Natural products based anticancer agents

Mini-Reviews in Organic Chemistry

Volumn 9, Issue 2, 2012, Pages 169-177

  Das, Biswanath ^a   Satyalakshmi, Gandham ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Anticancer compounds; Bioactivities; Commercial drugs; Mode of action; Natural products; Sources; Structure activity relationship

Indexed keywords

EID: 84861141370     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019312800604706     Document Type: Article

References (137)

1. Danaei, G.; Horn, S. V.; Lopez, A. D.; Murray, C. J. L.; Ezzati, M. Causes of cancer in the world: Comparative risk assessment of nine behavioural and environmental risk factors. The Lancet 2005, 366, 1784-1793.
2. Hartwell, J. L. Plants used against cancer. A survey. Lloydia 1969, 32, 153-205.
3. Newman, D. J.; Cragg, G. M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007, 70, 461-477.
4. Nicolaou, K. C.; Chen, J. S.; Dalley, S. M. From nature to the laboratory and into the clinic. Bioorg. Med. Chem. 2009, 17, 2290-2303.
5. Mohammad, S. Anticancer agents from medicinal plants. Bangladesh J. Pharmacol. 2006, 1, 35-41.
6. Altmann, K-H.; Gertsch, J. Anticancer agents from nature - Natural products as a unique source of new microtubulestabilizing agents. Nat. Prod. Res. 2007, 24, 327-357.
7. Gordaliza, M. Natural products as leads to anticancer drugs. Clin. Transl. Oncol. 2007, 9, 767-776.
8. Kingston, D. G. I. Tubulin-interactive natural products as anticancer agents. J. Nat. Prod. 2009, 72, 507-515.
9. Dewar, M. J. S. Structure of colchicine. Nature 1945, 155, 141-142.
10. King, M. V.; Devies, J. L.; Pepinsky, R. An X-ray diffraction determination of the chemical structure of colchicine. Acta Cryst 1952, 5, 437-440.
11. Hartwell, J. L.; Schrecker, A. W. Components of podophyllin. V. The constitution of podophyllotoxin. J. Am. Chem. Soc 1951, 73, 2909-2916.
12. Hartwell, J. L.; Schrecker, A. W. Chemistry of podophyllum. Fortschr. Chem. Org. Naturstoffe 1958, 15, 83-166.
13. Chang, F. C.; Chaig, C. K.; Alyar, V. N. Isopicropodophyllone from Podophyllum pleianthum. Phytochemistry 1975, 14, 1440.
14. Jackson, D. E.; Dewick, P. M. Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum. Phytochemistry 1984, 23, 1147-1152.
15. Noble, R. L.; Beer, C. T.; Cutts, J. H. Role of chance observations in chemotherapy: Vinca rosea. Ann. N. Y. Acad. Sci. 1958, 76, 882-894.
16. Svoboda, G. H. A note on several new alkaloids from Vinca rosea Linn. I: Leurosine, virosine, perivine. J. Pharm. Sci. 1958, 47, 834.
17. Svoboda, G. H.; Johnson, I. S.; Gorman, M., Neuss, N. Current status of research on the alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don). J. Pharm. Sci. 1962, 51, 707-720.
18. Goodwin, S.; Smith, A. F.; Horning, E. C. Alkaloids of Ochrosia elliptica Labill. J. Am. Chem. Soc. 1959, 81, 1903-1908.
19. Neuss, N. In: Indole and biogenetically related alkaloids, (Eds. Phillipson, J. D.; Zenk, M. H), Academic Press, London, 306-309.
20. Herz, W.; Watanabe, H.; Miyazaki, M.; Kishida, Y. The structures of parthenin and ambrosin. J. Am. Chem. Soc 1962, 84, 2601-2610.
21. Kupchan, S. M.; Eakin, M. A.; Thomos, A. M. Tumor inhibitors. 69. Structurecytotoxicity relations among the sesquiterpene lactones. J. Med. Chem. 1971, 14, 1147-1152.
22. Carboni, S.; Malaguzzi, V.; Marsili, A. Ferulenol a new coumarin derivative from ferula communis. Tetrahedron Lett. 1964, 5, 2783-2786.
23. Wall, E.; Wani, M. C.; Cook, C. E.; Palmar, K. H.; McPhail, A. T.; Sui, G. A. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. 1966, 88, 3888-3890.
24. Govindachari, T. R.; Viswanathan, N. 9-Methoxycamptothecin. A new alkaloid from Mappia foetida Miers. Indian J. Chem. 1972, 16, 453-454.
25. Roja, G.; Heble, M. R. The quinoline alkaloids camptothecin and 9-methoxycamptothecin from tissue cultures and mature trees of Nothapodytes foetida. Phytochemistry 1994, 36, 65-66.
26. Kupchan, S. M.; Sigel, C. N.; Matz, M. J.; Renauld, J. A. S.; Haltiwagner, R. C.; Bryan, R. F. Jatrophone, a novel macrocyclic diterpenoid tumor inhibitor from Jatropha gossypiifolia. J. Am. Chem. Soc. 1970, 92, 4476-4477.
27. Kupchan, S. M.; Sigel, C. N.; Matz, M. J.; Gilmore, C. J.; Bryan, R. F. Tumor inhibitors. 111. Structure and stereochemistry of jatrophone, a novel macrocyclic diterpenoid tumor inhibitor. J. Am. Chem. Soc. 1976, 98, 2295-2300.
28. Das, B.; Ravikanth, B.; Reddy, K. R.; Thirupathi, P.; Raju, T. V. Sridhar, B. Diterpenoids from Jatropha multifida. Phytochemistry 2008, 69, 2639-2641.
29. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggor, P.; McPhail, A. T. Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J. Am. Chem. Soc. 1971, 93, 2325-2327.
30. Kingston, D. G. I. The chemistry of taxol. Pharm. Ther. 1992, 52, 1-34.
31. Senilh, V.; Blechert, S.; Colin, M.; Guenard, D.; Picot, F.; Varenne, P. Mise en evidence de nouveaux analogues du taxol extraits de Taxus baccata. J. Nat. Prod. 1984, 47, 131-137.
32. Das, B.; Kashinatham, A. New phytoconstituents of yew plants. J. Sci. Ind. Res. 1996, 55, 246-258.
33. Quinoa, E.; Xakou, Y.; Crews, P. Fijianolides, polyketide heterocycles from a marine sponge. J. Org. Chem. 1988, 53, 3642-3644.
34. Corley, D. G.; Herb, R.; Moore, R. E.; Schever, P. Laulimalides. New potent cytotoxic macrolides from a marine sponge and a nudibranch predator. J. Org. Chem. 1988, 53, 3644-3646.
35. Gunasekera, S. P.; Cranick, S.; Longley, R. E. Immunosuppressive compounds from a deep water marine sponge, Agelas flabelliformis. J. Nat. Prod. 1989, 52, 757-761.
36. Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. Dynemicin A, a novel atibiotic with the anthraquinone and 1, 5-diyn-3-ene subunit. J. Antibiot. 1989, 42, 1449-1452.
37. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. Crystal and molecular structure of dynemicin A: a novel 1,5-diyn-3-ene antitumor antibiotic. J. Am. Chem. Soc. 1990, 112, 3715-3716.
38. Pettit, G. R.; Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S., Garcia, K. D. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A4. Experentia 1989, 45, 209-211.
39. Hofle, G.; Bedorf, N.; Steinmertz, H.; Schomburg, D.; Gerth, K.; Reichenach, H. Epothilone A and B-novel 16-membered macrolides with cytotoxic activity: isolation, crystal structure, and conformation in solution. Angew. Chem. 1996, 35, 1567-1569.
40. Lindel, T.; Jensen, P. R.; Fenical, W.; Long, B. H.; Casazza, A. M.; Carboni, J. M.; Fairchild, C. R. Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules. J. Am. Chem. Soc. 1997, 119, 8744-8745.
41. ®). Cancer. Res. 1998, 58, 1111-1115.
42. Manzo, E.; Van Soest, R.; Matainaho, L.; Roberge, M.; Andersen, R. J. Ceratamines A and B, antimitotic heterocyclic alkaloids isolated from the marine sponge Pseudoceratina sp. collected in Papua New Guinea. Org. Lett. 2003, 5, 4591-4594.
43. Harish, H.; Srinivas, Y.; Majhi, A.; Srinivasulu, G.; Sridhar, B.; Krishna, A. S.; Rao, J. V.; Das, B. Novel cytotoxic constituents of Orthosiphon diffusus. Tetrahedron Lett. 2011, 52, 49-52.
44. Gordaliza, M.; Garcia, P. A.; Miguel del Corral, J. M.; Castro, M. A.; Gomez- Zurita, M. A. Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Toxicon 2004, 44, 441-459.
45. Imbert, T. M. Discovery of podophyllotoxins. Biochieme 1998, 80, 207-222.
46. Gordaliza, M.; Castro, M. A.; Miguel del Corral, J. M.; San Feliciano, A. Antitumor properties of podophyllotoxin and related compounds. Curr. Pharm. Des. 2000, 6, 1811-1839.
47. Utsugi, T.; Shibata, J.; Sugimoto, Y.; Aoyagi, K.; Wierzba, K.; Kobunai, T.; Terada, T.; Oh-hara, T.; Tsuruo, T.; Yamada, Y. Antitumor activity of a novel podophyllotoxin derivative (TOP-53) against lung cancer and lung metastatic cancer. Cancer. Res. 1996, 56, 2809-2814.
48. Subramanyam, D.; Renuka, B.; Rao, C. B.; Sagar, P. S.; Deevi, D. S.; Babu, J. M.; Vyas, K. Novel D-ring analogues of podophyllotoxin as potent anti-cancer agents. Bioorg. Med. Chem. Lett. 1998, 8, 1391-1396.
49. Juslen, C. K.; Kuhn, M.; Von Wartburg, A.; Stahelin, H. Mitosisinhibiting natural products. 24. Synthesis and antimitotic activity of glycosidic lignan derivatives related to podophyllotoxin. J. Med. Chem. 1971, 14, 936-940.
50. Andrews, R. C.; Teague, S. J.; Meyers, A. I. Asymmetric total synthesis of (-)-podophyllotoxin. J. Am. Chem. Soc. 1988, 110, 7854-7858.
51. Zhang, Y. L.; Guo, X.; Cheng, Y. C.; Lee, K. H. Antitumor Agents. 148. Synthesis and biological evaluation of novel 4β-amino derivatives of etoposide with better pharmacological profiles. J. Med. Chem. 1994, 37, 446-452.
52. Cho, S. J.; Kashiwada, Y.; Bastow, K. F.; Cheng, Y. C.; Lee, L. H. Antitumor agents. 164. Podophenazine, 2,3-dichloropodophenazine, benzopodophenazine, and their 4β-p-nitroaniline derivatives as novel DNA Topoisomerase II inhibitors. J. Med. Chem. 1996, 39, 1396-1402.
53. Issel, B. F. The podophyllotoxin derivatives VP16-213 and VM26. Cancer Chemother. Pharmacol. 1982, 1, 73-80.
54. Thruston, L. S.; Irie, H.; Tani, S.; Han, F. S.; Liu, Z. C.; Chem, Y. C.; Lee, K. H. Antitumor agents. 78. Inhibition of human DNA topoisomerase II by podophyllotoxin and α-peltatin analogs. J. Med. Chem. 1986, 29, 1547-1550.
55. Thruston, L. S.; Imakura, Y.; Haruna, M.; Li, D. H.; Liu, Z. C.; Liu, S. Y.; Chemg, Y. C.; Lee, K. H. Antitumor agents. 100. Inhibition of human DNA topoisomerase II by cytotoxic ether and ester derivatives of podophyllotoxin and α-peltatin. J. Med. Chem. 1989, 32, 604-608.
56. Neuss, N.; Gorman, M.; Hargrove, W.; Cone, N. J.; Biemann, K.; Buchi, G.; Marning, R. E. Vinca alkaloids. XXI. The structures of the oncolytic alkaloids vinblastine (VLB) and vincristine (VCR). J. Am. Chem. Soc. 1964, 86, 1440-1442.
57. Moncrief, J. W.; Lipscomb, W. N. Structure of leurocristine methiodide dihydrate by anomalous scattering methods: relation to leurocristine (vincristine) and vincaleukoblastine (vinblastine). Acta Cryst 1966, 21, 322-331.
58. Taylor, G. Introduction to symposium on vincristine. Cancer Chemother. Rep. 1968, 52, 453-535.
59. Cutts, J. H.; Beer, C. T.; Noble, R. L. Biological properties of vincaleukoblastine, an alkaloid in Vinca rosea Linn, with reference to its antitumor action. Cancer Res. 1960, 20, 1023-1031.
60. Zubrod, C. G. In: Antineoplastic and immunesuppressive agents, Ed. Verlag, A. C.; New York, pp 1-11.
61. Henderson, E. S.; Samaha, R. J. Evidence that drugs in multiple combinations have materially advanced the treatment of human malignancies. Cancer Res. 1969, 29, 2272-2280.
62. Palmer, C. G.; Livengood, D.; Warren, A.; Simpson, P. J.; Johnson, I. S. The action of vincaleukoblastine on mitosis in vitro. Exp. Cell Res. 1960, 20, 198-201.
63. Barnett, C. J.; Cullinan, G. J.; Gezzon, K.; Hoying, R. C.; Jones, W. E.; Newton, W. M.; Roore, G. A.; Robinson, R. L.; Sweeney, M. J.; Todd, G. C.; Oyker, R. W.; Nelson, R. L. Structure-activity relationships of dimeric Catharanthus alkaloids. 1. deacetyl vinblastine amide (vindesine) sulfate. J. Med. Chem. 1978, 21, 88-96.
64. 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.
65. Mano, M. Vinorelbine in the management of breast cancer: New perspectives, revived role in the era of targeted therapy. Cancer Treat. Rev. 2006, 32, 106-118.
66. Das, B.; Rao, S. P.; Kashinatham, A.; Srinivas, K. V. S. N. Studies on phytochemicals.15. Investigation on the alkaloidal constituents of Indian Mappia foetida. Indian J. Chem. 1997, 36B, 208-210.
67. McPhail, A. T.; Sim, G. A. The structure of camptothecin: X-ray analysis of camptothecin iodoacetate. J. Chem. Soc. B, 1968, 923-928.
68. Wenkert, E.; Dave, K. G.; Lews, R. G.; Sprague, P. W. General methods of synthesis of indole alkaloids. VI. Syntheses of dl-corynantheidine and a camptothecin model. J. Am. Chem. Soc. 1967, 89, 6741-6745.
69. Das, B.; Anjani, G.; Kashinatham, A. Occurrence of 5-methoxy-1-oxo-tetrahydrobeta-carboline in Indian Nothapodytes foetida - an important clue to the biogenetic formation of camptothecins. Nat. Prod. Lett. 1998, 11, 285-289.
70. Kessel, D. Effects of camptothecin on RNA synthesis in leukemia L1210 cells. Biochem. Biophys. Acta. 1971, 246, 225-232.
71. Hutchinson, C. R. Tetrahedron report number 105: Camptothecin: chemistry, biogenesis and medicinal chemistry. Tetrahedron 1981, 37, 1047-1065.
72. Moertel, C. G.; Schutt, A. J.; Reitemeier, R. J. Phase I1 study of camptothecin (NSC l00880) in the treatment of advanced gastrointestinal cancer. Cancer Chemother. Rep. 1972, 56, 95-101.
73. Hsiang, Y. H.; Hertzberg, R. P.; Hecht, S.; Liu, L. F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol. Chem. 1985, 260, 14873-14878.
74. Hsiang, Y. H.; Liu, L. F. Identification of mammalian DNA Topoisomerase I as an intracellular target of the anticancer drug camptothecin. Cancer Res. 1988, 48, 1722-1726.
75. Fukuda, M. Action of camptothecin and its derivatives on deoxyribonucleic acid. Biochem. Pharmacol. 1985, 34, 1225-1230.
76. Kunimoto, T.; Nitta, K.; Tanaka, T.; Uehara, N.; Baba, H.; Takeuchi, M.; Yokokura, Y.; Sawada, S.; Miyasara, T.; Mutai, M. Antitumor activity of 7- ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin, a novel water-soluble derivative of camptothecin, against murine tumors. Cancer Res. 1987, 47, 5944-5947.
77. Sawada, S.; Okajunia, S.; Aiyama, R.; Nolata, K.; Faruta, T.; Yokokura, Y.; Sigino, E.; Yamanouchi, K.; Miyasaka, T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives: carbamatelinked, water-soluble derivaties of 7-ethyl-10-hydroxycamptothecin. Chem. Pharm. Bull. 1991, 39, 1446-1454.
78. Kingsburry, W. D.; Bohm, J. C.; Jaes, D. R.; Holden, K. G.; Hecht, S. M.; Gallaghar, G.; Caranfa, M. J.; McCabe, F. L.; Faucette, L. F.; Johnson, R. K.; Hertzberg, R. P. Synthesis of water-soluble (aminoalkyl)camptothecin analogs: inhibition of topoisomerase I and antitumor activity. J. Med. Chem. 1991, 34, 98-107.
79. Witherup, K. M.; Look, S. A.; Stasko, M. W.; Ghiorzi, T. J.; Musehik, G. M; Cragg, G. M. Taxus spp. Needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation. J. Nat. Prod. 1990, 62, 1249-1255.
80. Das, B.; Rao, S. P. Naturally occurring oxetane-type taxoids. Indian J. Chem. 1996, 35B, 883-893.
81. Baloglu, E.; Kingston, D. G. I.; The taxane diterpenoids. J. Nat. Prod. 1999, 62, 1448-1472.
82. Millar, R. W.; Powell, R. G.; Smith Jr., C.R.; Arnold, E.; Clardy, J. Antileukemic alkaloids from Taxus wallichiana Zucc. J. Org. Chem. 1981, 46, 1469-1474.
83. Chattopadyay, S. K.; Tripathi, V. K.; Thakur, R. S.; Sharma, R. P. Jain, S. P. Isolation of taxol, 10-deacetyl baccatin III and (-)betuligenol from Taxus baccata. Indian J. Chem. 1994, 33B, 409-411.
84. Rojatkar, S. R.; Sawaikar, D.D.; Simha, B.; Ravindranathan, T.; Nagasampagi, B. A. 4-(phydroxyphenyl)-(2S)-butanol from the needles of Taxus baccata. Phytochemistry 1996, 39, 259-260.
85. Das, B.; Das, R. Taxoids from the Himalayan yew, a potent anticancer plant. Indian J. Pharm. Sci. 1994, 56, 199-204.
86. McGuire, W. P.; Rowinsky, E. K.; Rosenshein, N. B.; Grumbine, F. C.; Ettinger, D. S.; Armstrong, D. K.; Donehower, B. C. Taxol: A unique antineoplastic agent with significant activity in advanced ovarian epithelial neoplasms. Ann. Int. Med. 1989, 111, 273-279.
87. Rownisky, E. K.; Cazenave, L. A.; Donehower, B. C. Taxol: A novel investigational antimicrotubule agent. J. Natl. Cancer. Inst. 1990, 82, 1247-1259.
88. Powinsky, E. K.; Donehower, R. C. Taxol: twenty years later, the story unfolds. J. Natl. Cancer. Inst. 1991, 83, 1778-1781.
89. Schiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of microtubule assembly in vitro by taxol. Nature 1979, 277, 665-667.
90. Parness, J.; Horwitz, S. B. Taxol binds to polymerized tubulin in vitro. J. Cell. Biol. 1981, 91, 479-487.
91. Manfredi, J. J.; Horwitz, S. B. Taxol: an antimitotic agent with a new mechanism of action. Pharm. Ther. 1984, 25, 83-125.
92. Kingston, D. G. I. Taxol: The chemistry and structure-activity relationships of a novel anticancer agent. Trends in Biotech. 1994, 12, 222-227.
93. Bissery, M-C.; Guenard, D.; Gueritte-Voegelein, P.; Lavelle, P. Experimental antitumor activity of taxotere (RP 56976. NSC 628503), a taxol analogue Cancer Res. 1991, 51, 4845-4852.
94. Guenard, D.; Gueritte-Voegelein, P.; Potier, P. Taxol and taxotere: discovery, chemistry, and structure-activity relationships. Acc. Chem. Res. 1993, 26, 160-167.
95. Nicolaou, K. C.; Reimer, C.; Kerr, M. A.; Rideout, D.; Wrasidlo, W. Design, synthesis and biological activity of protaxols. Nature 1993, 364, 464-466.
96. Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. B.; Shimoda, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Va, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. First total synthesis of taxol. 1. Functionalization of the B ring. J. Am. Chem. Soc. 1994, 116, 1597-1598.
97. Holton, R. A.; Kim, H. B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. B.; Shindo, M.; Smith, C. C.; Kim, S. First total synthesis of taxol. 2. completion of the C and D rings. J. Am. Chem. Soc. 1994, 116, 1599-1600.
98. Nocolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Total synthesis of taxol. Nature 1994, 360, 630-634.
99. Fett-Neto, A. G.; Melanson, S. J.; Sakata, K.; DiCosmo, F. Improved growth and taxol yield in developing calli of Taxus cuspidata by medium composition. Biotechnology 1993, 11, 731-734.
100. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Gayle, K. S. Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissolute. J. Org. Chem. 1990, 55, 4912-4915.
101. Ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol. Biochemistry 1996, 35, 243-250.
102. Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. 2-Chloro-2'- deoxyadenosine, an antileukemic drug, has an early effect on cellular mitochondrial function. Mol. Pharmacol. 1997, 52, 613-619.
103. Jordan, M. A. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr. Med. Chem. Anti-Cancer Agents 2002, 2, 1-17.
104. Gunasekera, S. P.; Longley, R. E.; Isbrucker, R. A. Acetylated analogues of the microtubule-stabilizing agent discodermolide: preparation and biological activity. J. Nat. Prod. 2001, 64, 171-174.
105. Gunasekera, S. P.; Longley, R. E.; Isbrucker, R. A. Semisynthetic analogues of the microtubulestabilizing agent discodermolide: preparation and biological Activity J. Nat. Prod. 2002, 65, 1830-1837.
106. Hung, D. T.; Narenberg, J. B.; Schreiber, S. L. Syntheses of discodermolides useful for investigating microtubule binding and stabilization. J. Am. Chem. Soc. 1996, 118, 11054-11080.
107. Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. C. Total synthesis of (-)-discodermolide: an application of a chelation-controlled alkylation reaction. J. Org. Chem. 1997, 62, 6098-6099.
108. Marshall, J. A.; John, B. A. Total synthesis of (+)-discodermolide. J. Org. Chem. 1998, 63, 7885-7892.
109. Smith, A. B.; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qiu, Y.; Arimoto, H.; Jones, D. R.; Kobagashi, K. Evolution of a gram-scale synthesis of (+)-discodermolide. J. Am. Chem. Soc. 2000, 122, 8654-8664.
110. Patersen, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Total synthesis of the antimicrotubule agent (+)-discodermolide using boronmediated aldol reactions of chiral ketones. Angew. Chem. Int. Ed. 2000, 39, 377-380.
111. Shaw, S. J.; Sudermann, K. F.; Burlingame, M. A.; Myles, D. C.; Freeze, B. S.; Xian, M.; Brouard, I.; Smith III, A. B. Toward understanding how the lactone moiety of discodermolide affects activity. J. Am. Chem. Soc. 2005, 127, 6532-6533.
112. McGown, A. T.; Fox, B. W. Differential cytotoxicity of combretastatins A1 and A4 in two daunorubicin-resistant P388 cell lines. Cancer Chemother. Pharmacol. 1990, 26, 79-81.
113. El-Zayat, A. A. E.; Degen, D.; Drabek, S.; Clark, G. M.; Pettit, G. R.; Von Hoff, D. D. In vitro evaluation of the antineoplastic activity of combretastatin A-4, a natural product from Combretum caffrum (arid shrub). Anticancer Drugs 1993, 4, 19-25.
114. Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. Antineoplastic agents. 291. isolation and synthesis of combretastatins A-4, A-5, and A-6. J. Med. Chem. 1995, 38, 1666-1672.
115. Hamel, E. Antimitotic natural products and their interactions with tubulin. Med. Res. Rev. 1996, 16, 207-231.
116. Ducki, S.; Mackenzie, G.; Lawrence, N. J.; Snyder, J. P. Quantitative structure-activity relationship (5D-QSAR) study of combretastatin-like analogues as inhibitors of tubulin assembly. J. Med. Chem. 2005, 48, 457-465.
117. Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 18, 6984-6991.
118. Talvitie, A.; Mannila, E.; Kolehmainen, E. Syntheses of some biologically active compounds from stilbenes isolated from the bark of Picea abies. Liebigs Ann. Chem. 1992, 399-401.
119. Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin C. M.; Hamet, E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem. 1991, 34, 2579-2588.
120. Ray, K.; Bhattacharya, B.; Biswas, B. B. Role of B-ring of colchicine in its binding to tubulin. J. Biol. Chem. 1981, 256, 6241-6244.
121. Pettit, G. R.; Rhodes, M. R. Antineoplastic agents 389. New syntheses of the combrestatin A-4 prodrug. Anti-cancer Drug Des. 1998, 13, 183-191.
122. Chaplin, D. J.; Pettit, G. R.; Hill, S. A. Anti-vascular approaches to solid tumour therapy: evaluation of combretastatin A4 phosphate. Anticancer Res. 1999, 19, 189-195.
123. Gwaltney, S. L. II.; Imada, H. M.; Barr, K. J.; Li, Q.; Gehrke, L.; Credo, R. D.; Warner, R. B.; Lee, J. Y.; Kovar, P.; Wang, J.; Nukkala, M. A.; Zielinski, N. A.; Frost, D.; Ng, S. C.; Sham, H. L. Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents. Bioorg. Med. Chem. Lett. 2001, 11, 871-874.
124. Hofle, G.; Bedorf, N.; Gerth, K.; Reichenbach, H. German Patent DE 41 38042, 1993; Chem. Abstr. 1993, 120, 52841.
125. Gerth, K.; Bedrof, N.; Hofle, G.; Irschik, H.; Reichenbach, H. Epothilons A and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties. J. Antibiot. 1996, 49, 560-563.
126. Bollag, D. M.; McQuerey, P. A.; Zhu, H.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 1995, 55, 2325-2333.
127. Altmann, K. - H.; Wartmann, M.; O' Reilly, T. Epothilones and related structures - a new class of microtubule inhibitors with potent in vivo antitumor activity. Biochim. Biophys. Acta. 2000, 1470, M79-M91.
128. ®). J. Bio. Chem. 1997, 272, 2534-2541.
129. Altmann, K. - H.; Bold, G.; Caravathi, G.; End, N.; O' Reilly, T.; Wartmann, M. Epothilones and their analogs - potential new weapons in the fight against cancer. Chimia 2000, 54, 612-621.
130. Balog, D. M.; Meng, D.; Kamanecka, T.; Bertinato, P.; Su, D. - S.; Sorensen, E. J.; Danishefsky, S. J. Totalsynthese von (-)-epothilone A. Angew. Chem. 1996, 108, 2976-2978.
131. Su, D. - S.; Meng, D.; Bertinato, P.; Balog, D. M.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y - H.; Chou, T. - C.; He, L.; Horwitz, S. B. Total synthesis of (-)-epothilone B: an extension of the Suzuki coupling method and insights into structure-activity relationships of the epothilones. Angew. Chem. Int. Ed. 1997, 36, 757-759.
132. Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. Total syntheses of epothilones A and B via a macrolactonization-based strategy. J. Am. Chem. Soc. 1997, 119, 7974-7991.
133. Nocolaou, K. C.; Hapworth, D.; King, N. P.; Finlay, M.; Ray, V. Chemistry, biology and medicine of selected tubulin polymerizing agents. Pure Appl. Chem 1999, 71, 989-997.
134. Zhu, B.; Panek, J. S. Total synthesis of epothilone A. Org. Lett. 2000, 2, 2575-2578.
135. Meng, D.; Su, D. S.; Balog, A.; Bertinato, P.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y. H.; Chou, T. C.; He, L.; Horwitz, S. B. Remote effects in macrolide formation through ring-forming olefin metathesis: an application to the synthesis of fully active epothilone congeners. J. Am. Chem. Soc. 1997, 119, 2733-2734.
136. Altmann, K. - H.; Gertsch, J. Anticancer drugs from nature-natural products as a unique source of new microtubule-stabilizing agents. Nat. Prod. Rep. 2007, 24, 327-357.
137. Chou, T. -C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Design and total synthesis of a superior family of epothilone analogues, which eliminate xenograft tumors to a nonrelapsable state. Angew. Chem. Int. Ed. 2003, 42, 4762-4767.