Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-(ω-N,N-diethylaminoamyloxy)-4,5-difluoroxanthone

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 3, 2008, Pages 1174-1183

  Dodean, Rozalia A ^a,b   Kelly, Jane X ^b   Peyton, David ^a   Gard, Gary L ^a   Riscoe, Michael K ^b   Winter, Rolf W ^a,b  

^a PORTLAND STATE UNIVERSITY   (United States)

^b PORTLAND VA MEDICAL CENTER   (United States)

Author keywords

Fluoroxanthone; Heme binding; Malaria; Spectroscopic investigation of binding

Indexed keywords

3,6 BIS(EPSILON N,N DIETHYLAMINOAMYLOXY) 4,5 DIFLUOROXANTHONE; 3,6 BIS(OMEGA DIETHYLAMINOAMYLOXY)XANTHONE; CHLOROQUINE; HEME; MEFLOQUINE; QUININE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ANTIMALARIAL ACTIVITY; ARTICLE; BINDING AFFINITY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; FLUORINE NUCLEAR MAGNETIC RESONANCE; IC 50; NONHUMAN; PH; PLASMODIUM FALCIPARUM; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; ANTIMALARIALS; FLUORINE; HEME; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; SPECTROPHOTOMETRY; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHONES;

EID: 38849147095     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.083     Document Type: Article

References (23)

1. Chambers R.D., Hutchinson J., Batsanov A.S., Lehmann C.W., and Naumov D.Y. J. Chem. Soc., Perkin Trans. 1: Org. Bioorg. Chem. (1996) 2271-2275
2. Connors, K. A. Binding Constants-The measurement of Molecular Complex Stability: New York, NY, 1987.
3. Dolphin, D. The Porphyrins. Physical Chemistry, Part B: New York, NY, 1979; Vol. IV.
4. Dorn, A.; Vippagunta, S. R.; Matile, H.; Jaquet, C.; Vennerstrom, J. L.; Ridley, R. G.; Pharma Division, P.R.F.H.-L.R.L.B.S. Biochem. Pharmacol. 1998, 55(6), 727-736.
5. Greenwood, B.; Mutabingwa, T. 2002, 415, 670-672.
6. Ignatushchenko M., Winter R., and Riscoe M. Am. J. Trop. Med. Hyg. 62 (2000) 77-81
7. Ignatushchenko M.V., Winter R.W., Bachinger H.P., Hinrichs D.J., and Riscoe M.K. FEBS Lett. 409 (1997) 67-73
8. Kelly J.X., Winter R., Peyton D.H., Hinrichs D.J., and Riscoe M. Antimicrob. Agents Chemother. 46 (2002) 144-150
9. Knell, A. J. Malaria: A Publication of the Tropical Programme of the Welcome Trust: New York, NY, 1991.
10. Leed A., DuBay K., Ursos L.M., Sears D., De Dios A.C., and Roepe P.D. Biochemistry 4132 (2002) 10245-10255
11. Moreau S., Perly B., and Biguet J. Biochimie 64 (1982) 1015-1025
12. Moreau S., Perly B., Chachaty C., and Deleuze C. Biochim. Biophys. Acta 840 (1985) 107-116
13. Olliaro P.L., and Goldberg D.E. Parasitol. Today 11 (1995) 294-297
14. Portela C., Afonso C.M., Pinto M.M., and Ramos M.J. Bioorg. Med. Chem. 12 (2004) 3313-3321
15. Portela C., Afonso C.M.M., Pinto M.M.M., and Ramos M.J. FEBS Lett. 547 (2003) 217-222
16. Riscoe M., Kelly J.X., and Winter R. Curr. Med. Chem. 12 (2005) 2539-2549
17. Schamp N., and Verzele M. Bull. Soc. Chim. Belg. 73 (1964) 38-43
18. Smilkstein M., Sriwilaijaroen N., Kelly J.X., Wilairat P., and Riscoe M. Antimicrob. Agents Chemother. 48 (2004) 1803-1806
19. Sun W.-C., Gee K.R., Klaubert D.H., and Haugland R.P. J. Org. Chem. 62 (1997) 6469-6479
20. Wanzlick H.W., and Mohrmann S. Chem. Ber. 968 (1963) 2257-2258
21. Winter R.W., Kelly J.X., Smilkstein M.J., Dodean R., Bagby G.C., Rathbun R.K., Levin J.I., Hinrichs D., and Riscoe M.K. Exp. Parasitol. 114 (2006) 47-56
22. Xu Kelly J., Winter R., Riscoe M., and Peyton D.H. J. Inorg. Biochem. 86 (2001) 617-625
23. Ziegler J., Linck R., and Wright D.W. Curr. Med. Chem. 8 2 (2001) 171-189