Inhibition of growth of Leishmania donovani promastigotes by newly synthesized 1,3,4-thiadiazole analogs

Saudi Pharmaceutical Journal

Volumn 17, Issue 3, 2009, Pages 227-232

  Al Qahtani, Ahmed ^a   Siddiqui, Yunus M ^a   Bekhit, Adnan A ^b   El Sayed, Ola A ^b   Aboul Enein, Hassan Y ^c   Al Ahdal, Mohammed N ^a  

^a KING FAISAL SPECIALIST HOSPITAL AND RESEARCH CENTER   (Saudi Arabia)

^b Alexandria University Faculty of Pharmacy   (Egypt)

^c NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Antileishmanial; Antiparasite; Leishmania donovani; Thiadiazoles

Indexed keywords

1 (2,5 DIMETHOXYBENZYLIDENE) 4 (4 CHLOROPHENYL)THIOSEMICARBAZIDE; 1 (2,5 DIMETHOXYBENZYLIDENE) 4 PHENYLTHIOSEMICARBAZIDE; 1 (2,5 DIMETHOXYBENZYLIDENE) 4 PTOLYLTHIOSEMICARBAZIDE; 1,3,4 THIADIAZOLE DERIVATIVE; 2 (4 TOLYLAMINO) 5 (2,5 DIHYDROXYPHENYL) 1,3,4 THIADIAZOLE; 2 PHENYLAMINO 5 (2,5 DIHYDROXYPHENYL) 1,3,4 THIADIAZOLE; 2 PHENYLAMINO 5 (2,5 DIMETHOXYPHENYL) 1,3,4 THIADIAZOLE; AMPHOTERICIN B; N (4 ACETYL 4,5 DIHYDRO 5 (2,5 DIHYDROXYPHENYL) 1,3,4 THIADIAZOL 2 YL) N PHENYLACETAMIDE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; IN VITRO STUDY; INFECTION CONTROL; LEISHMANIA DONOVANI; NONHUMAN; PROMASTIGOTE; VISCERAL LEISHMANIASIS;

EID: 72249119020     PISSN: 13190164     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsps.2009.08.005     Document Type: Article

References (36)

1. Abdo M.G., Elamin W.M., Khalil E.A., and Mukhtar M.M. Antimony-resistant Leishmania donovani in eastern Sudan: incidence and in vitro correlation. East Mediterr. Health J. 9 4 (2003) 837-843
2. Al-Qahtani A., Siddiqui Y.M., Bekhit A.A., Sayed O.A., Aboul-Enien H.Y., and Al-Ahdal M.N. Effect of Pyrazoloquinoline derivatives on the growth of Leishmania donovani promastigotes. Arch. Pharm. (Weinheim) 338 10 (2005) 484-487
3. Arevalo I., Ward B., Miller R., Meng T.C., Najar E., and Alvarez E. Successful treatment of drug resistant cutaneous leishmaniasis in humans by use of imiquimod, an immunomodulator. Clin. Infect. Dis. 33 (2001) 1847-1851
4. Behrouzi-Fardmoghadam M., Poorrajab F., Ardestani S.K., Emami S., Shafiee A., and Foroumadi A. Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines. Bioorg. Med. Chem. 16 8 (2008) 4509-4515
5. Berman J. Recent developments in leishmaniasis: epidemiology, diagnosis, and treatment. Curr. Infect. Dis. Rep. 7 (2005) 33-38
6. Bouteille B., Marie-Daragon A., Chauviere G., de Albuquerque C., Enanga B., Darde M.L., Vallat J.M., Perie J., and Dumas M. Effect of megazol on Trypanosoma brucei acute and subacute infections in Swiss mice. Acta Trop. 60 2 (1995) 73-80
7. Cassel D., Shoubi S., Glusman G., Cukierman E., Rotman M., and Zilberstein D. Leishmania donovani: characterization of a 38 kDa membrane protein that cross-reacts with the mammalian G-protein transducin. Exp. Parasitol. 72 4 (1991) 411-417
8. Chaaban I., El-Khawass E., Ran M., El-Sayed O., El-Saidi H., and Aboul-Enein H. Design, synthesis and in vitro evaluation of cytotoxic activity of new substituted 1,4-benzoquinones and hydroquinones. Med. Chem. Res. 16 (2007) 49-77
9. Cory A.H., Owen T.C., Barltrop J.a., and Cory J.G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth in culture. Cancer Commun. 3 (1991) 207-212
10. da Silva E.F., Canto-Cavalheiro M.M., Braz V.R., Cysne-Finkelstein L., Leon L.L., and Echevarria A. Synthesis, and biological evaluation of new 1,3,4-thiadiazolium-2-phenylamine derivatives against Leishmania amazonensis promastigotes and amastigotes. Eur. J. Med. Chem. 37 12 (2002) 979-984
11. Davis A.J., and Kedzierski L. Recent advances in antileishmanial drug development. Curr. Opin. Invest. Drugs 6 2 (2005) 163-169
12. Enanga B., Ariyanayagam M.R., Stewart M.L., and Barrett M.P. Activity of megazol, a trypanocidal nitroimidazole, is associated with DNA damage. Antimicrob Agents Chemother 47 10 (2003) 3368-3370
13. Faraut-Gambarelli F., Piarroux R., Deniau M., Giusiano B., Marty P., Michel G., Faugere B., and Dumon H. In vitro and in vivo resistance of Leishmania infantum to meglumine antimoniate: a study of 37 strains collected from patients with visceral leishmaniasis. Antimicrob. Agents Chemother. 41 (1997) 827-830
14. Fawzi A.B., Macdonald D., Benbow L.L., Smith-Torhan A., Zhang H., Weig B.C., HO G., Tulshian D., Linder M.E., and Graziano M.P. SCH-202676: an allosteric modulator of both agonist and antagonist binding to G protein-coupled receptors. Mol. Pharmacol. 59 1 (2001) 30-37
15. Foroumadi A., Emami S., Pournourmohammadi S., Kharazmi A., and Shafiee A. Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-5-substituted-1,3,4-thiadiazole derivatives. Eur. J. Med. Chem. 40 12 (2005) 1346-1350
16. Foroumadi A., Pournourmohammadi S., Soltani F., Asgharian-Rezaee M., Dabiri S., Kharazmi A., and Shafiee A. Synthesis and in vitro leishmanicidal activity of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles. Bioorg. Med. Chem. Lett. 15 8 (2005) 1983-1985
17. Fu G., Melville S., Brewster S., Warner J., and Barker D.C. Analysis of the genomic organisation of a small chromosome of Leishmania braziliensis M2903 reveals two genes encoding GTP-binding proteins, one of which belongs to a new G-protein family and is an antigen. Gene 210 2 (1998) 325-333
18. Gadad A.K., Mahajanshetti C.S., Nimbalkar S., and Raichurkar A. Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3, 4-thiadiazole-2-sulfonamide derivatives. Eur. J. Med. Chem. 35 9 (2000) 853-857
19. Goblyos A., de Vries H., Brussee J., and Ijzerman A.P. Synthesis and biological evaluation of a new series of 2,3,5-substituted [1,2,4]-thiadiazoles as modulators of adenosine A1 receptors and their molecular mechanism of action. J. Med. Chem. 48 4 (2005) 1145-1151
20. Hanasaki Y., Watanabe H., Katsurra K., Takayama H., Shirakawa S., Yamaguchi K., Sakai S., Ijichi K., and Fujiwara M. Thiadiazole derivatives: high potent specific HIV-1. Reverse transcriptase inhibitors. J. Med. Chem. 38 (1995) 2038-2040
21. Hansen B.D., Chiang P.K., and Perez-Arbelo J. Evidence for a membrane adenosine receptor in Leishmania mexicana (WR 227). Adv. Exp. Med. Biol. 195 (1986) 547-551
22. Henderson D.M., Sifri C.D., Rodgers M., Wirth D.F., Hendrickson N., and Ullman B. Multidrug resistance in Leishmania donovani is conferred by amplification of a gene homologous to the mammalian mdr1 gene. Mol. Cell Biol. 12 (1992) 2855-2865
23. Herwaldt B.L. Leishmaniasis. Lancet 354 9185 (1999) 1191-1199
24. Invidiata F.P., Simoni D., Scintu F., and Pinna N. 3,6-Disubstituted 1,2,4-triazolo[3,4-b][1,3,4] thiadiazoles: synthesis, antimicrobial and antiviral activity. II. Farmaco 51 (1996) 659-664
25. Kristanida M., Moroutsou A., Marakos P., Pouli N., Papakonstantinou-Garoufalias S., Pannecouque C., Witvrouw M., and Clercq E. Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)-1,2,4-triazolo[3,4-][1,3,4]thiadiazoles. Farmaco 50 (2002) 48-54
26. Lainson R., and Shaw J.J. Evolution, classification and geographical distribution. In: Killick P.W., and Kendrick R. (Eds). Leishmaniasis in Biology and Medicine (1987), Academic Press Ltd., London, England 848-907
27. Li Y., Xu Y., Qian X., and Qu B. Thiadiazole: a new family of intercalative photonuclease with electron transfer and radical mechanisms. Bioorg. Med. Chem. Lett. 13 20 (2003) 3513-3515
28. Maya J.D., Bollo S., Nunez-Vergara L.J., Squella J.A., Repetto Y., Morello A., Perie J., and Chauviere G. Trypanosoma cruzi: effect and mode of action of nitroimidazole and nitrofuran derivatives. Biochem. Pharmacol. 65 6 (2003) 999-1006
29. Paredes R., Munoz J., Diaz I., Domingo P., Gurgui M., and Clotet B. Leishmaniasis in HIV infection. J. Postgrad. Med. 49 1 (2003) 39-49
30. Poorrajab F., Ardestani S.K., Emami S., Behrouzi-Fardmoghadam M., Shafiee A., and Foroumadi A. Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: synthesis and in vitro biological evaluation. Eur. J. Med. Chem. (2008) April 9, Epub ahead of print
31. Pratlong F., Dereure J., Deniau M., Marty P., Faraut-Gambarelli F., and Dedet J.P. Enzymatic polymorphism during Leishmania/HIV co-infection: a study of 381 strains received between 1986 and 2000 at the international cryobank in Montpellier, France. Ann. Trop. Med. Parasitol. 97 Suppl. 1 (2003) S47-S56
32. Rioux J.A., Lanotte G., Serres E., Pratlong F., Bastien P., and Perieres J. Taxonomy of Leishmania. Use of isoenzymes. Suggestions for a new classification. Ann. Parasitol. Hum. Comp. 65 3 (1990) 111-125
33. Santos D.O., Coutinho C.E., Madeira M.F., Bottino C.G., Vieira R.T., Nascimento S.B., Bernardino A., Bourguignon S.C., Corte-Real S., Pinho R.T., Rodrigues C.R., and Castro H.C. Leishmaniasis treatment-a challenge that remains: a review. Parasitol. Res. (2008) April 4, Epub ahead of print
34. Singh S., and Sivakumar R. Challenges and new discoveries in the treatment of leishmaniasis. J. Infect. Chemother. 10 6 (2004) 307-315
35. van Muijlwijk-Koezen J.E., Timmerman H., Vollinga R.C., Frijtag von Drabbe Kunzel J., de Groote M., Visser S., and IJzerman A.P. Thiazole and thiadiazole analogues as a novel class of adenosine receptor antagonists. J. Med. Chem. 44 5 (2001) 749-762
36. Wolday D., Berhe N., Akuffo H., and Britton S. Leishmania-HIV interaction: immunopathogenic mechanisms. Parasitol. Today 15 5 (1999) 182-187