O-(fluoresceinylmethyl)hydroxylamine (OFMHA): A reagent for the preparation of fluorescent O-(fluoresceinylmethyl)oxime (FMO)-steroid conjugates

Steroids

Volumn 64, Issue 4, 1999, Pages 283-290

  Adamczyk, MacIej ^a   Chen, Yon Yih ^a   Grote, Jonathan ^a   Mattingly, Phillip G ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Fluorescein steroid conjugates; O (fluoresceinylmethyl)hydroxylamine; Tracers

Indexed keywords

ALDEHYDE DERIVATIVE; DIGITOXIN; ESTRONE; ESTRONE 17 (6 FLUORESCEINYLMETHYL)OXIME; HYDROCORTISONE; HYDROXYLAMINE; NORETHINDRONE 3 (6 FLUORESCEINYLMETHYL)OXIME; NORETHISTERONE; OXIME DERIVATIVE; PROGESTERONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIGITOXIN; ESTRADIOL; ESTRONE; FLUORESCEINS; FLUORESCENT DYES; HYDROCORTISONE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; NORETHINDRONE; OXIMES; PROGESTERONE; STEROIDS;

EID: 0032984265     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(99)00004-5     Document Type: Article

References (38)

1. 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.
2. Hosoda H., Sakai Y., Yoshida H., Miyairi S., Ishii K., Nambara T. Studies on steroids. Part CXLIII. The preparation of steroid N-hydroxysuccinimide esters and their reactivities with bovine serum albumin. Chem Pharm Bull. 27:(3):1979;742-746.
3. Stalla G.K., Giesemann G., Mueller O.A., Wood W.G., Scriba P.C. The development of a direct homologous radioimmunoassay for serum cortisol. J Clin Chem Clin Biochem. 19:(7):1981;427-434.
4. Shipchandler M.T., Fino J.R., Klein L.D., Kirkemo C.L. 4′-[Aminomethyl] fluorescein and its N-alkyl derivatives useful reagents in immunodiagnostic techniques . Anal Biochem. 162:(1):1987;89-101.
5. 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.
6. Allen R.M., Redshaw M.R. The use of homologous and heterologous 125I-radioligands in the radioimmunoassay of progesterone. Steroids. 32:(4):1978;467-486.
7. Zorina A.D., Martynov V.F., Matyukhina L.G., Saltykova I.A. Synthesis of 20-(O-carboxymethyl)progesterone oxime. Zh Obshch Khim. 50:(1):1980;187-189.
8. Stalla G., Giesemann G., Mueller O.A., Wood W.G., Scriba P.C. Non-extractive and specific radioimmunoassay for cortisol Results using a pure cortisol C3 derivative for antigen and tracer production . Fresenius' Z Anal Chem. 301:(2):1980;129.
9. Dorobantu I., Cotarlea M., Iancu E.I. Characterization of antitestosterone antibodies by RIA method. Rev Roum Biochim. 31:(23):1994;127-131.
10. Ali E., Sengupta J., Dhar T.K. Sandwich immunoassay of small molecules. I. Investigation with testosterone as model hapten. J Immunol Methods. 147:(2):1992;173-179.
11. Mons S., Lebeau L., Mioskowski C. An efficient synthesis of 6-oxo-17β-estradiol and its O-carboxymethyl oxime. Synth Commun. 28:(2):1998;213-218.
12. Dean P.D.G., Rowe P.H., Exley D. Preparation of 6-oxoestriol 6-[O-(carboxymethyl)oxime]-bovine serum albumin conjugates. Steroids Lipids Res. 3:(23):1972;82-89.
13. Kuss E., Goebel R. Determination of estrogens by radioimmunoassay with antibodies to estrogen-C6-conjugates. I. Synthesis of estrone-, 17β-estradiol, and estriol-6-albumin conjugates. Steroids. 19:(4):1972;509-518.
14. Parl F.F., Wetherall N.T., Halter S., Schuffman S., Mitchell W.M. Comparison of histochemical and biochemical assays for estrogen receptor in human breast cancer cell lines. Cancer Res. 44:(1):1984;415-421.
15. Zheng H., Tong X.H., Mao F., Weng L.L. Synthesis of receptor reagent Estradiol-polyethyleneglycol-fluorescein isothiocyanate . Yaoxue Xuebao. 26:(5):1991;336-340.
16. Joyce B.G., Nicholson R.I., Morton M.S., Griffiths K. Studies with steroid-fluorescein conjugates on estrogen target tissues. Eur J Cancer Clin Oncol. 18:(11):1982;1147-1155.
17. Schaeffer J.R., Frickey P.H., Burdick B.A. Fluorescent labeled biological materials. Res Discl. 181:1979;231.
18. Dandliker W.B., Hicks A.N., Levison S.A., Brawn R.J. Fluorescein-labeled estradiol A probe for anti-estradiol . Res Commun Chem Pathol Pharmacol. 18:(1):1977;147-156.
19. Dandliker W.B., Hicks A.N., Levison S.A., Brawn R.J. A fluorescein-labeled derivative of estradiol with binding affinity towards cellular receptors. Biochem Biophys Res Commun. 74:(2):1977;538-544.
20. 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.
21. Ekeke G.I., Landon J., Edwards C.R.W., White G.W., Shridi F. Magnetizable solid-phase separation fluoroimmunoassay for total estriol in pregnancy serum. Clin Chim Acta. 109:(1):1981;31-37.
22. Adamczyk M, Chen Y-Y, Walling JA, James BD, Artrip SG. Reagents and methods for the detection and quantification of testosterone in fluid samples. PCT Int Appl WO 1995; 9504283 A1 19950209.
23. Fujibayashi Y., Takemura Y., Matsumoto K., Wada K., Yonekura Y., Konishi J., Yokoyama A. High myocardial accumulation of radioiodinated digoxin derivative A possible sodium, potassium-ATPase imaging agent . J Nucl Med. 33:(4):1992;545-549.
24. Tovey KC, Findlay JWA. Digoxin and digitoxin derivatives. Ger. Offen. Patent DE 1976; 2526984 19760108.
25. Wilkinson S. Biological reagent. US Patent 1976; 3954739 19760504.
26. Yoshida RA. Antienzyme termination in enzyme immunoassays. US Patent 1982; 4341866 A 19820727.
27. Kolosova A.Y., Yeremin S.A., Gavrilova Y.M., Yegorov A.M. Polarization fluoroimmunoassay of progesterone. Probl Endokrinol. 40:(4):1994;48-51.
28. Evrain C., Rajkowski K.M., Cittanova N., Jayle M.F. The preparation of three fluorescence-labeled derivatives of testosterone. Steroids. 35:(6):1980;611-619.
29. Mikola H., Hanninen E. Introduction of aliphatic amino and hydroxy groups to keto steroids using O-substituted hydroxylamines. Bioconjugate Chem. 3:(2):1992;182-186.
30. Rao B.R., Patrick T.B., Sweet F. Steroid-albumin conjugate interaction with steroid-binding proteins. Endocrinology. 106:(1):1980;356-362.
31. Lee SH. Cytochemical agents and methods for the detection of steroid hormone receptors in human tissues. U.S. Patent 1980; 4215102 19800729.
32. Bergqvist A., Carlstroem K., Ljungberg O. Histochemical localization of estrogen and progesterone receptors Evaluation of a method . J Histochem Cytochem. 32:(5):1984;493-500.
33. Janssens J.P., Pylyser K., Bekaert J., Roelens J., Stuyck J., Dekeyser L.J., Lauweryns J.M., De Loecker W. Biochemical and histochemical analysis of steroid hormone binding sites in human primary breast cancer. Cancer. 55:(11):1985;2600-2611.
34. Blackmore P.F., Neulen J., Lattanzio F., Beebe S.J. Cell surface-binding sites for progesterone mediate calcium uptake in human sperm. J Biol Chem. 266:(28):1991;18655-18659.
35. 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. 24:1998;3599-3602.
36. Kundu N., Keenan S., Slaunwhite W.R. Jr. Production of antiserums against contraceptive steroids. Steroids. 30:(1):1977;85-98.
37. 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.
38. 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.