Calanolides, the naturally occurring anti-HIV agents

Current Opinion in Drug Discovery and Development

Volumn 3, Issue 2, 2000, Pages 155-166

  Xu, Ze Qi ^a   Flavin, Michael T ^a   Jenta, Tuah R ^a  

^a MediChem Research Inc   (United States)

Author keywords

(+) Calanolide A; Calanolides; HIV; Natural products; NNRTI; Resistance

Indexed keywords

ABACAVIR; AMPRENAVIR; CALANOLIDE A; DELAVIRDINE; DIDANOSINE; EFAVIRENZ; INDINAVIR; LAMIVUDINE; NELFINAVIR; NEVIRAPINE; RITONAVIR; RNA DIRECTED DNA POLYMERASE INHIBITOR; SAQUINAVIR; STAVUDINE; ZALCITABINE; ZIDOVUDINE;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENTIATION; DRUG SAFETY; DRUG STRUCTURE; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0033994765     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (42)

1. AIDS Research -1998. Science (1998) 280:1865-1894. Several review articles outlining the recent progress and challenges of AIDS research.
2. Vaishnav YN, Wong-Staal F The biochemistry of AIDS. Ann Rev Biochem (1991) 60:577-630.
3. Arnold E, Arnold GF Human immunodeficiency virus structure: Implications for antiviral design. Adv Virus Res (1991)39:1-87.
4. Goff SP Retroviral reverse transcriptase: synthesis, structure, and function. JAIDS (1990) 3:817-831.
5. Jacobo-Molina A, Arnold E HIV reverse transcriptase structure-function relationships. Biochemistry (1991) 30:6351-6356.
6. Thaisrivongs S HIV protease Inhibitors. In: Annual Reports in Medicinal Chemistry. Bristol JA (Ed), Academic Press (1994) 29:133-144.
7. Chun T-W, Davey RT Jr, Engel D, Lane HC, Fauci SF Reemergence of HIV after stopping therapy. Nature (1999) 401:874-875.
8. Kashman Y, Gustafson KR, Fuller RW, Cardellina JH, McMahon JB, Currens MJ, Buckheit RW, Hughes SH, Cragg GM, Boyd MR The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J Med Chem (1992) 35:2735-2743.
9. McKee TC, Covington, CD, Fuller RW, Bokesch HR, Young S, Cardellina JH, Kadushin MR, Soejarto DD, Stevens PF, Cragg GM, Boyd MR Pyranocoumarins from tropical species of the genus Calophyllum: A chemotaxonomic study of extracts in the National Cancer Institute collection. J Nat Prod (1998) 61:1252-1256.
10. Boyer PL, Currens MJ, McMahon JB, Boyd MR, Hughes SH Analysis of nonnucleoside drug-resistant variants of human immunodeficiency virus type 1 reverse transcriptase. J Virol (1993) 67:2412-2420.
11. Hizi A, Tal R, Shaharabany M, Currens MJ, Boyd MR, Hughes SH, McMahon JB Specific inhibition of the reverse transcriptase of human immunodeficiency virus type 1 and the chimeric enzymes of human immunodeficiency virus type 1 and type 2 by nonnucleoside inhibitors. Antimicrob Agents Chemother (1993) 37:1037-1042.
12. Buckheit RW Jr, Fiiakas-Boltz V, Decker WD, Roberson JL, Stup TL, Pyie CA, White EL, McMahon JB, Currens MJ, Boyd MR, Bader JP Comparative anti-HIV evaluation of diverse HIV-1-specific reverse transcriptase inhibitor-resistant virus isolates demonstrates the existence of distinct phenotypic subgroups. Antiviral Res (1995) 26:117-132.
13. Sorbera LA, Leeson P, Castaner J Calanolide A. Drugs Future (1999) 24:235-245.
14. Khilevich A, Mar A, Flavin MT, Rizzo JD, Dzekhtser S, Brankovic D, Lin L, Zhang H, Chen W, Liao S, Zembower DE, Xu Z-Q Synthesis of (+}-calanolide A, an anti-HIV agent, via enzyme-catalyzed resolution of the aldol products. Tetrahedron Asymmetry (1996) 7:3315-3326.
15. Flavin MT, Rizzo JD, Khilevich A, Kucherenko A, Sheinkman AK, Vilaychack V, Lin L, Chen W, Greenwood ME, Pengsuparp T, Pezzuto JM, Hughes SH, Flavin TM, Cibulski M, Boulanger WA, Shone RL, Xu Z-Q Synthesis, Chromatographie resolution and anti-HIV activity of (±)-calanolide A and its enantiomers. J Med Chem (1996) 39:1303-1313.
16. Currens MJ, Gulakowski RJ, Mariner JM, Moran RA, Buckheit RW Jr, Guslafson KR, McMahon JB, Boyd MR Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus type-1. J Pharmacol Exp Trier (1996) 279:645-651.
17. Buckheit RW Jr, White EL, Fliakas-Boltz V, Russell J, Stup TL, Kinjerski TL, Ostering MC, Weigand A, Bader JP Unique antihuman immunodeficiency virus activities of the nonnucteoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob Agents Chemother (1999) 43:1827-1834.
18. Currens MJ, Mariner JM, McMahon JB, Boyd MR Kinetic analysis of inhibition of human immunodeficiency virus type-1 reverse transcriptase by calanolide A. J Pharmacol Exp T/7er(1996) 279:652-661.
19. Arnold E, Das K, Ding J, Yadav PN, Hsiou Y, Boyer PL, Hughes SH Targeting H1V reverse transcriptase for antiAIDS drug design: structural and biological considerations for chemotherapeutic strategies. Drug Des Discov (1996) 13:29-47.
20. Ding J, Das K, Hsiou Y, Zhang W, Arnold E, Yadav PN, Hughes SH Structural studies of HIV-1 reverse transcriptase and implications for drug design. In: Structure-based Drug Design. Veerapandian P (Ed), Marcel Dekker, New York (1997):Chapter 2, 41-82.
21. Quan Y, Motakis D, Buckheit RW Jr, Xu Z-Q, Flavin MT, Parniak MA, Wainberg MA Sensitivity and resistance of (+}calanolide A of wild-type and mutated forms of HIV-1 reverse transcriptase. Antiviral Therapy (1999) 4:203-209.
22. Xu Z-Q, Hertogs K, Van den Eynde C, Bloor S, Larder B, Dutta B In vitro phenotypic resistance profile of (+)-calanolide A, a naturally occurring NNRTI, against clinical Isolates of HIV-1 with Y181C mutation. ICAAC(W99) 39:440.
23. Buckheit RW Jr, Russell J, Boltz VF, Pallansch LA, Xu Z-Q, Flavin MT: Combination anti-HIV interactions and resistance profile of the nonnucleoside RT inhibitor (+)calanolide A. 12th World AIDS Conference, Geneva, Switzerland (1998):12366.
24. Xu Z-Q, Hollingshead MG, Borgel S, Elder C, Khilevich A, Ravin MT In vivo anti-HIV activity of (+}-calanolide A in the hollow fiber mouse model. Bioorg Med Chem Lett (1999) 9:133-138.
25. Frank P, Flavin MT, Roca-Actin J, Xu Z-Q: Safety assessment of (+)-calanolide A, a naturally occurring anti-HIV agent. Fourth Conference on Retroviruses and Opportunistic Infections, Washington, DC, USA (1997):225.
26. Cardellina JH, II, Bokesch HR, McKee TC, Boyd MR Resolution and comparative anti-HIV evaluation of the enantiomers of calanolides A and B. Bioorg Med Chem Lett (1995)5:1011-1014.
27. Fuller RW, Bokesch HR, Gustafson KR, McKee TC, Cardellina JH, McMahon JB, Cragg GM, Soejarto DD, Boyd MR HIVinhibitory coumarins from latex of the tropical rainforest tree Calophyllum teysmannii var inophylloide. Bioorg Med Chem ieff(1994) 4:1961-1964.
28. Spino C, Dodier M, Sotheeswaran S Anti-HIV coumarins from Calophyllum seed oil. Bioorg Med Chem Lett (1998) 8:3475-3478.
29. Lin Y-M, Anderson HM, Jenta TR, Williams MJ, Flavin MT, Xu Z-Q: An efficient and scaleable method for the isolation of costatolide, a naturally-occurring anti-HIV ayent, from the latex of Calophyllum teysmannii var inophylloide. Pharm Biol (1999) 37:71 -76.
30. Deshapande PP, Tagliaferri F, Victory SF, Yan S, Baker DC Synthesis of optically active calanolide A and B. J Org Chem (1995) 60:2964-2965.
31. Soejarto DD, Ismawi O, Kadushin MR, Lee HS: Sustainable harvest of latex containing anti-HIV compound from Calophullym teysmannii var inophyllolde. 38th Annual Meeting of the American Society of Pharmacognosy, The University of Iowa, USA (1997):P94.
32. Galinis DL, Fuller RW, McKee TC, Cardellina JH, Gulakowski RJ, McMahon JB, Boyd MR Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-}-calanolide B. J Med Chem (1996) 39:4507-4510.
33. Pali! AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF, Taylor PB, Caranfa MJ, Breen All, Bartus HR, Johnson RK, Hertzberg RP, Westley JW The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum Inophyllum Linn. J Med Chem (1993)36:4131-4138.
34. Taylor PB, Gulp JS, Debouck C, Johnson RK, Paul AD, Woolf DJ, Brooks l, Hertzberg RP Kinetic and mutational analysis of human immunodeficiency virus type 1 reverse transcriptase inhibition by inophyllums, a novel class of non-nucleoside inhibitors. JBiol Chem (1994) 269:6325-6331.
35. Xu Z-Q, Buckheit RW Jr, Stup TL, Ravin MT, Khilevich A, Rizzo JD, Lin L, Zembower DE In vitro anti-human immunodeficiency virus (HIV) activity of the chromanone derivative, 12-oxocalanolide A. A novel NNRTI. Bioorg Med Chem Lett (1998) 8:2179-2184.
36. Xu Z-Q, Kern ER, Westbrook L, Allen LB, Buckheit RW Jr, Tseng CK, Ravin MT Plant-derived and semisynthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus. Antiviral Chem Chemother(200Q) 11:23-29.
37. Zembower DE, Liao S, Flavin MT, Xu Z-Q, Stup TL, Buckheit RW Jr, Khilevich A, Mar AA, Sheinkman AK Structural analogues of the calanolide anti-HIV agents. Modification of the rrans-10,11-dimethyldihydropyran-12-ol ring (ring C). JMed Chem (1997) 40:1005-1017.
38. Gustafson KR, Bokesch HR, Fuller RW, Cardellina JH, Kadushin MR, Soejarto DD, Boyd MR Calanone, a novel coumarin from Calophyllum teysmannii. Tetrahedron Lett (1994)35:5821-5824.
39. Gunasekera SP, Jayatilake GS, Sciliah SS, Sultanbawa MUS Chemical investigation of Ceylonese plants. Part 27. Extractives of Calophyllum cuneifolium Thw and Calophyllum soulattrl Burm f (Guttiferae). J Chem See Perkin Trans 1 (1977):1505-1511.
40. Dharmaratne HR, Wanigasekera, WM, Mata-Greenwood E, Pezzuto JM Inhibition of human immunodeficiency virus type 1 reverse transcriptase activity by cordatolides isolated from Calophyllum cordato-oblongum. Planta Med (1998)64:460-461.
41. Zembower DE, Chandrasekar P, Liao S, Xu Z-Q, Ravin MT High speed analogue synthesis. Derivatives of calanolide A, an anti-HIV agent, via solution phase combinatorial synthesis. 21ST National Meeting of the American Chemical Society, San Francisco, USA (1997):MEDI-111.
42. Ding J, Das K, Moereeis H, Koymans L, Andries K, Janssen PA, Hughes SH, Arnold E Structure of HIV-1 RT/T1BO R 86183 reveals similarity in the binding of diverse nonnucleoside inhibitors. NatureStruct B/b/(1995) 2:407-415.