O-(Acridinium)hydroxylamine (AHA): A reagent for the preparation of chemiluminescent acridinium oxime (AO)-steroid conjugates

Steroids

Volumn 65, Issue 7, 2000, Pages 387-394

  Adamczyk, Maciej ^a   Grote, Jonathan ^a   Mattingly, Phillip G ^a   Pan, You ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Acridinium steroid conjugates; O (Acridinium)hydroxylamine; Tracers

Indexed keywords

ACRIDINE DERIVATIVE; DIGITOXIN; ESTRADIOL; ESTRADIOL DERIVATIVE; ESTRONE; ESTRONE DERIVATIVE; HYDROCORTISONE; NORETHISTERONE; NORETHISTERONE DERIVATIVE; PROGESTERONE; PROGESTERONE DERIVATIVE; REAGENT; STEROID; TESTOSTERONE;

ARTICLE; CHEMOLUMINESCENCE; DRUG CONJUGATION; DRUG LABELING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; REACTION ANALYSIS;

ACRIDINES; CHEMILUMINESCENT MEASUREMENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OXIMES; STEROIDS;

EID: 0033919351     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(00)00095-7     Document Type: Article

References (37)

1. Wild D. The immunoassay handbook. 1994;Stockton Press, New York.
2. Satoh D., Aoyama K. Studies on digitalis glycosides. XXXI. Stepwise degradation of polydigitoixosides of cardenolides. Chem Pharm Bull. 18:(1):1970;94-99.
3. Ide H., Akamatsu K., Kimura Y., et al. Synthesis and damage specificity of a novel probe for the detection of abasic sites in DNA. Biochemistry. 32:(32):1993;8276-8283.
4. Kubo K., Ide H., Wallace S.S., Kow Y.W. A novel, sensitive, and specific assay for abasic sites, the most commonly produced DNA lesion. Biochemistry. 31:(14):1992;3703-3708.
5. Adamczyk M., Mattingly P.G., Moore J.A. O-(Fluoresceinylmethyl)hydroxylamine (OFMHA) a fluorescent reagent for detection of damaged nucleic acids . Bioorg Med Chem Lett. 8:(24):1998;3599-3602.
6. Adamczyk M., Chen Y.-Y., Grote J., Mattingly P.G. O-(Fluoresceinylmethyl)hydroxylamine (OFMHA) a reagent for the preparation of fluorescent O-(fluoresceinylmethyl)oxime (FMO)-steroid conjugates . Steroids. 64:1999;283-290.
7. Makrigiorgos G.M., Chakrabarti S., Mahmood A. Fluorescent labeling of abasic sites a novel methodology to detect closely-spaced damage sites in DNA . Int J Radiat Biol. 74:(1):1998;99-109.
8. Boturyn D., Boudali A., Constant J.-F., Defrancq E., Lhomme J. Synthesis of fluorescent probes for the detection of abasic sites in DNA. Tetrahedron. 53:(15):1997;5485-5492.
9. Adamczyk M., Mattingly P.G., Moore J.A., Pan Y. Synthesis of a chemiluminescent acridinium hydroxylamine (AHA) for the direct detection of abasic sites in DNA. Org Lett. 1:(5):1999;779-781.
10. 10-(3-sulfopropyl)-N-sulfonylacridinium-9-carboxamides. Tetrahedron. 55:(36):1999;10899-10914.
11. Adamczyk M., Chen Y.-Y., Mattingly P.G., Pan Y. Neopentyl 3-triflyloxypropanesulfonate. A reactive sulfopropylation reagent for the preparation of chemiluminescent labels. J Org Chem. 63:(16):1998;5636-5639.
12. Akhavan-Tafti H., DeSilva R., Arghavani Z., et al. Characterization of acridancarboxylic acid-derivatives as chemiluminescent peroxidase substrates. J Org Chem. 63:(4):1998;930-937.
13. Kricka L.J. Chemiluminescence and bioluminescence. Anal Chem. 71:1999;305R-308R.
14. Mayer A., Neuenhofer S. Luminescent labels - more than just an alternative to radioisotopes? Angew Chem Int Eng Ed. 33:1994;1044-1072.
15. Jandreski M.A. Chemiluminescence technology in immunoassays. Lab Med. 29:(9):1998;555-560.
16. Barnard G., Brockelbank J.L., Kim J.B., Collins W.P. The use of isoluminol and acridinium labels in immunoassay. Kricka L. Analytical Applications of Bioluminescence and Chemiluminescence. Proceedings of the 3rd International Symposium. 1984;159-162 Academic Press, London.
17. De Boever J., Kohen F., Dhont M., Vanderkerckhove D., Van Maele G. Serum estradiol measurement by solid-phase chemiluminescence immunoassay and direct radioimmunoassay. Anal Chim Acta. 170:1985;117-123.
18. Abdel-Sayed W.S. Chemiluminescence and time resolved fluoro immunoassays of plasma estradiol and salivary progesterone. Alexandria J Pharm Sci. 3:(2):1989;131-134.
19. De Boever J., Kohen F., Bosmans E. Antibody binding efficiency of differently labeled steroid hormones. Anal Chim Acta. 275:(1-2):1993;81-87.
20. De Boever J., Ulrix W., Vandederckhove D. Chemiluminescence immunoassay for estriol in saliva. Anal Chim Acta. 205:(3):1988;215-222.
21. Klingler W., Wiegand G., Knuppen R. Chemiluminescent labels for steroid immunoassays. J Steroid Biochem. 27:(1-3):1987;41-45.
22. Klingler W., Haupt O., Von Postel G., Knuppen R. Immunoassay of unconjugated estriol in serum of pregnant women monitored by chemiluminescence. Steroids. 42:(2):1983;123-136.
23. Adamczyk M., Grote J. Efficient synthesis of 3-aminodigoxigenin and 3-aminodigitoxigenin probes. Bioorg Med Chem Lett. 9:(5):1999;771-774.
24. Adamczyk M., Johnson D.D., Reddy R.E. Synthesis of 6β-[(2′-aminoethyl)carboxamidomethyl]estradiol and preparation of estradiol probes. Bioconjugate Chem. 9:(3):1998;403-408.
25. Adamczyk M., Chen Y.-Y., Moore J.A., Mattingly P.G. Estradiol-mimetic probes. Preparation of 17α-(6-aminohexynyl)estradiol biotin, fluorescein and acridinium conjugates. Bioorg Med Chem Lett. 8:1998;1281-1284.
26. Sato H., Mochizuki H., Tomita Y., Kanamori T. Enhancement of the sensitivity of a chemiluminescent immunoassay for estradiol based on hapten heterology. Clin Biochem. 29:(6):1996;509-513.
27. Sato H., Mochizuki H., Tomita Y., Izako T., Sato N., Kanamori T. Competive chemiluminescent immunoassay for estradiol using an N-functionalized acridinium ester. J Biolumin Chemilumin. 11:1996;23-29.
28. Adamczyk M., Mattingly P.G., Reddy R.E. The synthesis of 6β-amino-estradiol and its biotin, acridinium, and fluorescein conjugates. Steroids. 63:(3):1998;130-134.
29. Richardson A.P., Kim J.B., Barnard G.J., Collins W.P., McCapra F. Chemiluminescence immunoassay of plasma progesterone, with progesterone-acridinium ester used as the labeled antigen. Clin Chem. 31:(10):1985;1664-1668.
30. Miller SA, Morton MS, Turkes A. Chemiluminescence immunoassay for progesterone in plasma incorporating acridinium ester labelled antigen. Ann Clin Biochem 1988;25 (Pt 1):27-34.
31. Janoski A.H., Shulman F.C., Wright G.E. Selective 3-(O-carboxymethyl)oxime formation in steroidal 3,20-diones for hapten immunospecificity. Steroids. 23:(1):1974;49-64.
32. Mattingly P.G. Chemiluminescent 10-methylacridinum-9-(N-sulfonylcarboxamide) salts. Synthesis and kinetics of light emission. J Biolumin Chemilumin. 6:(2):1991;107-114.
33. 125I-radioligands in the radioimmunoassay of progesterone. Steroids. 32:(4):1978;467-486.
34. Kundu N., Keenan S., Slaunwhite W.R. , Jr. Production of antiserums against contraceptive steroids. Steroids. 30:(1):1977;85-98.
35. Adamczyk M., Chen Y.Y., Fishpaugh J.R., Gebler J.C. Preparation and high-performance liquid chromatographic analysis of syn and anti isomers of steroidal 3-(O-carboxymethyl)oximes. J Chromatogr A. 657:(2):1993;345-348.
36. Mappus E, Grenot C, Forest M. Syn-anti geometric isomerism of α,β-unsaturated oximes and O-carboxymethyloximes at the C-3 and C-7 positions of steroids. Preparation of antigens bearing steroidal haptens with an established configuration. C R Hebd Seances Acad Sci, Ser C 1975;281(5-8):247-50.
37. Mitsuma M., Kambegawa A., Okinaga S., Arai K. A sensitive bridge heterologous enzyme immunoassay of progesterone using geometrical isomers. J Steroid Biochem. 28:(1):1987;83-88.