Aryl phosphate derivatives of bromo-methoxy-azidothymidine are dual- function spermicides with potent anti-human immunodeficiency virus

Biology of Reproduction

Volumn 59, Issue 3, 1998, Pages 503-515

  D'Cruz, Osmond J ^a   Venkatachalam, T K ^a   Zhu, Zhaohai ^a   Shih, Mei Jue ^a   Uckun, Fatih M ^a  

^a Department of Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3' AZIDO 5 BROMO 6 METHOXY 3' DEOXYTHYMIDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; NONOXINOL 9; SPERMICIDAL AGENT; UNCLASSIFIED DRUG; ZIDOVUDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; FERTILITY; HIGH RISK PATIENT; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL; SEXUAL TRANSMISSION; SPERMATOZOON MOTILITY; TRANSMISSION ELECTRON MICROSCOPY; VAGINA EPITHELIUM; VIRUS REPLICATION; VIRUS TRANSMISSION;

CRICETINAE; HUMAN IMMUNODEFICIENCY VIRUS; SIA;

EID: 0031826304     PISSN: 00063363     EISSN: None     Source Type: Journal    
DOI: 10.1095/biolreprod59.3.503     Document Type: Article

References (44)

1. Osborn JE. Women and HIV/AIDS: the silent epidemic. Sex Info Educ Council US Rep 1991; 19:1-4.
2. Mann J, Tarantola D. The global AIDS pandemic. In: Velji AM (ed.), Infectious Disease Clinics of North America. Philadelphia: Saunders; 1995: 275-285.
3. Cellum CL, Watts DH. HIV and women. In: Spach DL, Hooten RM (eds.), The HIV Manual. New York: Oxford University Press; 1996: 120-127.
4. Center for Disease Control. Update: acquired immunodeficiency syndrome - United States. 1994. MMWR 1995; 44:64-67.
5. Ellerbrock TV, Bush TJ, Chamberland ME, Oxtoby MJ. Epidemiology of women with AIDS in the United States, 1981 through 1990. JAMA 1991; 265:2971-2975.
6. Alexander NJ. Sexual spread of HIV infection. Hum Reprod 1996; 11:111-120.
7. OTC Panel. Vaginal contraceptive drug products for over-the-counter human use. Fed Reg 1980; 45:82014-82049.
8. Chantier E. Vaginal spermicides: some current concerns. Br Family Planning 1992; 17:118-119.
9. Feldblum PJ, Fortney JA. Condoms, spermicides and transmission of human immunodeficiency virus: a review of the literature. Am J Public Health 1988; 78:52-54.
10. Feldblum P, Bernardik E, Rosenberg MJ. Spermicide use and sexually transmitted diseases. JAMA 1988; 259:2851.
11. Judson FN, Ehret JM, Bodin GF, Levin MJ, Rietmeiyer CA. In vitro evaluation of condoms with and without nonoxynol-9 as physical and chemical barriers against Chlamydia trachomatis, herpes simplex virus type 2, and human immunodeficiency virus. Sex Transm Dis 1989; 16:51-56.
12. Bird KD. The use of spermicide containing nonoxynol-9 in the prevention of HIV infections. AIDS 1991; 55:791-796.
13. Bourinbaiar AS, Lee-Huang S. Comparative in vitro study of contraceptive agents with anti-HIV activity: gramicidin, nonoxynol-9, and gossypol. Contraception 1994; 49:131-137.
14. Zeking L, Feldblum PJ, Oliver RM, Kaptue L. Barrier contraceptive use and HIV infection among high-risk women in Cameron. AIDS 1993; 7:725-731.
15. Rowe PM. Nonoxynol-9 fails to protect against HIV-1. Lancet 1997; 349:1074.
16. Niruthisard S, Roddy RE, Chutivongse S. The effects of frequent nonoxynol-9 use on the vaginal and cervical mucosa. Sex Transm Dis 1991; 18:176-179.
17. Roddy RE, Cordero M, Cordero C, Fortney JA. A dosing of nonoxynol-9 and genital irritation. Int J STD & HIV 1993; 4:165-170.
18. Weir SS, Roddy RE, Zekeng L, Feldblum PJ. Nonoxynol-9 use, genital ulcers, and HIV infection in a cohort of sex workers. Genitourin Med 1995; 71:78-81.
19. Tryphonas L, Buttar HS. Morphological evidence for vaginal toxicity of Delfan contraceptive cream in the rat. Toxicol Lett 1984; 20:289-295.
20. Kreiss J, Ngugi E, Holmes K, Ndinya AJ, Waiyaki P, Roberts PL, Ruminjo I, Ajabi R, Kimata J, Fleming TR, Anzala A, Holton D, Plummer F. Efficacy of nonoxynol-9 contraceptive sponge use in preventing heterosexual transmission of HIV in Nairobi prostitutes. JAMA 1992; 268:477-482.
21. Kumar R, Wang L, Wiebe LI, Knaus EE. Synthesis, in vitro biological stability, and anti-HIV activity of 5-halo-6-alkoxy (ROR azido)-5,6,-dihydro-3′-azido-3′-deoxythymidine diasteriomers as potential prodnigs to 3′-azido-3-deoxythymidine (AZT). J Med Chem 1994; 37: 4297-4306.
22. McGuigan C, Cahard D, Sheeka HM, De Clercq E, Balzarini J. Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite. J Med Chem 1996; 39:1748-1753.
23. McGuigan C, Pathirana RN, Mahmood N, Devine KG, Hay AJ. Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT. Antivir Res 1992; 17:311-321.
24. Zarling JM, Moran PA, Haffar O, Sias J, Richman DD, Spina CA, Myers DE, Kuebelbeck Y, Ledbetter JA, Uckun FM. Inhibition of HIV replication by pokeweed antiviral protein targeted to CD4+ cells by monoclonal antibodies. Nature 1990; 347:92-95.
25. Uckun FM, Chelstrom LM, Ahlgren-Tuel L, Dibirdik I, Irvin JD, Langlie M-C, Myers DE. TXU (Anti-CD7)-pokeweed antiviral protein as a potent inhibitor of human immunodeficiency virus. Antimicrob Agents Chemother 1998; 42:383-388.
26. 2-Integrin (CD11b/CD18) is the primary adhesive glycoprotein complex involved in neutrophil-mediated immune injury to human sperm. Biol Reprod 1995; 53:1118-1130.
27. D'Cruz OJ, Uckun FM. Vanadocenes as a new class of effective spermicides. Adv Reprod 1998; 1:101-123.
28. D'Cruz OJ, Haas GG. Flow cytometric quantitation of the expression of membrane cofactor protein as a marker for the human sperm acrosome reaction. Fertil Steril 1992; 58:633-636.
29. Earlandsen SL, Gould RP, Frethem C, Wells CL, Pawley J, Hamilton DW. Membrane fixation for high-resolution low-voltage SEM: Studies on Giardia, rat spermatozoa, and mouse macrophages. Scanning 1989; 11:169-175.
30. Stoffel MH, Frethem C, Hamilton DW, Friess AE. Improved preservation of rat epididymal sperm for high-resolution low-voltage scanning electron microscopy (HR-LVSEM). Mol Reprod Dev 1993; 34: 175-182.
31. Yanagimachi R, Yanagimachi H, Rogers BJ. The use of zona-free animal ova as a test system for the assessment of the fertilizing capacity of human spermatozoa. Biol Reprod 1976; 15:471-476.
32. El-Danasouri I, Milki A, Gebhardt J, Louie D, Westphal L. Fluorescence staining of nuclear deoxyribonucleic acid allows for accurate assessment of the hamster egg penetration assay. Fertil Steril 1993; 59:470-472.
33. Hogan B, Beddington R, Costantini F, Lacy E. Manipulating the Mouse Embryo. Plainview, NY: Cold Spring Harbor Laboratory Press; 1994.
34. Wilborn WH, Hahn DW, McGuire JJ. Scanning electron microscopy of human spermatozoa after incubation with the spermicide nonoxynol-9. Fertil Steril 1983; 39:717-719.
35. Schill WB, Wolf HH. Ultrastructure of human spermatozoa in the presence of the spermicide nonoxynol-9 and a vaginal contraceptive containing nonoxynol-9. Andrologia 1981; 13:42-49.
36. Alexander NJ. Future contraceptives. Sci Am 1995; 273:136-141.
37. Liu DY, Clarke GN, Lopata A. A sperm-zona pellucida binding test and in vitro fertilization. Fertil Steril 1989; 52:281-287.
38. Oehninger S, Mahony M, Ozgur K, Kolm P, Kruger T, Franken D, Clinical significance of human sperm-zona pellucida binding. Fertil Steril 1997; 67:1121-1127.
39. Overstreet JW, Yanagimachi R, Katz DF, Hayashi K, Hanson FW. Penetration of human spermatozoa into the human zona pellucida and the zona-free hamster egg: a study of fertile and infertile patients. Fertil Steril 1980; 33:534-542.
40. Ausmanas M, Tureck RW, Blasco L, Kopf GS, Ribas J, Mastrioanni L Jr. The zona-free hamster egg penetration assay as a prognostic indicator in a human in vitro fertilization. Fertil Steril 1985; 43:433-437.
41. Overstreet JW, Drobnis EZ. Sperm transport in the female tract. In: Barratt CLR, Cooke ID (eds.), Advances in Donor Insemination. Cambridge, UK: Cambridge University Press; 1993: 33-49.
42. Yanagimachi R. Mammalian fertilization. In: Knobil E, Neill J (eds.), The Physiology of Reproduction. New York: Raven Press; 1988: 135-185.
43. Liu DY, Lopata A, Johnston WIH, Baker HWG. A human sperm zona pellucida binding test using oocytes that failed to fertilize in vitro. Fertil Steril 1988; 50:782-788.
44. Levy R, Eustache F, Pilikian S, Clavel C, Cordonier H, Benchaib M, Lornage J, Pinatel M-C, Guerin JF. Effect of gastrin-releasing peptide on sperm functions. Mol Hum Reprod 1996; 2:867-872.