Two series of new semisynthetic triterpene derivatives: Differences in anti-malarial activity, cytotoxicity and mechanism of action

Malaria Journal

Volumn 12, Issue 1, 2013, Pages

  Da Silva, Gloria N S ^a,b   Maria, Nicole R G ^a   Schuck, Desirée C ^b   Cruz, Laura N ^b   De Moraes, Miriam S ^b   Nakabashi, Myna ^b   Graebin, Cedric ^c   Gosmann, Grace ^a   Garcia, Célia R S ^b   Gnoatto, Simone C B ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

haematin; Anti malarial; Betulinic acid; Mitochondrial membrane potential; Plasmodium falciparum; Semisynthesis; Ursolic acid

Indexed keywords

ATOVAQUONE; BETULIC ACID; HEMATIN; QUININE; TRITERPENE DERIVATIVE; URSOLIC ACID;

ANTIMALARIAL ACTIVITY; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MAMMAL CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; NONHUMAN; PLASMODIUM FALCIPARUM;

ANTIMALARIALS; CELL LINE; CELL SURVIVAL; EPITHELIAL CELLS; HUMANS; PLASMODIUM FALCIPARUM; TRITERPENES;

EID: 84874738544     PISSN: None     EISSN: 14752875     Source Type: Journal    
DOI: 10.1186/1475-2875-12-89     Document Type: Article

References (26)

1. PfEMP1: an antigen that plays a key role in the pathogenicity and immune evasion of the malaria parasite Plasmodium falciparum. Pasternak ND, Dzikowski R, Int J Biochem Cell Biol 2009 41 1463 1466 10.1016/j.biocel.2008.12.012 19150410
2. The malaria parasite Plasmodium falciparum: cell biological peculiarities and nutritional consequences. Baumeister S, Winterberg M, Przyborski JM, Lingelbach K, Protoplasma 2010 240 3 12 10.1007/s00709-009-0090-3 19949823
3. Natural products as antiparasitic drugs. Kayser O, Kiderlen AF, Croft SL, Parasitol Res 2003 90 Suppl 2 55 S62 12937967
4. Survey of resistance to chloroquine of falciparum and vivax malaria in Palawan, The Philippines. Baird JK, Caneta-Miguel E, Masbar S, Bustos DG, Abrenica JA, Layawen AV, Calulut JM, Leksana B, Wignall FS, Trans R Soc Trop Med Hyg 1996 90 413 414 10.1016/S0035-9203(96)90528-3 8882192
5. Antimalarials and the fight against malaria in Brazil. Carmargo LM, De Oliveira S, Basano S, Garcia CR, Ther Clin Risk Manag 2009 5 311 317 19753125
6. Novel approaches to antimalarial drug discovery. Biot C, Chibale K, Infect Disord Drug Targets 2006 6 173 204 10.2174/187152606784112155 16789878
7. Hypericum lanceolatum (Hypericaceae) as a potential source of new anti-malarial agents: a bioassay-guided fractionation of the stem bark. Zofou D, Kowa TK, Wabo HK, Ngemenya MN, Tane P, Titanji VP, Malar J 2011 10 167 10.1186/1475-2875-10-167 21682873
8. Betulinic acid and its derivatives: a review on their biological properties. Yogeeswari P, Sriram D, Curr Med Chem 2005 12 657 666 10.2174/0929867053202214 15790304
9. New betulinic acid derivatives as potent proteasome inhibitors. Qian K, Kim SY, Hung HY, Huang L, Chen CH, Lee KH, Bioorg Med Chem Lett 2011 21 5944 5947 10.1016/j.bmcl.2011.07.072 21856154
10. In vitro and in vivo evaluation of betulinic acid as an antimalarial. Steele JC, Warhurst DC, Kirby GC, Simmonds MS, Phytother Res 1999 13 115 119 10.1002/(SICI)1099-1573(199903)13:2<115::AID-PTR404>3.0.CO;2-1 10190183
11. Pharmacology of oleanolic acid and ursolic acid. Liu J, J Ethnopharmacol 1995 49 57 68 10.1016/0378-8741(95)90032-2 8847885
12. Antimalarial activity of four plants used in traditional medicine in Mali. Traore-Keita F, Gasquet M, Di Giorgio C, Ollivier E, Delmas F, Keita A, Doumbo O, Balansard G, Timon-David P, Phytother Res 2000 14 45 47 10.1002/(SICI)1099-1573(200002)14:1<45::AID-PTR544>3.0.CO;2-C 10641048
13. Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl) piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Gnoatto SC, Susplugas S, Dalla Vechia L, Ferreira TB, Dassonville-Klimpt A, Zimmer KR, Demailly C, Da Nascimento S, Guillon J, Grellier P, Verli H, Gosmann G, Sonnet P, Bioorg Med Chem 2008 16 771 782 10.1016/j.bmc.2007.10.031 17967541
14. Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite. Srivastava IK, Rottenberg H, Vaidya AB, J Biol Chem 1997 272 3961 3966 10.1074/jbc.272.7.3961 9020100
15. Haemozoin: from melatonin pigment to drug target, diagnostic tool, and immune modulator. Hanscheid T, Egan TJ, Grobusch MP, Lancet Infect Dis 2007 7 675 685 10.1016/S1473-3099(07)70238-4 17897610
16. Chemistry, biological activity, and chemo-therapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. Cichewicz RH, Kouzi SA, Med Res Rev 2004 24 90 114 10.1002/med.10053 14595673
17. Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents. Yu D, Sakurai Y, Chen CH, Chang FR, Huang L, Kashiwada Y, Lee KH, J Med Chem 2006 49 5462 5469 10.1021/jm0601912 16942019
18. Human malaria parasites in continuous culture. Trager W, Jensen JB, Science 1976 193 673 675 10.1126/science.781840 781840
19. Synchronization of Plasmodium falciparum erythrocytic stages in culture. Lambros C, Vanderberg JP, J Parasitol 1979 65 418 420 10.2307/3280287 383936
20. Triterpenoids as inhibitors of erythrocytic and liver stages of Plasmodium infections. Ramalhete C, Da Cruz FP, Lopes D, Mulhovo S, Rosario VE, Prudencio M, Ferreira MJ, Bioorg Med Chem 2011 19 7474 7481 10.1016/j.bmc.2011. 10.044 22071523
21. Experimental conditions for testing the inhibitory activity of chloroquine on the formation of beta-hematin. Baelmans R, Deharo E, Munoz V, Sauvain M, Ginsburg H, Exp Parasitol 2000 96 243 248 10.1006/expr.2000.4558 11162377
22. Antiplasmodial constituents of Cajanus cajan. Duker-Eshun G, Jaroszewski JW, Asomaning WA, Oppong-Boachie F, Brogger Christensen S, Phytother Res 2004 18 128 130 10.1002/ptr.1375 15022164
23. Biological activity of Anthraquinones and Triterpenoids from Prismatomeris fragrans. Kanokmedhakul K, Kanokmedhakul S, Phatchana R, J Ethnopharmacol 2005 100 284 288 10.1016/j.jep.2005.03.018 15885942
24. Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda. Fotie J, Bohle DS, Leimanis ML, Georges E, Rukunga G, Nkengfack AE, J Nat Prod 2006 69 62 67 10.1021/np050315y 16441070
25. Inhibitory effect of ursolic acid derivatives on hydrogen peroxide- and glutathione-mediated degradation of hemin: a possible additional mechanism of action for antimalarial activity. Mullie C, Jonet A, Dassonville-Klimpt A, Gosmann G, Sonnet P, Exp Parasitol 2010 125 202 207 10.1016/j.exppara.2010.01. 016 20109452
26. Comparison of the effect of mitochondrial inhibitors on mitochondrial membrane potential in two different cell lines using flow cytometry and spectrofluorometry. Kalbacova M, Vrbacky M, Drahota Z, Melkova Z, Cytometry A 2003 52 110 116 12655654