliertem Wasser zugegeben. Nach 3 h wurde der pH-Wert mit
1 m Ameisensäure auf 6,5 eingestellt. 1 h später wurde 1 m lTH.OH zugegeben, bis ein pH-Wert von 8,5 erreicht war.
Das Gemisch wurde über Nacht gegen kaltes fließendes Wasser dialysiert. Schließlich wurde der pH-Wert mit 0,1 η Salzsäure
auf 4,5 eingestellt. Das Gemisch wurde 1 h bei Raumtemperatur und 4 h bei 40C stehengelassen, um einen
Niederschlag zu erhalten, der 1 h bei 1 000 g zentrifugiert wurde. Der niederschlag wurde in 5 ml 0,1 m NaHCO, gelöst,
gründlich dialysiert und gefriergetrocknet.
B) Herstellung von Digoxin-BSA
Digoxin-Rinderserumalbumin (BSA) wurde auf die
gleiche V/eise, wie sie oben für Digoxin-HRP angegeben ist,
- 18 209821/0660
- 18 - ' 1A-40 490
hergestellt, wobei jedoch von 436 mg Digoxin und 560 mg
BSA ausgegangen wurde und· die Mengen der anderen Reagenzen in gleichem Verhältnis erhöht wurden wie das Dioxin.
C) Herstellung von Antikörpern gegen
5 Kaninchen wurden 400, 800 bzw.1 600 /Ug Dioxin-BSA im Abstand von 14 Tagen injiziert. Das Immunogen wurde
mit vollständigem Freund •sehen Ad juvans vermischt und intramuskulär
verabreicht. 14 Tage nach der letzten Injektion wurde den Tieren intravenös 800 /ug Digoxin-BSA in physiologischer
Kochsalzlösung injiziert. 10 Tage später wurde
das
den Tieren/Blut entnommen. Das Serum wurde mit BSA-m-Aminbenzyloxymethylcellulose adsorbiert.
den Tieren/Blut entnommen. Das Serum wurde mit BSA-m-Aminbenzyloxymethylcellulose adsorbiert.
D) Herstellung von Antidigoxincellulose
Antidigoxincellulose wurde nach dem Gurvich-Verfahren,
wie unter 1 D) beschrieben, hergestellt.
B) Bestimmung von Digoxin
Eine Verdünnungsreihe wurde mit Digoxin in 0,1 m Phosphatpuffer mit einem pH-Wert von 7,5 hergestellt, enthaltend
0,9 i» NaCl, 0,5 # Tween-20 und 1,0 <$>
BSA. Die Verdünnungsreihe ging von 0,1 bis 100 ng/ml. 1 ml einer
Digoxin-Lösung wurde mit 0,1 ml Digoxin-HRP in einer
geeigneten Verdünnung νermiseht.und anschließend wurden
2 mg Antidigoxincellulose, die in 0,4 ml Puffer suspendiert war, zugegeben. Das Gemisch wurde 6 h. bei Raumtemperatur
rotiert und anschließend zentrifugiert.und die Enzymaktivität in der überstehenden flüssigkeit bestimmt.
Zugabe von 0,8 ng Digoxin führte zu einer meßbaren Zunahme der Enzymaktivität in der überstehenden Flüssigkeit.
Digoxin allein zeigte eine geringe Kreuzreaktion in dein
- 19 209821/0660
215565a
- 19 - 1A-40 490
System während Cholesterin,Cortisol, Östradiol, Testosteron
und Progesteron keine Kreuzreaktion in dem System zeigten,
Beispiel 6
A) Herstellung von Cortisol-21-galactose-oxidase
50 mg Cortisol-21-hemisuccinat und 100 mg Galactoseoxidase
wurden nach dem in Beispiel 1 A) "beschriebenen gemischten Anhydridverfahren hergestellt.
B) Herstellung von unlöslichem Transkortin
100 mg Transcortin, das durch Chromatographie mit
DEAE, Cellulose bzw. Hydroxylapatit gereinigt worden war,
wurden folgendermaßen mit Hilfe des CNBr-Verfahrens an
3 g Sepharose 4 B gekoppelt: 3g Sepharose 4 B-Suspension
wurden aktiviert durch Vermischen mit 4 ml einer 2,5-prozentigen (Gew./Vol.) CNBr-lösung in destilliertem
Wasser und anschließend wurde der pH-Wert mit 1 η NaOH auf 10 "bis 11 eingestellt und 6 min auf diesem Wert
gehalten. Me Sepharose wurde mit Eiswasser und 0,1 m NaHCO, gewaschen. Dann wurden 100 mg Trans cortin in 20 ml
0,1 m NaHCO, zugegeben und die Suspension 24 h bei 4°C
geschüttelt. Dannwurde nacheinander mit 0,5 m NaHCO,, 0,05 m Citratpuffer mit einem pH-Wert von 1,1 und 0,05 m
Phosphatpuffer mit einem pH-Wert von 6 gewaschen und die Sepharose in dem letzten Puffer gelassen, zu dem 0,1 $
Merthiolat zugegeben worden war.
C) Bestimmung von Cortisol
0,5 ml einer cortisolhaltigen Probe (Standard, Plasna oder Urin) wurden zweimal mit Methylenchlorid extrahiert
(2x3 ml). Die vereinigten Auszüge wurde zur Trockne einge-
- 20 209821/0660
- 20 - 1A-40 490
dampft. Der Rückstand würde in 0,5 ml physiologischer
Kochsalzlösung aufgenommen und mit 0,2 inl Cortisol-21-galäotose-oxidase
in einer geeigneten Konzentration und 0,3 ml Transcortih-Sepharose-Suspension (5 mg/ml) vermischt«
Das Gemisch wurde 15 min bei 4°C rotiert und zentrifugiert.
Anschließend würde die Enzymäktivität in der überstehenden
Flüssigkeit durch Zugabe von 0,5 mT dieser
Flüssigkeit zu 1,5 ml eines Substrats bestimmt« Das Substrat
bestand aus 100 mg D-Gaiactose, 20 mg 5-Aminosalicylsäure
und 10 /ug Peroxldase in Ί50 ml 0,02 m Phosphatpüffer
mit einem pH-Wert von 6,0. 30 min später wurde
die Extinktion bei 460 nm gemessen.
5 Jig/ml Cortisol in der Probe führten zu einer meßbaren
Zunahme der Enzymaktivität in der überstehenden Flüssigkeit. Corticosteron und Progesteron beeinflussen
das System nur, wenn größere Mengen zugegeben würde. Testosteron und Aldosteron besaßen kaum einen Einfluß.
Beispiel 7 *
Die zur Bestimmung von Cortisol, wie in Beispiel 6 beschrieben,
verwendeten Reagentien wurden ebenso zur Bestimmung von Transcortin verwendet.
Von einer Veraünnungsreine von Transcortin von 0 bis
280 ng/ml wurden 0,5 ml 15 min bei 4°C mit 0,2 ml Cortisol-•21-galactose-oxidase
in einer entsprechenden Verdünnung inkubiert. Zu dieser Verdünnungsreihe wurden 0,3 ml Transcortin-Sepharose
(15 mg/ml) zugegeben und aas Gemisch i5/bei 4°C
rotiert. Die Aktivität der überstehenden Flüssigkeit wurde, ■ wie in Beispiel 6 beschrieben, gemessen.
- 21 -
209821 /0660
- 21 - 11-40
Eine Probe, enthaltend 40 ng/ml Transcortin, zeigte
eine meßbare Zunahme der Enzymaktivität in der überstehenden Flüssigkeit, während sich bei Gegenwart von 320 ng/ml die
gesamte Enzymaktivität in der überstehenden Flüssigkeit fand. · . .
209821/0660
Claims (8)
- Patentansprüche/ 1. ) Verfahren zum Nachweis und zur Bestimmung einer Komponente der Reaktion zwischen einer niedermolekularen Verbindung und einem Protein, das diese Verbindung spezifisch binden kann unter Ausnutzung der für derartige Bestandteile bekannten Bindungsaktivität, dadurch gekennzeichnet, daß die Bestimmung mit einer bestimmten Menge des Kopplungsproduktes der niedermolekularen Verbindung und eines Enzyms und mit einer bestimmten Menge einer Komponente dieser Reaktion, die in unlösliche Form gebracht worden ist, durchgeführt wird und die Enzymaktivität, die ein Maß für die Menge der zu bestimmenden Reaktionskomponente ist, in der flüssigen oder festen Phase bestimmt wird,
- 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß ein Hapten oder dessen Antikörper mit einem Kopplungsprodukt aus diesem Hapten und einem Snzyra und einem in unlösliche Form gebrachten Bestandteil der Reaktion Hapten-Antikörper bestimmt wird.
- 3. Verfahren zur Herstellung des in Anspruch 1 und 2 erwähnten Kopplungsproduktes, dadurch gekennzeichnet, daß eine niedermolekulare Verbindung- 23 -209821/0660- 23 - iA-40oder ein Derivat dieser Verbindung mit einem Enzym in an sich bekannter Weise gekoppelt wird»
- 4. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß ein Haßten als niedermolekulare Substanz verwendet wird.
- 5. Verfahren nach Anspruch 4» dadurch gekennzeichnet, daß ein Vitamin oder Hormon als Hapten verwendet wird.
- 6. Verfahren nach Anspruch 3 bis 5» dadurch gekennzeichnet , daß eine Oxidoreduktase als Enzym verwendet wird.
- 7. Testpackung zur Durchführung des Verfahrens nach Anspruch 1, gekennzeichnet durch einen Gehalt ana) einer bestimmten Menge des Kopplungsproduktes der niedermolekularen Verbindung mit einem Enzyms;b) einer entsprechenden Menge eim:Komponenten des Reaktionssystems in unlöslicher Form;c) einem Substrat zur Bestimmung der Aktivität des verwendeten Enzyms.
- 8. Testpackung zur Durchführung .des Verfahrens nach Anspruch 2, gekennzeichnet durch einen Gehalt anä) einer bestimmten Menge des Kopplungsproduktes, des Haptens und eines Enzyms;b) einer entsprechenden Menge einer der Komponenten des Reaktionssystems Hapten-Antikörper in unlöslicher Form; ·c) einem Substrat zur Bestimmung der Aktivität des verwendeten Enzyms. " .-209821/0660ι 5^ ·♦Leerseite
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL707016396A NL154598B (nl) | 1970-11-10 | 1970-11-10 | Werkwijze voor het aantonen en bepalen van laagmoleculire verbindingen en van eiwitten die deze verbindingen specifiek kunnen binden, alsmede testverpakking. |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2155658A1 true DE2155658A1 (de) | 1972-05-18 |
DE2155658B2 DE2155658B2 (de) | 1976-08-05 |
DE2155658C3 DE2155658C3 (de) | 1978-09-14 |
Family
ID=19811504
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2155658A Expired DE2155658C3 (de) | 1970-11-10 | 1971-11-09 | Verfahren zum Nachweis und zur Bestimmung von einem Hapten oder dessen Antikörper |
Country Status (16)
Country | Link |
---|---|
US (1) | US3850752A (de) |
AU (1) | AU468060B2 (de) |
BE (1) | BE775187A (de) |
BR (1) | BR7107459D0 (de) |
CA (1) | CA967464A (de) |
CH (1) | CH617774A5 (de) |
DE (1) | DE2155658C3 (de) |
DK (1) | DK140268B (de) |
ES (1) | ES396741A1 (de) |
FI (1) | FI54033C (de) |
FR (1) | FR2113733A5 (de) |
GB (1) | GB1348935A (de) |
IT (1) | IT986829B (de) |
NL (1) | NL154598B (de) |
SE (1) | SE451162B (de) |
ZA (1) | ZA717192B (de) |
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Family Cites Families (2)
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---|---|---|---|---|
US3615222A (en) * | 1968-09-04 | 1971-10-26 | New England Nuclear Corp | Method and apparatus for measuring the amount of a component in a biological fluid |
US3654090A (en) * | 1968-09-24 | 1972-04-04 | Organon | Method for the determination of antigens and antibodies |
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1970
- 1970-11-10 NL NL707016396A patent/NL154598B/xx not_active IP Right Cessation
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1971
- 1971-10-27 ZA ZA717192A patent/ZA717192B/xx unknown
- 1971-10-28 AU AU35082/71A patent/AU468060B2/en not_active Expired
- 1971-10-29 US US00193702A patent/US3850752A/en not_active Expired - Lifetime
- 1971-11-04 FI FI3155/71A patent/FI54033C/fi active
- 1971-11-06 ES ES396741A patent/ES396741A1/es not_active Expired
- 1971-11-08 CH CH1621671A patent/CH617774A5/de not_active IP Right Cessation
- 1971-11-08 DK DK546271AA patent/DK140268B/da not_active IP Right Cessation
- 1971-11-09 BR BR7459/71A patent/BR7107459D0/pt unknown
- 1971-11-09 CA CA127,217A patent/CA967464A/en not_active Expired
- 1971-11-09 SE SE7114278A patent/SE451162B/xx unknown
- 1971-11-09 GB GB5196171A patent/GB1348935A/en not_active Expired
- 1971-11-09 DE DE2155658A patent/DE2155658C3/de not_active Expired
- 1971-11-09 IT IT53970/71A patent/IT986829B/it active
- 1971-11-10 FR FR7140259A patent/FR2113733A5/fr not_active Expired
- 1971-11-10 BE BE775187A patent/BE775187A/nl not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS4943479A (de) * | 1972-07-05 | 1974-04-24 |
Also Published As
Publication number | Publication date |
---|---|
NL154598B (nl) | 1977-09-15 |
FI54033B (fi) | 1978-05-31 |
ZA717192B (en) | 1972-08-30 |
FI54033C (fi) | 1978-09-11 |
SE451162B (sv) | 1987-09-07 |
DE2155658C3 (de) | 1978-09-14 |
BE775187A (nl) | 1972-03-01 |
BR7107459D0 (pt) | 1973-06-21 |
IT986829B (it) | 1975-01-30 |
ES396741A1 (es) | 1975-05-16 |
DK140268C (de) | 1979-12-10 |
NL7016396A (de) | 1972-05-15 |
DK140268B (da) | 1979-07-16 |
GB1348935A (en) | 1974-03-27 |
DE2155658B2 (de) | 1976-08-05 |
AU3508271A (en) | 1973-05-03 |
AU468060B2 (en) | 1975-12-18 |
US3850752A (en) | 1974-11-26 |
CA967464A (en) | 1975-05-13 |
CH617774A5 (de) | 1980-06-13 |
FR2113733A5 (de) | 1972-06-23 |
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