Redox-active dinitrodiphenylthioethers against Leishmania: Synthesis, structure-activity relationships and mechanism of action studies

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 2, 2009, Pages 820-829

  Delfín, Dawn A ^a   Morgan, Rachel E ^a   Zhu, Xiaohua ^a   Werbovetz, Karl A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Aromatic nitro groups; Leishmania; Mitochondrial membrane potential; Reactive oxygen species

Indexed keywords

2 [(2,4 DICHLORO 5 METHYLPHENYL)SULFANYL] 1,3 DINITRO 5 (TRIFLUOROMETHYL)BENZENE; 4 [(3,5 DINITROBENZONITRILE)SULFANYL]PHENYL METHYL ETHER; AROMATIC NITRO COMPOUND; BTB 06237; DINITRODIPHENYLTHIOETHER DERIVATIVE; REACTIVE OXYGEN METABOLITE; SULFIDE; UNCLASSIFIED DRUG;

AMASTIGOTE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; LEISHMANIA; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN; OXIDATION REDUCTION REACTION; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIPROTOZOAL AGENTS; CERCOPITHECUS AETHIOPS; LEISHMANIA DONOVANI; MACROPHAGES, PERITONEAL; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; MICE, INBRED STRAINS; OXIDATION-REDUCTION; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REACTIVE OXYGEN SPECIES; SULFIDES; VERO CELLS;

LEISHMANIA DONOVANI;

EID: 58549093170     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.031     Document Type: Article

References (44)

1. WHO: http://www.who.int/leishmaniasis/burden/en.
2. Croft S.L., Barrett M., and Urbina J. Trends Parasitol. 21 (2005) 508
3. Ouellette M., Drummelsmith J., and Papadopoulou B. Drug Resist. Updat. 7 (2004) 257
4. Singh S., and Sivakumar R. J. Infect. Chemother. 10 (2004) 307
5. Bhattacharya G., Herman J., Delfín D., Salem M.M., Barszcz T., Mollet M., Riccio G., Brun R., and Werbovetz K.A. J. Med. Chem. 47 (2004) 1823
6. Bhattacharya G., Salem M.M., and Werbovetz K.A. Bioorg. Med. Chem. Lett. 12 (2002) 2395
7. Werbovetz K.A., Sackett D.L., Delfín D., Bhattacharya G., Salem M., Obrzut T., Rattendi D., and Bacchi C. Mol. Pharmacol. 64 (2003) 1325
8. Delfín D., Bhattacharjee A.K., Yakovich A.J., and Werbovetz K. J. Med. Chem. 49 (2006) 4196
9. Kovacic P., and Becvar L.E. Curr. Pharm. Des. 6 (2000) 143
10. Kovacic P., and Osuna Jr. J.A. Curr. Pharm. Des. 6 (2000) 277
11. Kovacic P., Sacman A., and Wu-Weis M. Curr. Med. Chem. 9 (2002) 823
12. Moreno S.N.J., and Docampo R. Environ. Health Perspect. 64 (1985) 199
13. Kovacic P., Pozos R.S., Somanathan R., Shangari N., and O'Brien P.J. Curr. Med. Chem. 12 (2005) 2601
14. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
15. Ley S.V., and Thomas A.W. Angew. Chem. Int. Ed. Engl. 42 (2003) 5400
16. Buckner F.S., and Wilson A.J. Am. J. Trop. Med. Hyg. 72 (2005) 600
17. Adams G.E., Clarke E.D., Jacobs R.S., Stratford I.J., Wallace R.G., Wardman P., and Watts M.E. Biochem. Biophys. Res. Commun. 72 (1976) 824
18. Cénas N., and Ollinger K. Arch. Biochem. Biophys. 315 (1994) 170
19. Wardman P. Environ. Health Perspect. 64 (1985) 309
20. Hansch C., Leo A., and Taft R.W. Chem. Rev. 91 (1991) 165
21. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine (1999), Oxford University Press, Oxford
22. Uetrecht J. Drug Metab. Rev. 34 (2002) 651
23. 2 DCFDA search).
24. Maybridge. http://www.maybridge.com (Screening Collection/BTB06237 search).
25. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3
26. de Mecca M.M., Fanelli S.L., Bartel L.C., de Castro C.R., Diaz E.G., and Castro J.A. Life Sci. 81 (2007) 144
27. Chauviere G., Bouteille B., Enanga B., de Albuquerque C., Croft S.L., Dumas M., and Perie J. J. Med. Chem. 46 (2003) 427
28. Blumenstiel K., Schoneck R., Yardley V., Croft S.L., and Krauth-Siegel R.L. Biochem. Pharmacol. 58 (1999) 1791
29. Krauth-Siegel R.L., and Schoneck R. FASEB J. 9 (1995) 1138
30. Tsuhako M.A., Alves M.J.M., Colli W., Brener Z., and Augusto O. Biomed. Pharmacol. 38 (1989) 4491
31. Baliani A., Bueno G.J., Stewart M.L., Yardley V., Brun R., Barrett M.P., and Gilbert I.H. J. Med. Chem. 48 (2005) 5570
32. Docampo R. Chem. Biol. Interact. 73 (1990) 1
33. Sanz A.M., Gómez-Contreras F., Navarro P., Sánchez-Moreno M., Boutaleb-Charki S., Campuzano J., Pardo M., Osuna A., Cano C., Yunta M.J.R., and Campayo L. J. Med. Chem. 51 (2008) 1962
34. Checchi F., Piola P., Ayikoru H., Thomas F., Legros D., and Priotto G. PLoS Negl. Trop. Dis. 1 (2007) e64
35. Priotto G., Kasparian S., Ngouama D., Ghorashian S., Arnold U., Ghabri S., and Karunakara U. Clin. Infect. Dis. 45 (2007) 1435
36. Acros Organics. http://www.acros.com (2,4-dichloro-5-methylbenzenesulfonyl chloride search).
37. Maybridge. http://www.maybridge.com (Building Blocks Collection/SB00644 search).
38. Neidlein R., and Humburg G. Justus Liebigs Ann. Chem. (1977) 904
39. Bayer. France Patent, Patent No. FRXXBL FR 2008330 19700116, 1970, 12.
40. Wolfgang, B.; Kuehlein, K. Germany Patent, Patent No. GWXXBX DE 3216126 A1 19831103, 1983.
41. Malichenko B.F., Levchenko E.M., and Yaguposkii L.M. Ukrainskii Khimicheskii Zhurnal (Russ. Ed.) 33 (1967) 1273
42. Chamberlin R.A., and Crampton M.R. J. Chem. Soc., Perkins Trans. 2: Phys. Org. Chem. (1994) 425
43. D'Amico J.J., Tung C.C., Dahl W.E., and Dahm D.J. Phosphorus Sulfur 4 (1978) 267
44. Werbovetz K.A., Brendle J.J., and Sackett D.L. Mol. Biochem. Parasitol. 98 (1999) 53