Amberlite IRA 402(OH)-mediated synthesis and evaluation of fused tricyclic quinolinium salts as potent non-detergent type microbicidal spermicides

Medicinal Chemistry Research

Volumn 23, Issue 3, 2014, Pages 1488-1500

  Banerjee, Maitreyee ^a   Kumar, Shrabanti ^a   Ghosh, Soma ^b   Paira, Rupankar ^a   Mondal, Shyamal ^a   Karmokar, Sanmoy ^b   Chattopadhyay, Debprsad ^c   Bhadra, Rupak K ^a   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b JADAVPUR UNIVERSITY   (India)

^c INDIAN COUNCIL OF MEDICAL RESEARCH   (India)

Author keywords

Fused tricyclic oxazaquinolinium cations; Microbicides; Sander Cramer test; Scanning electron microscopy; Sperm immobilization; Spermicides

Indexed keywords

EID: 84893744164     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0758-2     Document Type: Article

References (42)

1. Aitken RJ, Buckingham D, Harkiss D (1993) Use of xanthine oxidase free radical generating system to investigate the cytotoxic effects of reactive oxygen species on human spermatozoa. J Reprod Fertil 97:441-450
2. Banerjee M, Kumar S, Paira R, Ghosh S, Karmokar S, Mondal N.B (2013) Synthesis and characterization of furo[3,2-h]quinoliniums as potent non-detergent spermicides. BSP Letters in Drug Design and Discovery, in press
3. Bharitkar YP, Banerjee M, Kumara S, Paira R, Meda R, Kuotsub K, Mondal Nirup B (2013) Search for a potent microbicidal spermicide from the isolates of Shorea robusta resin. Contraception 88:133-140
4. Bhowal SK, Lala S, Hazra A, Paira P, Banerjee S, Mondal NB, Chakrabarty S (2008) Synthesis and assessment of fertility regulating potential of 2-(2″-chloroacetamidobenzyl)-3-(3′-indolyl) quinoline in adult rats as a male contraceptive agent. Contraception 77:214-222
5. Chattopadhyay D, Dastidar SG, Chakrabarty AN (1988) Antibacterial property of methdilazine and its synergism with antibiotics and some chemotherapeutic agents. Arzneim Forsch 38(II):869-872
6. Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R (1998) Altered membrane permeability as the basis of bactericidal action of methdilazine. J Antimicrob Chemother 42:83-86
7. CLSI (2009) Methods for antifungal disk diffusion susceptibility testing of filamentous fungi; proposed guideline. CLSI documents M51-P. Clinical and Laboratory Standards Institute, Wayne
8. CLSI (2012) Performance standards for antimicrobial disk susceptibility tests; approved standard - eleventh edition M02-A11. Clinical and Laboratory Standards Institute, Wayne
9. D'Cruz OJ, Shih MJ, Yiv SH, Chen CL, Uckun FM (1999) Synthesis, characterization and preclinical formulation of a dual-action phenyl phosphate derivative of bromo-methoxy zidovudine (compound WHI-07) with potent anti-HIV and spermicidal activities. Mol Hum Reprod 5:421-432
10. Doncel GF (2006) Exploiting common targets in human fertilization and HIV infection: development of novel contraceptive microbicides. Hum Reprod Update 12:103-117
11. Flajshans M, Cosson J, Rodina M, Linhart O (2004) The application of image cytometry to viability assessment in dual fluorescence-stained fish spermatozoa. Int J Cell Biol 28:955-959
12. Hawes SE, Hillier SL, Benedetti J, Stevens CE, Koutsky LA, Hanssen P, Holmes K (1996) Hydrogen peroxide producing lactobacilli and acquisition of vaginal infections. J Infec Dis 174:1058-1063
13. ICPD '94: summary of the programme of action. International conference on population and development, United Nations, 1995. Available from http://www.un.org/ecosocdev/geninfo/populatin/icpd.htm. Accessed 5-13 Sep 1994
14. Jain RK, Maikhuri JP, Kiran KSTVS, Sharma VL, Dwivedi AK, Mitra K, Bajpai VK, Gupta G (2007) Novel disulphide esters of carbothioic acid as potent, non-detergent spermicides with low toxicity to Lactobacillus and HeLa cells in vitro. Hum Reprod 22:708-716
15. Jayendran RS, Van der Ven HH, Perag-Pelaez M, Crab BG, Zaneveld LJD (1984) Development of an assay to assess the functional integrity of the human sperm membrane and its relationship to other semen characteristics. J Reprod Fertil 70:219-228
16. Kanwar U, Anand RJK, Sanyal SN (1993) The effect of nifedipine, a calcium channel blocker, on human spermatozoal function. Contraception 48:453-470
17. Kempf C, Jentsch P, Barre-Sinoussi FB, Poirier B, Morgenthaler JJ, Morell A, Germann D (1991) Inactivation of human immunodeficiency virus (HIV) by low pH and pepsin. J Acquir Immune Defic Syndr 4:828-830
18. Khillare B, Shrivastav TG (2003) Spermicidal activity of Azadirachta indica 528(neem) leaf extract. Contraception 68:225-229
19. Kumar S, Biswas S, Mandal D, Roy HN, Chakraborty S, Kabir SN, Banerjee S, Mondal NB (2007) Chenopodium album seed extract:a potent sperm-immobilizing agent both in vitro and in vivo. Contraception 75:71-78
20. Kumar S, Chatterjee R, Dolai S, Adak S, Kabir SN, Banerjee S, Mondal NB (2008) Chenopodium album seed extract induced sperm cell death: exploration of a plausible pathway. Contraception 77:456-462
21. Kumar S, Naskar S, Hazra A, Sarkar S, Mondal NB, Banerjee S (2009) Evaluation of spermicidal potential of labdane diterpenes from Andrographis paniculata. Int J Biol Chem Sci 3:628-636
22. Kumar S, Biswas S, Banerjee S, Mondal NB (2011) Evaluation of safety margins of Chenopodium album seed decoction: 14-day subacute toxicity and microbicidal activity studies. Reprod Biol Endocrin 9:102-110
23. Martin HL, Richardson BA, Nyange PM, Lavreys L, Hillier SL, Chohan B, Mandaliya K et al (1999) Vaginal lactobacilli, microbial flora and risk of human immunodeficiency virus type 1 and sexually transmitted disease acquisition. J Infect Dis 180:1863-1868
24. Paira P, Hazra A, Kumar S, Paira R, Sahu KB, Naskar S, Saha P, Mondal S, Maity A, Banerjee S, Mondal NB (2009) Efficient synthesis of 3,3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential. Bioorg Med Chem Lett 19:4786-4789
25. Paira R, Paira P, Maity A, Mondal S, Hazra A, Sahu KB, Naskar S, Saha P, Banerjee M, Mondal NB (2010) Amberlite IRA 402(OH): an efficient mediator for the exclusive synthesis of fused tricyclic oxaza quinolinium salts. Tetrahedron Lett 51(24):513200-513204
26. Pal D, Chakraborty P, Ray HN, Pal BC, Mitra D, Kabir SN (2009) Acaciaside-B-enriched fraction of Acacia auriculiformis is a prospective spermicide with no mutagenic property. Reproduction 138:453-462
27. Palit P, Paira P, Hazra A, Banerjee S, Das Gupta A, Dastidar SG, Mondal NB (2009) Phase transfer catalysed synthesis of bis-quinolines: antileishmanial activity in experimental visceral Leishmaniasis and in vitro antibacterial evaluation. Eur J Med Chem 44:845-853
28. Pape W, Hoppe U (1991) In vitro methods for the assessment of primary local effects of topically applied preparations. Skin Pharmacol 4:205-212
29. Pape W, Pfannenbecker U, Hoppe U (1987) Validation of the red blood cell test system as in vitro assay for the rapid screening of irritation potential of surfactants. Mol. Toxicol 88:525-536
30. Ray S, Sadhukhan PK, Mondal NB, Mahato SB, Majumder HK (1997) Dual Inhibition of DNA Topoisomerases of Leishmania donovani by Novel Indolyl Quinolines. Biochem Biophys Res Commun 230:171-175
31. Renner R (1997) European bans on surfactant trigger transatlantic debate. Environ Sci Technol 31:A316-A320
32. Roddy RE, Zeking L, Ryan KA, Tamoufe U, Weir SS, Wong EL (1998) A controlled trial of nonoxynol 9 film to reduce male-to-female transmission of sexually transmitted diseases. N Engl J Med 339:504-510
33. Sahu KB, Banerjee M, Ghosh S, Maity A, Mondal S, Paira R, Hazra A, Karmakar S, Samanta A, Mondal NB (2013) I2 catalyzed Friedel-Crafts alkylation reaction of substituted anilines with ninhydrin: formation of novel products and their antimicrobial evaluation. Med Chem Res 22:2023-2037
34. Shah V, Doncel GF, Seyoum T, Eaton KM, Zalenskaya I, Hagver R, Azim A, Gross R (2005) Sophorolipids, Microbial glycolipids with anti-human immuno-deficiency virus and sperm-immobilizing activities. Antimicrob Agents Chemother 49:4093-4100
35. Sharma SK, SaiRam M, Ilvazhagan G, Devendra K, Shivaji SS, Selvamurthy W (1996) Mechanism of action of NIM-76: a novel vaginal contraceptive from neem oil. Contraception 54:373-378
36. Singh KK, Parmar S, Tatke PA (2012) Contraceptive efficacy and safety of HerbOshield™ vaginal gel in rats. Contraception 85:122-127
37. Thiele B, Gunther K, Schwuger M (1997) Alkylphenol ethoxylates trace analysis and environmental behavior. Chem Rev 97:3247-3272
38. United Nations Population Fund (2011) State of the world population 2011. New York: UNFPA. Available from http://www.unfpa.org/swp/. Accessed 17 Oct 2011
39. Va′squez A, Jakobsson T, Ahrne S, Forsum U, Molin G (2002) Vaginal Lactobacillus flora of healthy Swedish women. J Clin Microbiol 40:2746-2749
40. Wang C (2012) History of the Chinese Family Planning Program: 1970-2010. Contraception 85:563-569
41. Wilborn WH, Hahn DW, McGuire JJ (1983) Scanning electron microscopy of human spermatozoa after incubation with the spermicide nonoxynol-9. Fertil Steril 39:717-719
42. Yu K, Chien YW (1995) Spermicidal activity-structure relationship of nonoxynol oligomers: physicochemical basis. Int J Pharmaceut. 125:81-90