Chapter 13 History and Future Prospects of Camptothecin and Taxol

Alkaloids: Chemistry and Biology

Volumn 50, Issue C, 1998, Pages 509-536

  Wall, Monroe E ^a   Wani, Mansukh C ^a  

^a RTI INTERNATIONAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007369482     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1099-4831(08)60051-6     Document Type: Article

References (123)

1. Wall M.E., Wani M.C., Cook C.E., Palmer K.H., McPhail A.T., and Sim G.A. J. Am. Chem. Soc. 88 (1966) 3888
2. Wall M.E., Wani M.C., and Taylor H. Cancer Chemother. Repts. 60 (1976) 1011
3. Wall M.E., and Wani M.C. Cancer Res. 55 (1995) 753
4. Hsiang Y.-H., Hertzberg R., Hecht S., and Liu L.F. J. Biol. Chem. 260 (1985) 14873
5. Wall M.E., Wani M.C., Nicholas A.W., Manikumar G., Tele C., Moore L., Truesdale A., Leitner P., and Besterman J.M. J. Med. Chem. 36 (1993) 2689
6. Wall M.E., and Wani M.C. In: Saxton J.E. (Ed). The Monoterpenoid Indole Alkaloids (1994), Wiley, New York 689
7. Perdue, Jr., R.L., Smith, R.E., Wall, M.E., Hartwell, J.L. and Abbott, B.J., Technical Bulletin, No. 1415, U.S. Department of Agriculture, Agricultural Research Service, Washington, DC, 1970
8. Gottlieb J.A., and Luce J.K. Cancer Chemother. Rep. Part I 56 (1972) 103
9. Moertel C.G., Schutt A.J., Reitemerer R.G., and Hahn R.G. Cancer Chemother. Rep. Part I 56 (1972) 95
10. Muggia F.M., Creaven P.J., Jansen H.H., Cohen M.N., and Selawry D.S. Cancer Chemother. Rep. Part I 56 (1972) 515
11. Wani M.C., Ronman P.E., Lindley J.T., and Wall M.E. J. Med. Chem. 23 (1980) 554
12. Abelson H.T., and Penman S. Nature New Biol. 237 (1972) 144
13. Horwitz S.B., Chang C., and Grollman A.P. Mol. Pharmacol. 7 (1971) 632
14. Kessel D., Bosmann H.B., and Lohr K. Biochem. Biophys. Acta 269 (1972) 210
15. Giovanella B.C., Stehlin J.S., Wall M.E., Wani M.C., Nicholas A.W., Liu L.F., Silber R., and Potmesil M. Science 246 (1989) 1046
16. Potmesil M., Hsiang Y.-H., Liu L.F., Bank B., Grossberg H., Kirschenbaum S., Forlenzar T.J., Penziner A., Kanganis D., Knowles D., Traganos F., and Silber R. Cancer Res. 48 (1988) 3537
17. Cai J.C., and Hutchinson C.R. In: Saxton J.E. (Ed). Indoles, Part 4: The Monoterpenoid Indole Alkaloids (1983), Wiley-Interscience, Chichester 753
18. Wall M.E., Wani M.C., Natschke S.M., and Nicholas A.W. J. Med. Chem. 29 (1986) 1553
19. Wani M.C., Nicholas A.W., Manikumar G., and Wall M.E. J. Med. Chem. 30 (1987) 1774
20. Wani M.C., Nicholas A.W., and Wall M.E. J. Med. Chem. 30 (1987) 2317
21. Ejima A., Teresawa H., Sugimori M., and Tagawa H. J. Chem. Soc. Perkin Trans. 1 (1990) 27
22. Jew S., Ok K., Kim H., Kim M.G., Kim J.M., Hah J.M., and Cho Y. Tetrahedon Asymm. 6 (1995) 1245
23. Comins D.L., Bavesky M.F., and Hong H. J. Am. Chem. Soc. 114 (1992) 10971
24. Fang F.G., Xie S., and Lowery M.W. J. Org. Chem. 59 (1994) 6142
25. Wani M.C., and Wall M.E. J. Org. Chem. 34 (1969) 1364
26. Wall M.E., and Wani M.C. In: Wagner H., Hikino H., and Farnsworth N.R. (Eds). Economic and Medicinal Plant Research 5 (1991), Academic Press, London 111
27. Wall M.E., and Wani M.C. In: Kinghorn A.D., and Balandrin M.F. (Eds). Human Medicinal Agents from Plants (1993), American Chemical Society, Washington, DC 149 ACS Symposium Series, No. 534
28. Nicholas A.W., Wani M.C., Manikumar G., Wall M.E., Kohn K.W., and Pommier Y. J. Med. Chem. 33 (1990) 972
29. Hertzberg R.P., Caranfa M.J., Holden K.G., Jakas D.R., Gallagher G., Mattern M.R., Mong S.-M., Bartus J.O., Johnson R.K., and Kingsbury W.D. J. Med. Chem. 32 (1989) 715
30. Sugasawa T., Toyoda T., Uchido J., and Yamaguchi K. J. Med. Chem. 19 (1976) 675
31. Wani M.C., Nicholas A.W., and Wall M.E. J. Med. Chem. 29 (1986) 2358
32. Peel M.R., Milstead M.W., Sternbach D., Besterman J.M., Leitner P., Morton B., Wall M.E., and Wani M.C. Bioorg. Med. Chem. Lett. 5 (1995) 2129
33. Sawada S., Okajima S., Aiyama R., Nokata K., Furuta T., Yokokura T., Sugino E., Yamaguchi K., and Miyaska T. Chem. Pharm. Bull. 39 (1991) 1446
34. Kingsbury W.D., Boehm J.C., Jakas D.R., Holden K.G., Hecht S.M., Gallagher G., Caranfa M., McCabe F.L., Faucette L.R., Johnson R.K., and Hertzberg R.P. J. Med. Chem. 34 (1991) 98
35. Luzzio M.J., Besterman J.M., Emerson D.L., Evans M.G., Lackey K., Leitner P.L., McIntyre G., Morton B., Myers P.L., Peel M., Sisco J.M., Sternbach D., Tong W.-Q., Truesdale A., Uehling D.E., Vuong A., and Yates J. J. Med. Chem. 38 (1995) 395
36. Giovanella B.C., Hinz H.R., Kozielski A.J., Stehlin Jr. J.S., Silber R., and Potmesil M. Cancer Res. 51 (1991) 3052
37. Potmesil M., Giovanella B.C., Wall M.E., Liu L.F., Silber R., Stehlin J.S., Wani M.C., and Hochster H. In: Andoh T., Ikeda H., and Oguro M. (Eds). Molecular Biology of DNA Topoisomerases and Its Application to Chemotherapy (1993), CRC Press, Boca Raton, FL 301
38. Stehlin J.S., Natelson E.A., Hinz H.R., Giovanella B.C., de Ipolyi P.D., Fehir K.M., Trezona T.P., Vardeman D.M., Harris N.J., Marcel A.K., Kozielski A.J., and Ruiz-Razura A. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 59
39. Jaxel C., Kohn K.W., Wani M.C., Wall M.E., and Pommier Y. Cancer Res. 49 (1989) 1465
40. Hsiang Y., Liu L.F., Wall M.E., Wani M.C., Nicholas A.W., Manikumar G., Kirschenbaum S., Siliber R., and Potmesil M. Cancer Res. 49 (1989) 4385
41. Giovanella B.C., Stehlin J.S., Wall M.E., Wani M.C., Nicholas A.W., Liu L.F., Silber R., and Potmesil M. Science 246 (1989) 1046
42. Potmesil M., Giovanella B.C., Liu L.F., Wall M.E., Silber R., Stehlin Jr. J.S., Hsiang Y.-H., and Wani M.C. In: Potmesil M., and Kohn K.W. (Eds). DNA Topoisomerases in Cancer (1991), Oxford University Press, New York 299
43. Hinz H., Harris N., Natelson E., and Giovanella B. Cancer Res. 54 (1994) 3096
44. Pantazis P., Early J.A., Kozielski A.J., Mendoza J.T., Hinz H.R., and Giovanella B. Cancer Res. 53 (1993) 1577
45. Pantazis P., Kozielski A.J., Mendoza J.T., Early J.A., Hinz H.R., and Giovanella B.C. Cancer Res. 53 (1993) 863
46. Pantazis P., Mendoza J.T., Kozielski A.J., Natelson E.A., and Giovanella B.C. Eur. J. Haematol. 50 (1993) 81
47. Kunimoto T., Nitta K., Tanaka T., Uehara N., Baba H., Takeuchi M., Yokokura T., Sawada S., Miyasaka T., and Mutai M. Cancer Res. 47 (1987) 5944
48. Tsuruo T., Matsuzaki T., Matsushita M., Saito H., and Yokokura T. Cancer Chemother. Pharmacol. 21 (1988) 71
49. Kawato Y., Furuta T., Aonuma M., Yasuoka M., Yokokura T., and Matsumoto K. Cancer Chemother. Pharmacol. 28 (1991) 192
50. Houghton P.J., Cheshire P.J., Hallman J.C., Bissery M.C., Mathieu-Boue A., and Houghton J. Cancer Res. 53 (1993) 2823
51. Taguchi T. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 67
52. Rothenberg M.L., Rowinsky E.K., Kuhn J.G., Burris III H.A., Donehower R.C., and Von Hoff D.D. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 75
53. Chabot G.G., de Forni M., Abigerges D., Armand J.-P., Clavel M., Bugat R., Culine S., Extra J.-M., Marty M., Bissery M.-C., Mathieu-Boue A., Herait P., and Gouyette A. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 83
54. Masuda N., Fukuoka M., Kudoh S., Kusunoki Y., Matsui K., Nakagawa K., Hirashima T., Tamanoi M., Nitta T., Yana T., and Negoro S. J. Clin. Oncol. 12 (1994) 90
55. Shimada Y., Sasaki Y., Sugano K., Shirao K., Kondo H., Yokota T., Saito D., Tamura T., Ohe Y., Shinkai T., Eguchi K., Saijo N., and Shintani S. Proc. Am. Soc. Clin. Oncol. 12 (1993) 196
56. Fukuoka M., Niitani H., Suzuki A., Motomiya M., Hasegawa K., Nishiwaki Y., Kuriyama T., Ariyoshi Y., Negoro S., and Masuda N. J. Clin. Oncol. 10 (1992) 16
57. Johnson, R.K., Hertzberg, R.P., Kingsbury, W.D., Boehm, J.C., Caranfa, M.J., Faucette, L.F., McCabe, F.L. and Holden, K.G., Proc. 6th NCI-EORTC Symposium on New Drugs in Cancer Therapy, Annals of Oncology, A301, Amsterdam, March 1989
58. Johnson, R.K., McCabe, F.L., Gallagher, G., Wood, J., Gelef, J. and Hertzberg, R.P., Proc. 7th NCI-EORTC Symposium on New Drugs in Cancer Therapy, Annals of Oncology, Vol. 3, Suppl. 1, p. 85, Amsterdam, 1992
59. Houghton P.J., Cheshire P.J., Myers L., Stewart C.F., Synold T.W., and Houghton J.A. Cancer Chemother. Pharmacol. 31 (1992) 229
60. Hochster H.S. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 93
61. Verweij J., Huinink W.B., Lund B., Planting A., Beijner J., de Boer-Dennert M., Rosing H., Koier I., and Hansen H. In: Potmesil M., and Pinedo H. (Eds). Camptothecins: New Anticancer Agents (1995), CRC Press, Boca Raton, FL 105
62. Anzai H., Frost P., and Abbruzzese J.L. Proc. Am. Assoc. Cancer Res. 33 (1992) 431
63. Miller A.A., Hargis J.B., Fields S., Lilenbaum R.C., Rosner G.L., and Schilsky R.L. Proc. Am. Soc. Clin. Oncol. 12 (1993) 399
64. Lilenbaum, R.C., Rosner, G.L., Ratain, M.J., Hargis, J.B., Miller, A.A., Green, M.R. and Schilsky, R.L., Proc. Am. Soc. Clin. Oncol. 13, Abst. 319 (1994)
65. Emerson D.L., Besterman J.M., Brown H.R., Evans M.G., Leitner P.P., Luzzio M.J., Shaffer J.E., Sternbach D.D., Vehling D., and Vuong A. Cancer Res. 55 (1995) 603
66. Kunka R., O'Dwyer P., Cassidy J., DePee S., Littlefield D., Selinger K., Collis P., Beranek P., and Wissel P. Proc. Annu. Mtg. Am. Assoc. Cancer Res. 36 (1995) A1397
67. Mitsui I., Kumazawa E., Hirota Y., Aonuma M., Sugimori M., Ohsuki S., Uoto K., Ejima A., Terasawa H., and Sato K. Japanese J. Cancer Res. 86 (1995) 776
68. Potmesil M. Cancer Res. 54 (1994) 1431
69. Wall M.E. In: Lednicer D. (Ed). Chronicles of Drug Discovery III (1993), American Chemical Society, Washington, DC 327-348
70. Suffness M., and Wall M.E. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 3-25
71. Wall, M.E. and Wani, M.C., Abstracts of Papers, 153rd National Meeting of the American Chemical Society, Miami Beach, FL, No. M-006, 1967
72. Wani M.C., Taylor H.L., Wall M.E., Coggin P., and McPhail A.T. J. Am. Chem. Soc. 83 (1971) 2325
73. Wall M.E., and Wani M.C. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives 9 (1995), Elsevier, New York 1-22
74. Suffness M. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 1-17 ACS Symposium, Series 583
75. Fuchs D.A., and Johnson R.K. Cancer Treat. Rep. 62 (1978) 1219
76. Schiff P.B., Fant J., and Horwitz S.B. Nature 22 (1979) 665
77. Horwitz S.B., Parness J., Schiff P.B., and Manfredi J.J. Cold Spring Harbor Symp. Quant. Biol. 46 (1982) 219
78. Horwitz S.B. Trends Pharmacol. Sci. 13 (1992) 134
79. Campbell S.J., and Whitney S.A. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 58-71 ACS Symposium, Series 583
80. Croom Jr. E.M. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 37-70
81. Chauvière G., Guénard D., Picot F., Sénilh V., and Potier P. C. R. Acad. Sci. Paris, Ser. II 193 (1981) 501
82. Sénilh V., Blechert S., Colin M., Guénard D., Picot F., Potier P., and Varenne P. J. Nat. Prod. 47 (1984) 131
83. Stierle A., Stierle D., Strobel G., Bignami G., and Grothaus P. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 81-97 ACS Symposium Series 583
84. Stierle A., Strobel G., and Stierle D. Science 260 (1993) 214
85. Strobel G.A., Stierle A., Stierle D., and Hess W.M. Mycotaxon 47 (1993) 71
86. Gibson D.M., Ketchum R.E.B., Hirasuna T.J., and Shuler M.I. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 71-96
87. Kingston D.G.I. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 203-216 ACS Symposium, Series 583
88. Georg G.I., Harriman G.C.B., Vander Velde D.G., Boge T.C., Cheruvallath Z.S., Datta A., Hepperle M., Park H., Himes R.H., and Jayasinghe L. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 217-232 ACS Symposium, Series 583
89. Gueritte-Voeglein F., Tuenard E., Dubois J., Wahl A., Marder R., Muller R., Lund M., Bricard L., and Potier P. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 189-202 ACS Symposium, Series 583
90. Commercon A., Bourzat J.D., Didier E., and Lavelle F. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 233-246 ACS Symposium, Series 583
91. Holton R.A., Biediger R.J., and Boatman P.D. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 97-122
92. Chauvière G., Guénard D., Picot F., Sénilh V., and Potier P. C. R. Acad. Sci. Parts, Ser. II 293 (1981) 501
93. Sénilh V., Guéritte F., Guénard D., Colin M., and Potier P. C. R. Acad. Sci. Paris, Ser. II 299 (1984) 1039
94. Denis J.-N., Greene A.E., Guénard D., Guéritte-Voegelein F., Mangatal L., and Potier P. J. Am. Chem. Soc. 110 (1988) 5917
95. Denis J.-N., Greene A.E., Serra A.A., and Luche M.-J. J. Org. Chem. 51 (1986) 46
96. Kanazawa A.M., Denis J.-N., and Greene A.E. J. Org. Chem. 59 (1994) 1238
97. Georg G.I. Tetrahedron Lett. 25 (1984) 3779
98. Georg G.I., Kant J., and Gill H.J. J. Am. Chem. Soc. 109 (1987) 1129
99. Ojima I., Habus I., Zhao M., Georg G.I., and Jayasinghe L. J. Org. Chem. 56 (1991) 1681
100. Georg G.I., Cheruvallath Z.S., Himes R.H., Mejillano M.R., and Burke C.T. J. Med. Chem. 35 (1992) 4230
101. Ojima I., Habus I., Zhao M., Zucco M., Park Y.H., Sun C.M., and Brigaud T. Tetrahedron 48 (1992) 6985
102. Goerg G.I., Cheruvallath Z.S., Harriman G.C.B., Hepperle M., and Park H. Bioorg. Med. Chem. Lett. 3 (1993) 2467
103. Holton, R.A., U.S. Patent No. 5,175,315(1992)
104. Holton R.A., Biediger R.J., and Boatman P.D. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 112-113
105. Holton, R.A., U.S. Patent No. 5,229,526; 5,274,124(1993)
106. Bourzat J.D., and Commercon A. Tetrahedron Lett. 34 (1993) 6049
107. Didier E., Fouque E., Taillepied I., and Commercon A. Tetrahedron Lett. 35 (1994) 2349
108. Didier E., Fouque E., and Commercon A. Tetrahedron Leu. 35 (1994) 3063
109. Holton R.A., Somoza C., Kim H.B., Liang F., Biediger R.J., Boatman P.D., Shindo M., Smith C.C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K.K., Gentile L.N., and Liu J.H. J. Am. Chem. Soc. 116 (1994) 1597
110. Holton R.A., Kim H.B., Somoza C., Liang F., Biediger R.J., Boatman P.D., Shindo M., Smith C.C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K.K., Gentile L.N., and Liu J.H. J. Am. Chem. Soc. 116 (1994) 1599
111. Holton R.A., Somoza C., Kim H.-B., Liang F., Biediger R.J., Boatman P.D., Shindo M., Smith C.C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K.K., Gentile L.N., and Liu J.H. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 288-301 ACS Symposium, Series 583
112. Nicolaou C., Yang Z., Liu J.J., Ueno H., Nantermet P.G., Guy R.K., Claiborne C.F., Renaud J., Couladouros E.A., Paulvannan K., and Sorensen E.J. Nature 367 (1994) 630
113. Nicolaou K.C., and Guy R.K. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 302-311 ACS Symposium, Series 583
114. Kingston D.G.I. In: Kinghorn A.D., and Balandrin M.F. (Eds). Human Medicinal Agents from Plants 534 (1993), American Chemical Society, Washington, DC 138-148
115. Kingston D.G.I. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 203-216 ACS Symposium, Series 583
116. Georg G.I., Harriman G.C.B., Vander Velde D.G., Boge T.C., Cheruvallath A.S., Datta A., Hepperle M., Park H., Himes R.H., and Jayasinghe L. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 217-231 ACS Symposium, Series 583
117. Georg G.I., Boge T.C., Cheruvallath A.S., Clowers J.S., Harriman G.C.B., Hepperle M., and Park H. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 317-378
118. Gueritte-Voegelein F., Guénard D., Dubois J., Wahl A., Marder R., Muller R., Lund M., Bricard L., and Potier P. In: Georg G.I., Chen T.T., Ojima I., and Vyas D.M. (Eds). Taxane Anticancer Agents (1995), American Chemical Society, Washington, DC 189-202 ACS Symposium, Series 583
119. Arbuck S.G., and Blaylock B.A. In: Suffness M. (Ed). Taxol: Science and Applications (1995), CRC Press, Boca Raton, FL 379-415
120. Rowinsky E.K., Chaundhry V., Cornblath D.R., and Donehower R.C. Monogr. Natl. Cancer Inst. 15 (1993) 107
121. Weiss R., Donehower R.C., Wiemik P.H., Ohnuma T., Gralla R.J., Trump D.L., Baker Jr. J.R., Van Echo D.A., Von Hoff D.D., and Leyland-Jones B. J. Clin. Oncol. 8 (1990) 1263
122. Nicolaou K.C., Riemer C., Kerr M.A., Rideout D., and Wrasidlo W. Nature 364 (1993) 464
123. Sharpless V., Li G., and Chang H.-T. Angew. Chem. Int. Ed. 35 (1996) 451