Synthesis and Antitubulin Activity of N1- and N 4-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania

Journal of Medicinal Chemistry

Volumn 47, Issue 7, 2004, Pages 1823-1832

  Bhattacharya, Gautam ^a   Herman, Johnathan ^a   Delfín, Dawn ^a   Salem, Manar M ^a   Barszcz, Todd ^a   Mollet, Mike ^a   Riccio, Guy ^b   Brun, Reto ^b   Werbovetz, Karl A ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; ANTIPROTOZOAL AGENT; N1 PHENYL 3,5 DINITRO N4,N4 DI N BUTYLSULFANILAMIDE; N1 PHENYL 3,5 DINITRO N4,N4 DI N PROPYLSULFANILAMIDE; SULFANILAMIDE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

AMASTIGOTE; ANTIPROTOZOAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; FLOW CYTOMETRY; LEISHMANIA; LEISHMANIA DONOVANI; MAMMAL CELL; NONHUMAN; TRYPANOSOMA; TRYPANOSOMA BRUCEI;

ANIMALS; CELL LINE; LEISHMANIA DONOVANI; STRUCTURE-ACTIVITY RELATIONSHIP; SULFANILAMIDES; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TUBULIN; TUBULIN MODULATORS;

EID: 1642333024     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0304461     Document Type: Article

References (19)

1. Werbovetz, K. Promising therapeutic targets for antileishmanial drugs. Expert Opin. Ther. Targets 2002, 6, 407-422.
2. Burchmore, R.; Ogbunude, P.; Enanga, B.; Barrett, M. Chemotherapy of human African trypanosomiasis. Curr. Pharm. Des. 2002, 8, 256-267.
3. Croft, S.; Seifert, K.; Duchene, M. Antiprotozoal activities of phospholipid analogs. Mol. Biochem. Parasitol. 2003, 126, 165-172.
4. Legros, D.; Ollivier, G.; Gastellu-Etchegorry, M.; Paquet, C.; Burri, C. ; et al. Treatment of human African trypanosomiasis-present situation and needs for research and development. Lancet Infect. Dis. 2002, 2, 437-440.
5. Jordan, A.; Hadfield, J.; Lawrence, N.; McGown, A. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med. Res. Rev. 1998, 18, 259-296.
6. Lacey, E. Mode of action of benzimidazoles. Parasitol. Today 1990, 6, 112-115.
7. Werbovetz, K.; Brendle, J.; Sackett, D. Purification, characterization, and drug susceptibility of tubulin from Leishmania. Mol. Biochem. Parasitol. 1999, 98, 53-65.
8. MacRae, T. H.; Gull, K. Purification and assembly in vitro of tubulin from Trypanosoma brucei brucei. Biochem. J. 1990, 265, 87-93.
9. Chan, M.; Fong, D. Inhibition of Leishmanias but not host macrophages by the antitubulin herbicide trifluralin. Science 1990, 249, 924-926.
10. Chan, M.; Triemer, R. E.; Fong, D. Effect of the anti-microtubule drug oryzalin on growth and differentiation of the parasitic protozoan Leishmania mexicana. Differentiation 1991, 46, 15-21.
11. Bhattacharya, G.; Salem, M.; Werbovetz, K. Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin. Bioorg. Med. Chem. Lett. 2002, 12, 2395-2398.
12. Werbovetz, K.; Sackett, D.; Delfin, D.; Bhattacharya, G.; Salem, M.; et al. Selective antimicrotubule activity of N1-phenyl-3,5-dinitro-N4,N4-di-n-propylsulfonilamide (GB-II-5) against kinetoplastid parasites. Mol. Pharmacol. 2003, 64, 1325-1333.
13. Schultz, H. 2,6-Dinitroaniline. In Organic Syntheses; Rabjohn, N., Ed.; John Wiley & Sons: New York, 1963; pp 364-366.
14. 2+ signalling, cytotoxicity and antitumor activity of the herbicide oryzalin and its analogs. Cancer Chemother. Pharmacol. 1997, 41, 22-28.
15. Zweig, G.; Sherma, J. Government regulations, pheromone analysis, additional pesticides. In Analytical Methods for Pesticides and Plant Growth Regulators; Zweig, G., Ed.; Academic Press: New York, 1976; pp 433-442.
16. Havens, C.; Bryant, N.; Asher, L.; Lamoreaux, L.; Perfetto, S.; et al. Cellular effects of leishmanial tubulin inhibitors on L. donovani. Mol. Biochem. Parasitol. 2000, 110, 223-236.
17. Hirumi, H.; Hirumi, K. Continuous cultivation of Trypanosoma brucei bloodstream forms in a medium containing a low concentration of serum proteins without feeder layer cells. J. Parasitol. 1989, 75, 985-989.
18. Ellis, J.; Fish, W.; Sileghem, M.; McOdimba, F. A colorimetric assay for trypanosome viability and metabolic function. Vet. Parasitol. 1993, 50, 143-149.
19. Kaminsky, R.; Brun, R. In vitro and in vivo activities of trybazine hydrochloride against various pathogenic trypanosome species. Antimicrob. Agents Chemother. 1998, 42, 2858-2862.