Natural Products as Anticancer Agents

Natural Products in Chemical Biology

Volumn , Issue , 2012, Pages 325-349

  Kingston, David G I ^a   Newman, David J ^b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Anticancer agents, on DNA or RNA, intercalation, alkylation, or cleavage; Mammalian cell cycle, proteins as anticancer agent targets in cycle control; Natural products as anticancer agents, and new biochemical mechanisms; Natural products as best leads, for novel mechanisms in diseases; Natural products, built in chirality, binding to complex proteins

Indexed keywords

EID: 84886177508     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118391815.ch13     Document Type: Chapter

References (90)

1. Kingston DGI, Newman DJ. The search for novel drug leads for predominately antitumor therapies by utilizing mother nature's pharmacophoric libraries. Curr. Opin. Drug Disc. Develop. 2005;8:207-227.
2. Newman DJ, Cragg GM, Snader KM. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 2003;66:1022-1037.
3. Feher M, Schmidt JM. Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J. Chem. Inf. Comput. Sci. 2003;43:218-227.
4. Ortholand J-Y, Ganesan A. Natural products and combinatorial chemistry: back to the future. Curr. Opin. Chem. Biol. 2004;8:271-280.
5. Butler MS. The role of natural product chemistry in drug discovery. J. Nat. Prod. 2004;67:2141-2153.
6. Clardy J, Walsh C. Lessons from natural molecules. Natur. 2004;432:829-837.
7. Nielsen J. Combinatorial synthesis of natural products. Curr. Opin. Cell. Biol. 2002;6:297-305.
8. Newman DJ, Cragg GM. Natural products as sources of drugs over the last 25 years. J. Nat. Prod. 2007;70:461-477.
9. Noble RL, Beer CT, Cutts JH. Role of chance observation in chemotherapy: Vinca rosea. Ann. N.Y. Acad. Sci. 1958;76:882-894.
10. Neuss N, Cone NJ, Gorman M, Boaz HE. Vinca alkaloids. II. Structures of leurocristine (LCR) and vincaleukoblastine (VLB). J. Am. Chem. Soc. 1962;84: 1509-1510.
11. Svoboda GH. Alkaloids of Vinca rosea (Catharanthus rosea).9. Extraction and characterization of leurosidine and leurocristine. Lloydi. 1961;24:173-178.
12. Joel S. The comparative clinical pharmacology of vincristine and vindesine: Does vindesine offer any advantage in clinical use? Cancer Treat. Rev. 1995;21:513-525.
13. Duflos A, Kruczynski A, Barret J-M. Novel aspects of natural and modified vinca alkaloids. Curr. Med. Chem.: Anti-Cancer Agent. 2002;2:55-70.
14. Gueritte F, Fahy J. The vinca alkaloids. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 123-135.
15. Pettit GR, Cragg GM, Herald DL, Schmidt JM, Lohavanijaya P. Isolation and structure of combretastatin. Can. J. Chem. 1982;60:1374-1376.
16. Pinney KG, Jelinek C, Edvardsen K, Chaplin DJ, Pettit GR. The discovery and development of the combretastatins. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 23-46.
17. Zheng W, Seletsky BM, Palme MH, Lydon PJ, Singer LA, Chase CE, Lemelin CA, Shen Y, Davis H, Tremblay L, et al. Macrocyclic ketone analogues of halichondrin B. Bioorg. Med. Chem. Lett. 2004;14:5551-5554.
18. Jordan MA, Kamath K, Manna T, Okouneva T, Miller HP, Davis C, Littlefield BA, Wilson L. The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth. Mol. Cancer Ther. 2005;4:1086-1095.
19. Dabydeen DA, Burnett JC, Bai R, Verdier-Pinard P, Hickford SJ, Pettit GR, Blunt JW, Munro MHG, Gussio R, Hamel E. Comparison of the activities of the truncated halichondrin B analog NSC 707389 (E7389) with those of the parent compound and a proposed binding site on tubulin. Mol. Pharmacol. 2006;70:1866-1875.
20. Bai R, Pettit GR, Hamel E. Binding of dolastatin-10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. J. Biol. Chem. 1990;265:17141-17149.
21. Cunningham C, Appleman LJ, Kirvan-Visovatti M, Ryan DP, Regan E, Vukelja S, Bonate PL, Ruvuna F, Fram RJ, Jekunen A, et al. Phase I and pharmacokinetic study of the dolastatin-15 analogue tasidotin (ILX651) administered intravenously on days 1, 3, and 5 every 3 weeks in patients with advanced solid tumors. Clin. Cancer Res. 2005;11:7825-7833.
22. Ebbinghaus S, Rubin E, Hersh E, Cranmer LD, Bonate PL, Fram RJ, Jekunen A, Weitman S, Hammond LA. A phase I study of the dolastatin-15 analogue tasidotin (ILX651) administered intravenously daily for 5 consecutive days every 3 weeks in patients with advanced solid tumors. Clin. Cancer Res. 2005;11:7807-7816.
23. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J. Am. Chem. Soc. 1971;93:2325-2327.
24. Gueritte-Voegelein F, Senilh V, David B, Guenard D, Potier P. Chemical studies of 10-deacetyl baccatin III. Hemisynthesis of taxol derivatives. Tetrahedro. 1986;42:4451-4460.
25. Denis J-N, Greene AE, Guenard D, Gueritte-Voegelein F, Mangatal L, Potier P. A highly efficient, practical approach to natural taxol. J. Am. Chem. Soc. 1988;110: 5917-5919.
26. Holton RA, Biediger RJ, Boatman PD. Semisynthesis of taxol and taxotere. In: Taxol: Science and Applications. Suffness M, ed. 1995. CRC Press, Inc., Boca Raton, FL. pp. 97-121.
27. Suffness M, Wall ME. Discovery and development of taxol. In: Taxol: Science and Applications. Suffness M, eds. 1995. CRC Press, Inc., Boca Raton, FL. pp. 3-25.
28. Schiff PB, Fant J, Horwitz SB. Promotion of microtubule assembly in vitro by taxol. Natur. 1979;277:665-667.
29. Piccart MJ, Cardoso F. Progress in systemic therapy for breast cancer: an overview and perspectives. Eur. J. Can. 2003;1 (supp): 56-69.
30. Ozols RF. Progress in ovarian cancer: an overview and perspective. Eur. J. Can. 2003;1 (supp): 43-55.
31. Davies AM, Lara PN, Mack PC, Gandara DR. Docetaxel in non-small cell lung cancer: a review. Exp. Opin. Pharmacother. 2003;4:553-565.
32. Kamath KR, Barry JJ, Miller KM. The taxus drug-eluting stent: a new paradigm in controlled drug delivery. Adv. Drug Deliv. Rev. 2006;58:412-436.
33. Kingston DGI, Newman DJ. Taxoids: cancer-fighting compounds from nature. Curr. Opin. Drug Disc. Dev. 2007;10:130-144.
34. Gradishar WJ. Albumin-bound paclitaxel: a next-generation taxane. Exp. Opin. Pharmacother. 2006;7:1041-1053.
35. Lowe J, Li H, Downing KH, Nogales E. Refined structure of α β-tubulin at 3.5 resolution. J. Mol. Biol. 2001;313:1045-1057.
36. Paik Y, Yang C, Metaferia B, Tang S, Bane S, Ravindra R, Shanker N, Alcaraz AA, Johnson SA, Schaefer J, et al. REDOR NMR distance measurements for the tubulin-bound paclitaxel conformation. J. Am. Chem. Soc. 2007;129:361-370.
37. Ganesh T, Guza RC, Bane S, Ravindra R, Shanker N, Lakdawala AS, Snyder JP, Kingston DGI. The bioactive taxol conformation of β-tubulin: Experimental evidence from highly active constrained analogs. Proc. Natl. Acad. Sci. U.S.A. 2004; 101:10006-10011.
38. Hofle G, Bedorf N, Steinmetz H, Schomburg D, Gerth K, Reichenbach H. Epothilone A and B-novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure, and conformation in solution. Angew Chem Int. Ed. 1996;35:1567-1569.
39. Bollag DM, McQueney PA, Zhu J, Hensens O, Koupal L, Liesch J, Goetz M, Lazarides E, Woods CM. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 1995;55:2325-2333.
40. Giannakakou P, Gussio R, Nogales E, Downing KH, Zaharevitz D, Bollbuck B, Poy G, Sackett D, Nicolaou KC, Fojo T. A common pharmacophore for epothilone and taxanes: Molecular basis for drug resistance conferred by tubulin mutations in human cancer cells. Proc. Natl. Acad. Sci. U.S.A. 2000;97:2904-2909.
41. Frykman S, Tsuruta H, Lau J, Regentin R, Ou S, Reeves C, Carney J, Santi D, Licari P. Modulation of epothilone analog production through media design. J. Ind. Microbiol. Biotech. 2002;28:17-20.
42. Klar U, Buchmann B, Schwede W, Skuballa W, Hoffmann J, Lichtner RB. Total synthesis and antitumor activity of ZK-EPO: the first fully synthetic epothilone in clinical development. Angew Chem Int. Ed. 2006;45:7942-7948.
43. Wu K-D, Cho YS, Katz J, Ponomarev V, Chen-Kiang S, Danishefsky SJ, Moore MAS. Investigation of antitumor effects of synthetic epothilone analogs in human myeloma models in vitro and in vivo. Proc. Natl. Acad. Sci. U.S.A. 2005;102:10640-10645.
44. de Jonge M, Verweij J. The epothilone dilemma. J. Clin. Oncol. 2005;23:9048-9050.
45. Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA. Plant antitumor agents. 1. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. 1966;88:3888-3890.
46. Hsiang YH, Hertzberg R, Hecht S, Liu LF. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol. Chem. 1985;260:14873-14878.
47. Pommier Y. Topoisomerase I inhibitors: camptothecins and beyond. Nat. Rev. Cance. 2006;6:789-802.
48. Rahier NJ, Thomas CJ, Hecht SM. Camptothecin and its analogs. Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 5-21.
49. Sanchez C, Mendez C, Salas JA. Indolocarbazole natural products: occurrence, biosynthesis, and biological activity. Nat. Prod. Rep. 2006;23:1007-1045.
50. Saulnier MG, Balasubramanian BN, Long BH, Frennesson DB, Ruediger E, Zimmerman K, Eummer JT, St. Laurent DR, Stoffan KM, Naidu BN, et al. Discovery of a fluoroindolo[2,3-a]carbazole clinical candidate with broad spectrum antitumor activity in preclinical tumor models superior to the marketed oncology drug, CPT-11. J. Med. Chem. 2005;48:2258-2261.
51. Routier S, Merour J-Y, Dias N, Lansiaux A, Bailly, C, Lozach, O, Meijer, L. Synthesis and biological evaluation of novel phenylcarbazoles as potential anticancer agents. J. Med. Chem. 2006;49:789-799.
52. Hartwell JL, Schrecker AW. Components of podophyllin. V. The constitution of podophyllotoxin. J. Am. Chem. Soc. 1951;73:2909-2916.
53. Lee K-H, Xiao Z. Podophyllotoxin and analogs. 832: In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 71-87.
54. Arcamone F. Anthracyclines. In: Anticancer agents from natural products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 299-320.
55. Zunino F, Capranico G. DNA topoisomerase II as the primary target of anti-cancer anthracyclines. Anticancer Drug Des. 1990;5:307-317.
56. Frederick CA, Williams LD, Ughetto G, Van der Marel GA, Van Boom JH, Rich A, Wang AHJ. Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin. Biochemistr. 1990;29:2538-2549.
57. Isaacs JS. Heat-shock protein 90 inhibitors in antineoplastic therapy: is it all wrapped up? Exp. Opin. Investig. Drug. 2005;14:569-589.
58. Janin YL. Heat shock protein 90 inhibitors. A text book example of medicinal chemistry J. Med. Chem. 2005;48:7503-7512.
59. Chiosis G. Targeting chaperones in transformed systems-a focus on hsp90 and cancer. Exp. Opin. Ther. Targ. 2006;10:37-50.
60. Prudhomme M. Staurosporines and structurally related indolocarbazoles as antitumor agents. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 499-517.
61. Sanchez C, Mendez C, Salas JA. Indolocarbazole natural products: Occurrence, biosynthesis, and biological activity. Nat. Prod. Rep. 2006;23:1007-1045.
62. Feling RH, Buchanan GO, Mincer TJ, Kauffman CA, Jensen PR, Fenical W. Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora. Angew Chem. Int. Ed. 2003;42:355-357.
63. Corey EJ, Li WD. Total synthesis and biological activity of lactacystin, omuralide and analogs. Chem. Pharm. Bull. 1999;47:1-10.
64. Corey EJ, Li WD, Nagamitsu T, Fenteany G. The structural requirements for inhibition of proteasome function by the lactacystin-derived β-lactone and synthetic analogs. Tetrahedro. 1999;55:3305-3316.
65. Reddy LR, Saravanan P, Corey EJ. A simple stereocontrolled synthesis of salinosporamide A. J. Am. Chem. Soc. 2004;126:6230-6231.
66. Reddy LR, Fournier J-F, Reddy BVS, Corey EJ. New synthetic route for the enantioselective total synthesis of salinosporamide A and biologically active analogues. Org. Lett. 2005;7:2699-2701.
67. Mauger AM, Lackner H. The actinomycins. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 281-297.
68. Kawamata J, Imanishi M. Interactions of actinomycin with deoxyribonucleic acid. Natur. 1960;187:1112-1113.
69. Kersten W, Kersten H, Rauen HM. Action of nucleic acids on the inhibition of growth by actinomycin of Neurospora crassa. Natur. 1960;187:60-61.
70. Gniazdowski M, Denny WA, Nelson SM, Czyz M. Transcription factors as targets for DNA-interacting drugs. Curr. Med. Chem.: Anti-Cancer Agent. 2003;10:909-924.
71. Galm U, Hager MH, Van Lanen SG, Ju J, Thorson JS, Shen B. Antitumor antibiotics: bleomycin, enediynes, and mitomycin. Chem. Rev. 2005;105:739-758.
72. Hecht SM. Bleomycin group antitumor agents. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 357-381.
73. Tao Z-F, Konishi K, Keith G, Hecht SM. An efficient mammalian transfer RNA target for bleomycin. J. Am. Chem. Soc. 2006;128:14806-14807.
74. Kumar SG, Lipman R, Cummings J, Tomasz M. Mitomycin c-DNA adducts generated by dt-diaphorase. Revised mechanism of the enzymatic reductive activation of mitomycin C. Biochemistr. 1997;36:14128-14136.
75. Remers WA. The mitomycins. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 475-497.
76. Lee MD, Dunne TS, Siegel MM, Chang CC, Morton GO, Borders DB. Calichemicins, a novel family of antitumor antibiotics. 1. Chemistry and partial structure of calichemicin ? J. Am. Chem. Soc. 1987;109:3464-3466.
77. Lee MD, Dunne TS, Chang CC, Ellestad GA, Siegel MM, Morton GO, McGahren WJ, Borders DB. Calichemicins, a novel family of antitumor antibiotics. 2. Chemistry and structure of calichemicin ? J. Am. Chem. Soc. 1987;109:3466-3468.
78. Golik J, Clardy J, Dubay G, Groenewold G, Kawaguchi H, Konishi M, Krishnan B, Ohkuma H, Saitoh K, Doyle TW. Esperamicins, a novel class of potent antitumor antibiotics. 2. Structure of esperamicin X. J. Am. Chem. Soc. 1987;109: 3461-3462.
79. Golik J, Dubay G, Groenewold G, Kawaguchi H, Konishi M, Krishnan B, Ohkuma H, Saitoh K, Doyle TW. Esperamicins, a novel class of potent antitumor antibiotics. 3. Structures of esperamicins A1, A2, and A1b. J. Am. Chem. Soc. 1987;109: 3462-3464.
80. Hamann PR, Upeslacis J, Borders DB. Enediynes. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, eds. 2005. Taylor and Francis, Boca Raton, FL. pp. 451-474.
81. Rinehart KL, Holt TG, Fregeau NL, Stroh JG, Keifer PA, Sun F, Li LH, Martin DG. Ecteinascidins 729, 743, 745, 759a, 759b, and 770: potent antitumor agents from the caribbean tunicate Ecteinascidia turbinata. J. Org. Chem. 1990;55:4512-4515.
82. Wright AE, Forleo DA, Gunawardana GP, Gunasekera SP, Koehn FE, McConnell OJ. Antitumor tetrahydroisoquinoline alkaloids from the colonial ascidian Ecteinascidia turbinata. J. Org. Chem. 1990;55:4508-4512.
83. Cuevas C, Perez M, Martin M, Chicharro JL, Fernandez-Rivas C, Flores M, Francesch A, Gallefo P, Zarzuelo M, de la Calle F, et al. Synthesis of ecteinascidin ET-743 and phthalascidin PT-650 from cyanosafracin B. Org. Lett. 2000;2:2545-2548.
84. Fayette J, Coquard IR, Alberti L, Ranchere D, Boyle H, Blay J-Y. ET-743: a novel agent with activity in soft tissue sarcomas. Oncologis. 2005;10:827-832.
85. Lynch GR, Lane M. Other antitumor antibiotics. In: Cancer Management in Man. Woolley PV, ed. 1989. Kluwer Academic Publishers, Dordrecht. pp. 134-146.
86. Koschmieder S, Agrawal S, Radomska HS, Huettner CS, Tenen DG, Ottmann OG, Berdel WE, Serve HL, Muller-Tidow C. Decitabine and vitamin D3 differentially affect hematopoietic transcription factors to induce monocytic differentiation. Int. Oncol. 2007;30:349-355.
87. Dolan ME. Inhibition of DNA repair as a means of increasing the antitumor activity of DNA reactive agents. Adv. Drug Deliv. Rev. 1997;26:105-118.
88. Arnold R, Rinke A, Schmidt C, Hofbauer L. Chemotherapy. Best Pract. Res. Clin. Gastroent. 2005;19:649-656.
89. Wilhelm S, Carter C, Lynch M, Lowinger T, Dumas J, Smith RA, Schwartz B, Simantov R, Kelley S. Discovery and development of sorafenib: a multikinase inhibitor for treating cancer. Nature Rev. Drug Discov. 2006;5:835-844.
90. Cragg GM, Kingston DGI, Newman DJ, eds. Anticancer Agents from Natural Products. 2005. CRC Press; Boca Raton, FL.