Antiprotozoal, anticancer and antimicrobial activities of dihydroartemisinin acetal dimers and monomers

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 23, 2009, Pages 7949-7957

  Slade, Desmond ^a   Galal, Ahmed M ^a   Gul, Waseem ^a,b   Radwan, Mohamed M ^a   Ahmed, Safwat A ^a,c   Khan, Shabana I ^a   Tekwani, Babu L ^a   Jacob, Melissa R ^a   Ross, Samir A ^a,d   ElSohly, Mahmoud A ^a,b,d  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b ElSohly Laboratories Incorporated   (United States)

^c Suez Canal University   (Egypt)

^d UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Acetal monomers; Antibacterial activity; Anticancer activity; Antifungal activity; Antileishmanial activity; Antimalarial activity; Artemisia annua; Artemisinin; Dihydroartemisinin; dimers and trimers

Indexed keywords

AMPHOTERICIN B; ARTEMISININ; CHLOROQUINE; DIHYDROARTEMISININ DERIVATIVE; DOXORUBICIN;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CRYPTOCOCCUS NEOFORMANS; NONHUMAN; PLASMODIUM FALCIPARUM;

ACETALS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIPROTOZOAL AGENTS; ARTEMISININS; CELL LINE, TUMOR; CRYPTOCOCCUS NEOFORMANS; DIMERIZATION; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; PLASMODIUM FALCIPARUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ARTEMISIA ANNUA; FILOBASIDIELLA NEOFORMANS; PLASMODIUM FALCIPARUM;

EID: 71849116549     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.019     Document Type: Article

References (54)

1. Pierce S.K., and Miller L.H. J. Immunol. 182 (2009) 5171
2. Rosenthal P.J. N. Eng. J. Med. 358 (2008) 1829
3. White N.J. Science 320 (2008) 330
4. Genton B. Expert Rev. Vaccines 7 (2008) 597
5. Vekemans J., and Ballou W.R. Expert Rev. Vaccines 7 (2008) 223
6. Turschner S., and Efferth T. Mini-Rev. Med. Chem. 9 (2009) 206
7. Edwards G., and Biagini G.A. Br. J. Clin. Pharmacol. 61 (2006) 690
8. Aweeka F.T., and German P.I. Clin. Pharmacokinet. 47 (2008) 91
9. Plowe C.V. Clin. Infect. Dis. 44 (2007) 1075
10. Kindermans J.-M., Pilloy J., Olliaro P., and Gomes M. Malar. J. 6 (2007)
11. Efferth T. Planta Med. 73 (2007) 299
12. Namdeo A.G., Mahadik K.R., and Kadam S.S. Phcog Mag. 2 (2006) 106
13. Gomes M., Ribeiro I., Warsame M., Karunajeewa H., and Petzold M. BMC Infect. Dis. 8 (2008) 1
14. Rydén A.-M., and Kayser O. Chemistry, Biosynthesis and Biological Activity of Artemisinin and Related Natural Peroxides. In: Gupta R.R., and Khan M.T.H. (Eds). Bioactive Heterocycles III (Topics in Heterocyclic Chemistry) Vol. 9 (2007), Springer, Berlin, Heidelberg 1-31
15. Sharma V.P. Curr. Sci. 90 (2006) 1323
16. Pasvol G. Br. Med. Bull. 75-76 (2005) 29
17. Guidelines for the treatment of malaria. Global Malaria Programme. World Health Organization 2006 (www.who.int/malaria/docs/TreatmentGuidelines2006.pdf).
18. Li Q., Weina P.J., and Milhous W.K. Curr. Drug Ther. 2 (2007) 210
19. Lelievre J., Berry A., and Benoit-Vical F. Curr. Opin. Invest. Drugs 8 (2007) 117
20. Golenser J., Waknine J.H., Krugliak M., Hunt N.H., and Grau G.E. Int. J. Parasitol. 36 (2006) 1427
21. Stockwin L.H., Han B., Yu S.X., Hollingshead M.G., ElSohly M.A., Gul W., Slade D., Galal A.M., and Newton D.L. Int. J. Cancer 125 (2009) 1266
22. Maude R.J., Pontavornpinyo W., Saralamba S., Aguas R., Yeung S., Dondorp A.M., Day N.P.J., White N.J., and White L.J. Malar. J. 8 (2009)
23. Noedl H., Se Y., Schaecher K., Smith B.L., Socheat D., and Fukuda M.M. N. Eng. J. Med. 359 (2008) 2619
24. Chadwick J., Mercer A.E., Park B.K., Cosstick R., and O'Neill P.M. Bioorg. Med. Chem. 17 (2009) 1325
25. Galal A.M., Gul W., Slade D., Ross S.A., Feng S., Hollingshead M.G., Alley M.C., Kaur G., and ElSohly M.A. Bioorg. Med. Chem. 17 (2009) 741
26. Posner G.H., D'Angelo J., O'Neill P.M., and Mercer A. Expert Opin. Ther. Patents 16 (2006) 1665
27. Holley Pharmaceutical Company, 1440 N. Harbor Blvd., # 900, Fullerton, CA 92835, USA (www.holleypharma.com).
28. Lin A.J., Klayman D.L., and Milhous W.K. J. Med. Chem. 30 (1987) 2147
29. Lin A.J., Lee M., and Klayman D.L. J. Med. Chem. 32 (1989) 1249
30. ElSohly, M. A.; Gul, W. WO2006002105A1, US20080275106A1, 2006.
31. Grellepois F., Crousse B., Bonnet-Delpon D., and Begue J.-P. Org. Lett. 7 (2005) 5219
32. Jain M., Khan S.I., Tekwani B.L., Jacob M.R., Singh S., Singh P.P., and Jain R. Bioorg. Med. Chem. 13 (2005) 4458
33. Bharate S.B., Khan S.I., Tekwani B.L., Jacob M., Khan I.A., and Singh I.P. Bioorg. Med. Chem. 16 (2008) 1328
34. Mustafa J., Khan S.I., Ma G., Walker L.A., and Khan I.A. Lipids 39 (2004) 167
35. Vonthron-Senecheau C., Weniger B., Ouattara M., Bi Fezan T., Kamenan A., Lobstein A., Brun R., and Anton R. J. Ethnopharmacol. 87 (2003) 221
36. Singh I.P., Lal U.R., Bodiwala H.S., Mahajan R.C., and Bhutani K.K. Recent Prog. Med. Plants 13 (2006) 115
37. Maltezou H.C. Recent Patents Anti Infect. Drug Disc. 3 (2008) 192
38. Sen R., Bandyopadhyay S., Dutta A., Mandal G., Ganguly S., Saha P., and Chatterjee M. J. Med. Microbiol. 56 (2007) 1213
39. Menon R.B., Kannoth M.M., Tekwani B.L., Gut J., Rosenthal P.J., and Avery M.A. Comb. Chem. High Throughput Screening 9 (2006) 729
40. Krishna S., Bustamante L., Haynes R.K., and Staines H.M. Trends Pharmacol. Sci. 29 (2008) 520
41. Wang H., Klinginsmith J., Dong X., Lee A.C., Guha R., Wu Y., Crippen G.M., and Wild D.J. J. Chem. Inf. Model. 47 (2007) 2063
42. Huang R., Wallqvist A., and Covell D.G. J. Med. Chem. 49 (2006) 1964
43. Boyd M.R., and Paull K.D. Drug Dev. Res. 34 (1995) 91
44. Vichai V., and Kirtikara K. Nat. Protocols 1 (2006) 1112
45. Galal A.M., Ross S.A., Jacob M., and ElSohly M.A. J. Nat. Prod. 68 (2005) 1274
46. Lee S. Mini-Rev. Med. Chem. 7 (2007) 411
47. Makler M.T., and Hinrichs D.J. Am. J. Trop. Med. Hyg. 48 (1993) 205
48. Nkhoma S., Molyneux M., and Ward S. Am. J. Trop. Med. Hyg. 76 (2007) 1107
49. Ma G., Khan S.I., Jacob M.R., Tekwani B.L., Li Z., Pasco D.S., Walker L.A., and Khan I.A. Antimicrob. Agents Chemother. 48 (2004) 4450
50. Mikus J., and Steverding D. Parasitol. Int. 48 (2000) 265
51. Hamid R., Rotshteyn Y., Rabadi L., Parikh R., and Bullock P. Toxicol. In Vitro 18 (2004) 703
52. Borenfreund E., Babich H., and Martin-Alguacil N. In Vitro Cell. Dev. Biol.: J. Tissue Culture Assoc. 26 (1990) 1030
53. (a) National Committee for Clinical Laboratory Standards (NCCLS) (Wayne, Pa.): Reference method for broth dilution antifungal susceptibility testing of yeasts; Approved Standard-Second Edition. Document M27-A2, 2002, 22; (b) NCCLS: Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard-Seventh Edition. Document M7-A7, 2006, 26; (c) NCCLS: Susceptibility testing of mycobacteria, nocardia, and other aerobic actinomycetes; Tentative Standard-Approved Standard. Document M24-A, 2003, 23; (d) NCCLS: Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; Approved Standard. Document M38-A, 2002, 22.
54. Franzblau S.G., Witzig R.S., McLaughlin J.C., Torres P., Madico G., Hernandez A., Degnan M.T., Cook M.B., Quenzer V.K., Ferguson R.M., and Gilman R.H. J. Clin. Microbiol. 36 (1998) 362