Monoterpenoid Indole Alkaloids, CNS and Anticancer Drugs

Analogue-Based Drug Discovery II

Volumn , Issue , 2010, Pages 189-215

  Nemes, András ^a  

^a GEDEON RICHTER LTD   (Hungary)

Author keywords

Antitumor agents; Camptothecin derivatives; Cerebral insufficiencies; Dimer complex; Dimeric vinca alkaloids; Monoterpenoid indole alkaloids; Small cell lung cancer; Structure activity relationships; Ternary complex; Topoisomerase; Tubulin; Vincamine derivatives

Indexed keywords

EID: 84887230671     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630035.ch8     Document Type: Chapter

References (151)

1. Herbert, R.B. (1994) The biosynthesis of terpenoid indole alkaloids, in The Monoterpenoid Indole Alkaloids, Supplement to Indoles, Part 4 (ed. J.E. Saxton), Wiley-InterScience, Chichester, pp. 1-13.
2. Le Men, J. and Taylor, W.I. (1965) Uniform numbering system for indole alkaloids. Experientia, 21, 508-510.
3. Lo{double acute}rincz, C., Szász, K., and Kisfaludy, L. (1976) The synthesis of ethylapovincaminate. Arzneim.-Forsch., 26, 1905-1908.
4. (1975) Levorotatory, dextrorotatory and racemic eburnamonines, Fr. Patent 2 268 016, Omnium Chimique S.A.
5. Lacroix, P., Quiniou, M.J., Linée, P., and Le Polles, J.B. (1979) Cerebral metabolic and hemodynamic activities of 1- eburnamonine in the anesthetized dog. A comparison with vincamine. Arzneim.- Forsch., 29, 1094-1101.
6. De Noble, V.J., Repetti, S.J.,Gelpke, L.W., Wood, L.M., and Keim, K.L. (1986) Vinpocetine: nootropic effects of a stepthrough passive-avoidance response in rats. Pharmacol. Biochem. Behav., 24, 1123-1128.
7. King, G.A. (1987) Protective effects of vinpocetine and structurally related drugs on the lethal consequences of hypoxia in mice. Arch. Int. Pharmacodyn. Ther., 286, 299-307.
8. Kushiku, K., Katsuragi, T., Mori, R., Morishita, H., and Furukawa, T. (1985) Cardiovascular effects of brovincamine and possible mechanisms. Clin. Exp. Pharmacol. Physiol., 12, 121-130.
9. Tonomoto, M., Hatta, S., Nagata, M., Takahashi, Y., and Tamai, A. (1998) Blood flow changes in optic nerve head of albino rabbits following intravenous administration of brovincamine fumarate. Yonago Acta Med., 41, 89-97.
10. Czibula, L., Nemes, A., Visky, G., Farkas, M., Szombathelyi, Z., Kárpáti, E., Sohár, P., Kessel, M., and Kreidl, J. (1993) Syntheses and cardiovascular activity of stereoisomers and derivatives of eburnane alkaloids. Liebigs. Ann. Chem., 221-229.
11. Szombathelyi, Z., Kárpáti, E., Kalaus, G., Szabó, L., and Szántay, C. (1991) Vasodilator and angioprotective activity of 1-ethyl-1-hydroxyalkyloctahydroindolo[2,3-a]quinolizine derivatives. Arzneim.-Forsch., 41, 621-625.
12. Barzaghi, F., Dragonetti, M., Formento, M.L., Gueniau, C., Nencioni, A., and Mantegazza, P. (1986) A comparison of some of the pharmacological properties of vindeburnol with those of vincamine, vinburnine, dihydroergotoxine and nicergoline. Arznneim.-Forsch., 36, 1442-1448.
13. Kawasima, Y., Ikemoto, T., Horiguchi, A., Hayashi, M.,Matsumoto, K., Kawarasaki, K., Yamazaki, R., Okuyama, R., and Hatayama, K. (1993) Synthesis and pharmacological evaluation of (nitrooxy) alkyl apovincaminate. J. Med. Chem., 36, 815-819.
14. Nemes, A., Czibula, L., Szántay, C., Jr., Gere, A., Laszy, J., Gyertyán, I., Szombathelyi, Z., and Szántay, C. (2008) Synthesis and evaluation of 2- hydroxyethyl-trans-apovincaminate derivatives as antioxidant and cognitive enhancer agents. J. Med. Chem., 51, 479-486.
15. Hugel, G., Massiot, G., Levy, J., and Le Men, J. (1981) Méthyléne-indolines, indolénines et indoléniums-XIII: L?hydroxy-16-déhydro-1 vincadifformine, intérmédiaire dans le rearrangement biomimetique de la vincadifformine en vincamine. Tetrahedron, 37, 1369-1375.
16. Bernardelli, G. (1986) Vincamine, Ger. Offen. 3606665, Arysearch Arylan AG.
17. Szántay, C. and Nemes, A. (1994) The eburnamine-vincamine group, in The Monoterpenoid Indole Alkaloids, Supplement to Indoles, Part 4 (ed. J.E. Saxton), Wiley-InterScience, Chichester, pp. 437-486.
18. Nemes, A., Czibula, L., Visky, G., Farkas, M., and Kreidl, J. (1991) Alternative routes to vincamine. Heterocycles, 32, 2329-2338.
19. Nemes, A., Kreidl, J., Czibula, L., Nógrádi, K., Farkas, M., Szántay, C., Jr., Tárkányi, G., Juhász, I., Kálmán, A., and Párkány, L. (2000) Synthesis of pentacyclic ring systems, indolo[2,3-a] [1,2]oxazino[5,6-i]quinolizine and indolo [2,3-a] pyrano[3,2-i]quinolizine, and their application for the synthesis of eburnamine-vincamine alkaloids. Heterocycles, 53, 1697-1711.
20. Wotchal, B.E. and Tschapidze, G.E. (1965) DasVerhalten der peripherenGefässe bei der hypertoniekrankheit. Ther. Hung., 13, 3-6.
21. Schlittler, E. and Bein, H.J. (1967) Antihypertensive Agents (ed. E. Schlittler), Academic Press, New York, pp. 191-221.
22. Hagiwara, M., Endo, T., and Hidaka, H. (1984) Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle. Biochem. Pharmacol., 33, 453-457.
23. Beavo, J.A. (1995) Cyclic nucleotide phosphodiesterases: functional implications of multiple isoforms. Physiol. Rev., 75, 725-748.
24. Hayakawa, M. (1992) Comparative efficacy of vinpocetine, pentoxyfilline and nicergoline on red blood cell deformability. Arzneim.-Forsch., 42, 108-111.
25. Molnár, P. and Erdo{double acute} S.L. (1995) Vinpocetine is as potent as phentoin to block voltage-gated Na+ channels in rat cortical neurons. Eur. J. Pharmacol., 273, 303-306.
26. Tretter, L. and Adam-Vizi, V. (1998) The neuroprotective drug vinpocetine prevents veratridine-induced [Na+]i and [Ca2+]i rise in synaptosomes. Neuroreport, 9, 1849-1853.
27. Sitges, M. and Nekrassov, V. (1999) Vinpocetine selectively inhibits neurotransmitter release triggered by sodium channel activation. Neurochem. Res., 24, 1585-1591.
28. Chinopoulos, C., Tretter, L., Rozsa, A., and Adam-Vizi, V. (2000) Exacerbated responses to oxidative stress by an Na(+) load in isolated nerve terminals. The role of ATP depletion and rise of [Ca(2+)]i. J. Neurosci., 20, 2094-2103.
29. Bönöck, P., Gulyás, B., Adam-Vizi, V., Nemes, A., Kárpáti, E., Kiss, B., Kapás, M., Szántay, C., Koncz, I., Zelles, T., and Vas, á. (2000) Role of sodium channel inhibition in neuroprotection: effect of vinpocetine. Brain Res. Bull., 53, 245-254.
30. Tanaka, Y., Morimoto, K., Ishii, K., and Nakayama, K. (1994) Calcium antagonistic vasodilator mechanisms of brovincamine fumarate studied in canine cerebral artery. Arzneim.-Forsch., 44, 803-808.
31. Kaneko, S., Takahashi, H., and Satoh, M. (1990) The use of Xenopus oocytes to evaluate drugs affecting brain Ca2+ channels: effect of bifemelane and several nootropic agents. Eur. J. Pharmacol., 189, 51-58.
32. Zelles, T., Franklin, L., Koncz, I., Lendvai, B., and Zsilla, G. (2001) The nootropic drug vinpocetine inhibits veratridine induced [Ca2+]i increase in rat hippocampal CA1 pyramidal cells. Neurochem. Res., 26, 1095-1100.
33. Miyamoto, M., Murphy, T.H., Schnaar, R.L., and Coyle, J.T. (1989) Antioxidants protect against glutamate-induced cytotoxicity in a neuronal cell line. J. Pharmacol. Exp. Ther., 250, 1132-1140.
34. Erdo{double acute} S.L., Cai, N.S.,Wolff, J.R., and Kiss, B. (1990) Vinpocetine protects against excitotoxic cell death in primary cultures of rat cerebral cortex. Eur. J. Pharmacol., 187, 551-553.
35. Vereczkey, L. (1985) Pharmacokinetics and metabolism of vincamine and related compounds. Eur. J. Drug Metab. Pharmacokinet., 10, 89-103.
36. Mayo, B.C., Biggs, S.R., Hawkins, D.R., Chasseaud, L.F., Darragh, A., and Leaf, F.C. (1985) The metabolic fate of 11- bromo[15 3H]vincamine in man. Eur. J. Drug Metab. Pharmacokinet., 10, 189-196.
37. Sado, P.A., Gibassier, D., LeVerge, R., Acerbi, D., and Schiantelli, P. (1985) Biodisponsibilité relative de la vinburnine chez l?homme. J. Pharm. Belg., 40, 308-322.
38. Bargheon, J., Durocher, A.M., and Lagrannge, M. (1984) Treatment of cerebrovascular deficiencies. Therapeutic evaluation from 129 cases using the double-blind method against placebo. Sem. Hop., 60, 169-174.
39. Jansen, W., O'Connolly, M., Lehmann, E., and Mayer, M. (1986) Experimental clinical studies on the effect of eburnamonine in cerebrovascular disorders. Pharmacopsychiatry, 19, 389-394.
40. Domini, L., Acciavatti, A., Caligani, C., Saletti, M., De Franco, V., Pecchi, S., Auteri, A., and Di Perri, T. (1990) The effect of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research. Recent Prog. Med., 81, 716-723.
41. Manconi, E., Binaghi, E., and Pitzus, F. (1986) A double-blind clinical trial of vinpocetine in the treatment of cerebral insufficiency of vascular and degenerative origin. Curr. Ther. Res., 40, 702-709.
42. Ballesteri, R., Fontana, L., and Astengo, F. (1987) A double-blind placebo controlled evaluation of the safety and efficacy of vinpocetine in the treatment of patients with cronic vascular senile cerebral dysfuntion. J. Am. Geriatr. Soc., 35, 425-430.
43. Blaha, L., Erzigkeit, H., Adamczyk, A., and Freytag, S. (1989) Clinical evidence of the effectiveness of vinpocetine in the treatment of organic psychosyndrome. Hum. Psychopharmacol., 4, 103-111.
44. Szakáll, S., Boros, I., Balkay, L., Emri, M., Fekete, I., Kerényi, L., Lehel, S., Márián, T., Molnár, T., Varga, J., Galuska, L., Trón, L., Bereczky, D., Csiba, L., and Gulyás, B. (1998) Cerebral effects of a single dose of intravenous vinpocetine in chronic stroke patients: a PET study. J. Neuroimaging, 8, 197-204.
45. Vas, Á., Gulyás, B., Szabó, Z., Bönöczk, P., Csiba, L., Kiss, B., Kárpáti, E., Pánczél, G., and Nagy, Z. (2002) Clinical and nonclinical investigations using positron emission tomography, near infrared spectroscopy and transcranial Doppler methods on the neuroprotective drug vinpocetine: a summary of evidences. J. Neurol. Sci., 203-204, 259-262.
46. Yamaguchi, S., Fukuyama, H., Yonekura, K., and Konishi, J. (1992) Effect of brovincamine on cerebral circulation and metabolism in internal carotid artery occlusion examined by positron emission tomography. Eur. Neurol., 32, 314-317.
47. Koseki, N., Araie, M., Yamagami, J., Shirato, S., and Yamamoto, S. (1999) Effects of oral brovincamine on visual field damage in patients with normal tension glaucoma with low-normal intraocular pressure. J. Glaucoma, 8, 117-123.
48. da Rocha, A.B., Lopes, R.M., and Schwartsmann, G. (2001) Natural products in anticancer therapy. Curr. Opin. Pharmacol., 1, 364-369.
49. Noble, R.L., Beer, C.T., and Cutts, J.H. (1958) Further biological activities of vincaleukoblastine-an alkaloid isolated from Vinca rosea (L.). Biochem. Pharmacol., 1, 347-348.
50. Johnson, I.S., Wright, H.F., Svoboda, G.H., and Vlantis, J. (1960) Antitumor principles derived from Vinca rosea Linn. I. Cancer Res., 20, 1016-1022.
51. Svoboda, G.H., Johnson, I.S., Gorman, M., and Neuss, N. (1962) Current status of research on the alkaloids of Vinca rosea. J. Pharm. Sci., 51, 707-720.
52. Sartorelli, A.C. and Creasey, W.A. (1969) Cancer chemotherapy. Annu. Rev. Pharmacol., 9, 51-72.
53. Noble, R.L. (1990) The discovery of the vinca alkaloids-chemotherapeutic agents against cancer. Biochem. Cell. Biol., 68, 1344-1351.
54. Barnett, C.J., Cullinan, G.J., Gerzon, K., Hoying, R.C., Jones, W.E., Newlon, W.M., Poore, G.A., Robison, R.L., and Sweeney, J.M. (1978) Structure-activity relationships of dimeric Catharanthus alkaloids. 1. Deacetylvinblastine amide (vindesine) sulfate. J. Med. Chem., 21, 88-96.
55. Owen, R.T. (1980) Vindesine. Med. Actual/Drugs Today, 16, 196-201.
56. Prous, J.R. (1990) The years new drugs. Drug News Perspect., 3, 19-29.
57. Conrad, R.A., Cullinan, G.J., Gerzon, K., and Poore, G.A. (1979) Structure-activity relationships of dimeric Catharanthus alkaloids. 2. Experimental antitumor activities of N-substituted deacetylvinblastine amide (vindesine) sulfates. J. Med. Chem., 22, 391-400.
58. Johnson, I.S., Hargrove, W.W., Harris, P.N., Wright, H.F., and Boder, G.B. (1966) Preclinical studies with vinglycinate, one of a series of chemically derived analogs of vinblastine. Cancer Res., 26, 2431-2436.
59. Bhushana Rao, K.S.P., Collard, M.P.M., Dejonghe, J.P., Atassi, G., Hannart, J.A., and Trouet, A. (1985) Vinblastin-23-oyl amino acid derivatives: chemistry, physico-chemical data, toxicity and antitumor activities against P338 and L1210 leukemias. J. Med. Chem., 28, 1079-1088.
60. Miller, J.C. and Gutowski, G.E. (1978). Vinca alkaloid derivatives, Ger. Offen. 2753791, Eli Lilly and Co.
61. Miller, J.C., Gutowski, G.E., Poore, G.A., and Boder, G.B. (1977) Alkaloids of Vinca rosea, L. (Catharanthus roseus G. Don). 38. 40-Dehydrated derivatives. J. Med. Chem., 20, 409-413.
62. Johnson, I.S., Cullinan, G.J., Boder, G.B., Grindey, C.B., and Laguzza, B.C. (1987) Structural modification of the vinca alkaloids. Cancer Treat. Rev., 14, 407-410.
63. Conrad, R.A. (1983). Method of preparing vincristine, US Patent 4,375,432, Ely Lilli and Co.
64. Hill, B.T., Fiebig, H.H., Waud, W.R., Poupon, M.-F., Colpaert, F., and Kruczynsky, A. (1999) Superior in vivo experimental antitumour activity of vinflunine, relative to vinorelbine, in a panel of human tumour xenografts. Eur. J. Cancer, 35, 512-520.
65. Bennouna, J., Delard, J.-P., Campone, M., and Nguyen, L. (2008) Vinflunine: a new microtubule inhibitor agent. Clin. Cancer Res., 14, 1625-1632.
66. Langlois, N., Gueritte, F., Langlois, Y., and Potier, P. (1976) Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids. J. Am. Chem. Soc., 98, 7017-7024.
67. Brossi, A. and Suffness, M.(eds) (1990) Antitumor bisindole alkaloids from Catharanthus roseus (L.), in The Alkaloids, vol. 37, Academic Press, Inc., San Diego.
68. Sapi, J. and Massiot, G. (1994) Bisindole alkaloids, in The Monoterpenoid Indole Alkaloids, Supplement to Indoles, Part 4 (ed J.E. Saxton), Wiley-InterScience, Chichester, pp. 523-646.
69. Jovanovics, K., Szász, K., Fekete G., Bittner, E., Dezséri, E., and Éles, J. (1975) Chromic oxidation of vinblastine sulfate to form vincristine, US Patent 3,899,493, G. Richter Ltd 70.
70. Conrad, R.A. (1982) Vinca dimer, EP37 290, Eli Lilly Co.
71. Mangeney, P., Andrimialisoa, R.Z., Lallemand, J.Y., Langlois, N., Langlois, Y., and Potier, P. (1979) 50- Noranhydrovinblastine. Tetrahedron, 35, 2175-2179.
72. Sudakin, V. and Yen, T.J. (2007) Targeting mitosis for anti-cancer therapy. Biodrugs, 21, 225-233.
73. Sackett, D.L. (1995) Vinca site agents induce structural changes induced in tubulin different from and antagonistic to changes induced by colchicine site agents. Biochemistry, 34, 7010-7019.
74. Borman, L.S. and Kuehne, M.E. (1987) Proc. Annu. Meet. Assoc. Cancer Res., 28, 331-339.
75. Binet, S., Chaineau, E., Fellous, A., Lataste, H., Krikorian, A., Couzinier, J.-P., and Meininger, V. (1990) Immunofluorescence study of the action of navelbine, vincristine and vinblastine on mitotic and axonal microtubles. Int. J. Cancer, 46, 262-266.
76. Ngan, V.K., Bellman, K., Panda, D., Hill, B.T., Jordan, M.A., and Wilson, L. (2000) Novel actions of the antitumor drugs vinflunine and vinorelbine on microtubules. Cancer Res., 60, 5045-5051.
77. van Tellingen, O., Beinen, J.H., Nooijen, W.J., and Bult, A. (1993) Plasma pharmacokinetics of vinblastine and the investigational vinca alkaloidN-(deacetyl- O-4-vinblastoyl-23)-L-ethyl isoleucinate in mice. Cancer Res., 53, 2061-2065.
78. Rahmani, R. and Zhou, X.J. (1993) Pharmacokinetics and metabolism of vinca alkaloids. Cancer Surv., 17, 269-281.
79. Schlaifer, D., Cooper, M.R., Attal, M. et al. (1993) Myeloperoxidase: an enzyme involved in intrinsic vincristine resistance in human myeloblastic leukemia. Blood, 81, 482-489.
80. Wargin, W.A. and Lucas, V.S. (1994) The clinical pharmacokinetics of vinorelbine. Semin. Oncol., 21, 21-27.
81. Lampidis, T.J., Kolonias, D., Savaraj, N., and Rubin, R.W. (1992) Cardiostimulatory and antiarrhytmic activity of tubulin-binding agents. Proc. Natl. Acad. Sci. USA, 89, 1256-1260.
82. Hacker, M.P. (1992) The Toxicity of Anticancer Drugs (eds G. Powisand M.P. Hacker), Pergamon Press, New York, p. 152.
83. Borst, P., Evers, R., Kool, M., and Wijnholds, J. (2000) A family of drug transporters: the multidrugresistance-associated proteins. J. Natl. Cancer Inst., 16, 1295-1302.
84. Zhou, S.F., Wang, L.L., Di, Y.M., Xue, C.C., Duan,W., Li, C.G., and Li, Y. (2008) Substrates and inhibitors of human multidrug resistance associated proteins and the implications in drug development. Curr. Med. Chem., 15, 1981-2039.
85. Luker, K.E., Pica, C.M., Schreiber, R.D., and Piwnica-Worms, D. (2001) Overexpression of IRF9 confers resistance to antimicrotubule agents in breast cancer cells. Cancer Res., 61, 6540-6547.
86. Furuse, K., Fukuoka, M., Kawahara, M., Nishikawa, H., Takada, Y., Kudoh, S., Katagami, N., and Ariyoshi, Y. (1999) Phase III study of concurrent versus sequential thoracic radiotherapy in combination with mitomycin, vindesine, and cisplatin in unresectable stage III non-small-cell lung cancer. J. Clin. Oncol., 17, 2692-2699.
87. Friedel, G., Hruska, D.,Budach,W.,Wolf, M., Kyriss, T., Hurtgen, M., Eulenbruch, H.-P., Dierkesmann, R., and Toomes, H. (2000) Neoadjuvant chemo-radiotherapy of stage III non-small-cell lung cancer. Lung Cancer, 30, 175-185.
88. Kodani, T., Ueoka, H., Kiura, K., Tabata, M., Takigawa, N., Segawa, J., Moritaka, T., Hiraki, S.,Harada, M., and Tanimoto, M. (2002) A phase III randomized trial comparing vindesine and cisplatin with or without ifosfamide in patients with advanced non-small-cell lung cancer: long-term follow-up results and analysis of prognostic factors. Lung Cancer, 36, 316-319.
89. Wozniak, A.J. (1999) Single-agent vinorelbine in the treatment of non-small cell lung cancer. Semin Oncol., 26 (62-66), 71-72.
90. Greco, F.A. and Hainsworth, J.D. (1997) Multidisciplinary approach to potentially curable non-small cell carcinoma of the lung. Oncology(Huntingt), 11 (27-36), 41, 49.
91. Baldini, E., Ardizzoni, A., Prochilo, T., Cafferata, M.A., Boni, L., and Tibaldi, C. (2002) Gemcitabine, ifosfamide and navelbine (GIN): a platinum-free combination in advanced non-small-cell lung cancer (NSCLC). Cancer Chemother. Pharmacol., 49, S25-S28.
92. Blajman, C., Balbiani, I., Block, J. et al. (1999) A prospective randomized Phase III trial comparing combination therapy with cyclophosphamide, doxorubicine and 5-fluorouracil with vinorelbine plus doxorubicin in the treatment of advanced breast carcinoma. Cancer, 12, 108-112.
93. Nistico, C., De Matteis, A., Rossi, E. et al. (2005) Primary chemotherapy with epirubicin and vinorelbine in women with locally advanced breast cancer. Anticancer Res., 25 (2B), 1343-1348.
94. Abriel, C., Van Praagh, I., Delue, R. et al. (2005) Pathological and clinical response of a primary chemotherapy regimen combining vinorelbine, epirubicin and paclitaxel as neoadjuvant treatment in patients with operable breast cancer. Oncologist, 10, 242-249.
95. Limetani, S.A., Brufsky, A.M., Erban, J.K. et al. (2006) Phase II study of neoadjuvant docetaxel/vinorelbine followed by surgery and adjuvant doxorubicin/ cyclophosphamide in women with stage II/III breast cancer. Clin. Breast Cancer, 6, 511-517.
96. Wall, M.E., Wani, M.C., Cook, C.E., Palmer, K.H., McPhail, A.T., and Sim, G.A. (1966) Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca accuminata. J. Am. Chem. Soc., 88, 3888-3890.
97. Lorence, A. and Nessler, C.L. (2004) Camptothecin, over four decades of surprising findings. Phytochemistry, 65, 2735-2749.
98. Wani, M.C. and Wall, M.E. (1969) Plant antitumor agents. II. Structure of two new alkaloids from Camptotheca accuminata. J. Org. Chem., 34, 1364-1367.
99. Moertel, C.G., Schutt, A.J., Reitemeier, R.J., and Hahn, R.G. (1972) Phase II study of camptothecin (NSC-100880) in the treatment of gastrointestinal cancer. Cancer Chemother. Rep., 56, 95-102.
100. Gottlieb, J.A. and Luce, J.K. (1972) Treatment of malignant melanoma with camptothecin (NSC-100880) Cancer Chemother Rep., 56, 103.
101. Wani, M.C., Ronman, P.E., Lindley, J.T., and Wall, M.E. (1980) Plant antitumor agents 18. Synthesis and biological activity of camptothecin analogs. J. Med. Chem., 23, 554-560.
102. Wall, M.E. and Wani, M.C. (1994) Camptothecin, in The Monoterpenoid Indole Alkaloids, Supplement to Indoles, Part 4 (ed. J.E. Saxton), Wiley- InterScience, Chichester, pp. 689-713.
103. Kingsbury,W.D., Boehm, J.C., Jakas, D.R., Holden, K.G., Hecht, S.M., Gallagher, G., Caranfa, F.J., McCabe, F.L., Faucette, L.R., Johnson, R.K., andHertzberg, R.P. (1991) Synthesis of water-soluble (aminoalkyl) camptothecin analogs: inhibition of topoisomerase I and antitumor activity. J. Med. Chem., 34, 98-107.
104. Johnson, R.K., Hertzberg, R.P., and Kingsbury,W.D. (1989) Preclinical profile of SK&F 104864, a water soluble analog of camptothecin. Sixth NCI-EORTC Symposium on New Drugs in Cancer Therapy, Abst. 301.
105. Takimoto, C.H. and Arbuck, S.G. (1997) Clinical status and optimal use of topotecan. Oncology (Huntingt), 11, 1635-1646.
106. Sawada, S., Okajima, S., Aiyama, R., Nokata, K., Furuta, T., Yokokura, T., Sugino, E., Yamaguchi, K., and Miyasaka, T. (1991) Synthesis and antitumor activity of 20(S)-camptothecin derivatives: Carbamate-linked, water-soluble derivatives of 7-ethyl-10-hydroxycamptothecin. Chem. Pharm. Bull., 39, 1446-1454.
107. FDA (2000) FDA approves irinotecan as first-line therapy for colorectal cancer. Oncology (Huntingt), 14, 652-654.
108. Wang, X., Zhou, X., and Hecht, S.M. (1999) Role of the 20-hydroxyl group in camptothecin binding by topoisomerase I-DNA binary complex. Biochemistry, 38, 4374-4381.
109. Redinbo, M.R., Stewart, L., Kuhn, P., Champoux, J.J., and Hol, W.G.J. (1998) Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science, 279, 1504-1513.
110. Wall, M.E., Wani, M.C., Nicholas, A.W., Manikumar, G., Tele, C., Moore, L., Truesdale, A., Leitner, P., and Besterman, J.M. (1993) Plant antitumor agents 30. Synthesis and structure activity of novel camptothecin analogs. J. Med. Chem., 36, 2689-2700.
111. Yaegashi, T., Sawada, S., Nagata, H., Furota, T., Yokokura, T., and Miyasaka, T. (1994) Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ringsubstituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives. Chem. Pharm. Bull., 42, 2518-2525.
112. Carrigan, S.W., Fox, P.C., Wall, M.E., Wani, M.C., and Bowen, J.P. (1997) Comparative molecular field analysis and molecular modeling studies of 20-(S)- camptothecin analogs as inhibitors of DNA topoisomerase I and anticancer/ antitumor agents. J. Comput.-Aided Mol. Design, 11, 71-78.
113. Tanizawa, A., Kohn, K.W., Kohlhagen, G., Leteurtre, F., and Pommier, Y. (1995) Differential stabilization of eukaryotic DNA topoisomerase I cleavable complexes by camptothecin derivatives. Biochemistry, 34, 7200-7206.
114. Lavergne, O., Demarquay, D., Bailly, C., Lanco, C., Rolland, A., Huchet, M., Coulomb, H., Muller, N., Baroggi, N., Camara, J., Le Breton, C., Manginot, E., Cazaux, J.-B., and Bigg, D.C.H. (2000) Topoisomerase I-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins. J. Med. Chem., 43, 2285-2289.
115. Ulukan, H. and Swaan, P.W. (2002) Camptothecins. A review of their chemotherapeutic potential. Drugs, 62, 2039-2057.
116. Burris, H.A., Rivkin, S., Reynolds, R., Harris, J., Wax, A., Gerstein, H., Karl, L., Mettinger, K.L., and Staddon, A. (2005) Phase II trial of oral rubitecan in previously treated pancreatic cancer patients. Oncologist, 10, 183-190.
117. Pantazis, P. (1995) The water-insoluble camptothecin analogues: promising drugs for the effective treatment of haematological malignancies. Leuk. Res., 19, 775-788.
118. Emerson, D.L., Bendele, R., Brown, E. et al. (2000) Antitumor efficacy, pharmacokinetics, and biodistributionof NX 211: a low-clearance liposomal formulation of lurtotecan. Clin. Cancer Res., 6, 2903-2912.
119. Jew, S.-S., Kim, H.-J., Kim, M.G., Roh, E.-Y., Hong, C., Kim, J.-K., Lee, J.-H., Lee, H., and Park, H.-G. (1999) Synthesis and in vitro toxicity of hexacyclic camptothecin analogues. Bioorg. Med. Chem. Lett., 9, 3203-3206.
120. Zunino, F. and Pratesi, G. (2004) Camptothecins in clinical development. Exp. Opin. Invest. Drugs, 13, 269-284.
121. Lavergne, O., Harnett, J., Rolland, A., Lanco, C., Lesueur-Ginot, L., Demarquay, D., Huchet, M., Coulomb, H., and Bigg, D.C.H. (1999) BN 80927: a novel camptothecin with inhibitory activities on both topoisomerase I and topoisomerase II. Biorg. Med. Chem. Lett., 9, 2599-2602.
122. Demarquay, D., Huchet, M., Coulomb, H., Leseur-Ginot, L., Lavergne, O., Camara, J., Kasprzik, P.G., Prévost, G., and Bigg, D.H. (2004) BN 80927. A novel homocamptothecin that inhibits proliferation of humantumor cells in vitro and in vivo. Cancer Res., 64, 4942-4949.
123. Verma, R.P. and Hansch, C. (2009) Camptothecins: A SAR/QSAR study. Chem. Rev., 109, 213-235.
124. Li, Q.-Y., Zu, Y.-G., Shi, R.-Z., and Yao, L.-P. (2006) Review camptothecin: current perspectives. Curr. Med. Chem., 13, 2021-2039.
125. Comins, D.L. and Nolan, J.M. (2001) A practical six-step synthesis of (S)- camptothecin. Org Lett., 3, 4255-4257.
126. Liu, L.F. (1983) DNA topoisomerases: enzymes that catalyse the breaking and rejoining of DNA. CRC Crit. Rev. Biochem., 15, 1-24.
127. Eng,W.K.,Pandit, S.D., and Sternglanz, R. (1989) Mapping of the active site tyrosine of eukaryotic DNA topoisomerase I. J. Biol. Chem., 264, 13373-13376.
128. Stewart, L., Redinbo, M.R., Qiu, X. et al. (1998) A model for the mechanism of human topoisomerase I. Science, 279, 1534-1541.
129. Kjeldsen, E., Svejstrup, J.Q., Gromova, I.I. et al. (1992) Camptothecin inhibits both the cleavage and religation reactions of eukaryotic DNA topoisomerase I. J. Mol. Biol., 228, 1025-1030.
130. Hsiang, Y.H., Lihou, M.G., and Liu, L.F. (1989) Arrest of replication forks by drugstabilized topoisomerase I-DNAcleavable complexes as a mechanism of cell killing by camptothecin. Cancer Res., 49, 5077-5082.
131. Staker, B.L., Hjerrild, K., Feese, M.D., Behnke, C.A., Burgin, A.B., and Stewart, L. (2002) The mechanism of topoisomerase I poisoning by a camptothecin analog. Proc. Natl. Sci. USA, 99, 15387-15392.
132. Staker, B.L., Feese, M.D., Cushman, M., Pommier, Y., Zembower, D., Stewart, L., and Burgin, A.B. (2005) Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex. J. Med. Chem., 48, 2336-2345.
133. Potmesil, M. (1994)Camptothecins: from bench research to hospital wards. Cancer Res., 54, 1431-1439.
134. Mathijssen, R.H., van Alphen, R.J., Verweij, J., Loos, W.J., Nooter, K., Stoter, G., and Sparreboom, A. (2001) Clinical pharmacokinetics and metabolism of irinotecan (CPT-11). Clin. Cancer. Res., 7, 2182-2194.
135. Takasuna, K.,Hagiwara,T.,Hirohashi, M. et al. (1996) Involvement of betaglucuronidase in intestinal microflora in the intestinal toxicity of the antitumor camptothecin derivative irinotecan hydrochloride (CPT-11) in rats. Cancer Res., 56, 3752-3757.
136. Negoro, S., Fukuoka, M.,Masuda, N. et al. (1991)Phase I study of weekly intravenous infusions of CPT-11, a new derivative of camptothecin, in the treatment of advanced non-small-cell lung cancer. J. Natl. Cancer Inst., 83, 1164-1168.
137. Costin, D. and Potmesil, M. (1994) Preclinical and clinical development of camptothecins. Adv. Pharmacol., 29B, 51-72.
138. Meng, L.-H., Liao, Z.-Y., and Pommier, Y. (2003) Non-camptothecin DNA topoisomerase I inhibitors in cancer therapy. Curr. Top. Med. Chem., 3, 305-320.
139. Chrencik, J.E., Staker, B.L., Burgin, A.B., Pourquier, P., Pommier, Y., Stewart, L., and Redinbo, M.L. (2004)Mechanisms of camptothecin resistance by humantopoisomerase I mutations. J. Mol. Biol., 339, 773-784.
140. Xu, Y. and Villalona-Calero, M.A. (2002) Irinotecan: mechanisms of tumor resistance and novel strategies for modulating its activity. Ann. Oncol., 13, 1841-1851.
141. Langer, C.J. (2001) The emerging role of irinotecan in lung cancer. Oncology (Huntingt), 15, 15-21.
142. Negoro, S., Masuda, N., Takada, Y., Sugiura, T., Kudoh, S., Katakami, N., Arioshi, Y., Ohashi, Y., Niitani, H., and Fukuoka, M. (2003) Randomised phase III trial of irinotecan combined with cisplatin for advanced non-small-cell lung cancer. Br. J. Cancer, 88, 335-341.
143. Gauvin, A., Bressolle, F., Martineau, P., Astre, C., and Pinguet, F. (2002) In vitro schedule-dependent interaction between irinotecan and vinorelbine in NCI H460 non-small cell lung cancer line. Anticancer Res., 22, 905-912.
144. Charasson, V., Haaz, M.C., and Robert, J. (2002) Determination of drug interactions occurring with the metabolic pathways of irinotecan. Drug Metab. Dispos., 30, 731-733.
145. Saltz, L.B., Douillard, J.Y., Pirotta, N., Alakl, M., Gruia, G., Awad, L., Elfring, G.L., Locker, P.K., and Miller, L.L. (2001) Irinotecan plus fluorouracil/leucovorin for metastatic colorectal cancer: a new survival standard. Oncologist, 6, 81-89.
146. Tamura, T. (2001) New state of the art in small-cell lung cancer. Oncology (Huntingt), 15, 8-10.
147. Lara, P.N., Jr., Natale, R., Crowley, J., Lenz, H.J., Redman, M.W.,Carleton, J.E., Jett, J., Langer, C.J., Kuebler, P., Dakhi, S.R., Chansky, K., and Gandara, D.R. (2009) Phase III trial of irinotecan/cisplatin compared with etoposide/cisplatin in extensive-stage small-cell lung cancer: clinical and pharmacogenomic results from SWOG S0124. J. Clin. Oncol., 27, 2530-2535.
148. Jagasia, M.N., Langer, C.J., Johnson, D.H., Yunus, F., Rodgers, J.S., Schlabach, L.L., Cohen, A.G., Shyr, Y., Carbone, D.P., and Devore, R.F. (2001) Weekly irinotecan and cisplatin in advanced nonsmall cell lung cancer: a multicenter phase II study. Clin. Cancer Res., 7, 68-73.
149. Carmichel, J., Gordon, A., Malfetano, J. et al. (1996) Topotecan, a new active drug, vs paclitaxel in advanced epithelial ovarian carcinoma: International Topotecan Study Group Trial. Proc. Am. Soc. Clin. Oncol., 15, Abst. 765.
150. Herzog, T.J. (2002) Update on role of topotecan in the treatment of recurrent ovarian cancer. Oncologist, 7 (Suppl.5), 3-10.
151. Sehouli, J., Sttengel, D., Oskay, G., Camara, O., Hindenburg, H.J., Klare, P., Blohmer, J., Heinrich, G., Elling, D., Ledwon, P., and Lichtenegger, W. (2002) A phase II study of topotecan plus gemcitabine in the treatment of patients with relapsed ovarian cancer after failure of first-line therapy. Ann. Oncol., 13, 1749-1755.