The long story of camptothecin: From traditional medicine to drugs
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Wall, 1966, Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata, J Am Chem Soc, 88, 3888, 10.1021/ja00968a057
Gottlieb, 1970, Preliminary pharmacologic and clinical evaluation of camptothecin sodium (NSC-100880), Cancer Chemother Rep, 54, 461
Gottlieb, 1972, Treatment of malignant melanoma with camptothecin (NSC-100880), Cancer Chemother Rep, 56, 103
Moertel, 1972, Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer, Cancer Chemother Rep, 56, 95
Muggia, 1972, Phase I clinical trial of weekly and daily treatment with camptothecin (NSC-100880): correlation with preclinical studies, Cancer Chemother Rep, 56, 515
Hsiang, 1985, Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I, J Biol Chem., 260, 14873, 10.1016/S0021-9258(17)38654-4
Thomsen, 1987, Sequence specificity of DNA topoisomerase I in the presence and absence of camptothecin, EMBO J, 6, 1817, 10.1002/j.1460-2075.1987.tb02436.x
Pommier, 1987, DNA unwinding and inhibition of mouse leukemia L1210 DNA topoisomerase I by intercalators, Nucl Acids Res, 15, 6713, 10.1093/nar/15.16.6713
Jaxel, 1988, Topoisomerase I interactions with SV40 DNA in the presence and absence of camptothecin, Nucl Acids Res, 16, 11157, 10.1093/nar/16.23.11157
Kjeldsen, 1988, Sequence-dependent effect of camptothecin on human topoisomerase I DNA cleavage, J Mol Biol, 202, 333, 10.1016/0022-2836(88)90462-7
Jaxel, 1989, Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for site specific receptor site and a relation to antitumor activity, Cancer Res, 49, 1465
Hsiang, 1988, Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin, Cancer Res, 48, 1722
Kulkarni, 2010, Production of camptothecin in cultures of Chonemorpha grandiflora, Pharm Res, 2, 296
Fulzele, 2005, Comparison of techniques for the extraction of the anti-cancer drug camptothecin from Nothapodytes foetida, J Chromatogr A, 1063, 9, 10.1016/j.chroma.2004.11.020
Shi, 2009, Homogenate extraction technology of camptothecine and hydroxycamptothecin from Camptotheca acuminata leaves, J Forestry Res, 20, 168, 10.1007/s11676-009-0030-2
Zeng, 2013, New and highly efficient column chromatographic extraction and simple purification of camptothecin from Camptotheca acuminata and Nothapodytes pittosporoides, Phytochem Anal., 24, 623, 10.1002/pca.2441
Upadhya, 2014, Compound specific extraction of camptothecin from nothapodytes nimmoniana and piperine from piper nigrum using accelerated solvent extractor, J Anal Chem
Consideration of Proposals for Amendment Of Appendices II www.cites.org/eng/cop/11/prop/58.pdf. accessed 30 July 2016.
Venditto, 2010, Cancer therapies utilizing the camptothecins: a review of in vivo literature, Mol Pharm, 7, 307, 10.1021/mp900243b
Adams, 2005
Hertzberg, 1989, On the mechanism of topoisomerase I inhibition by camptothecin: evidence for binding to an enzyme-DNA complex, Biochemistry, 28, 4629, 10.1021/bi00437a018
Pommier, 2006, Topoisomerase I inhibitors: camptothecins and beyond, Nat Rev Cancer, 6, 789, 10.1038/nrc1977
Ulukan, 2002, Camptothecins a review of their chemotherapeutic potential, Drugs, 62, 2039, 10.2165/00003495-200262140-00004
Wang, 1990, The role of DNA topoisomerases in recombination and genome stability: a double-edged sword?, Cell, 62, 403, 10.1016/0092-8674(90)90002-V
Stewart, 1998, A model for the mechanism of human topoisomerase I, Science, 279, 1534, 10.1126/science.279.5356.1534
Redinbo, 1998, Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA, Science, 279, 1504, 10.1126/science.279.5356.1504
Dancey, 1996, Current perspectives on camptothecins in cancer treatment, Br J Cancer, 74, 327, 10.1038/bjc.1996.362
Pommier, 1995, Interaction of an alkylating camptothecin derivative with a DNA base at topoisomerase I-DNA cleavage sites, Proc Natl Acad Sci U S A, 92, 8861, 10.1073/pnas.92.19.8861
Shen, 1993, Concise total synthesis of dl-Camptothecin and related anticancer drugs, J Org Chem, 58, 611, 10.1021/jo00055a012
Comins, 2001, A pratical six-step synthesis of (S)-camptothecin, Org Lett, 3, 4255, 10.1021/ol0169271
Wall, 1995, 21
Crow, 1992, Structural modifications of camptothecin and effects on topoisomerase I inhibition, J Med Chem, 35, 4160, 10.1021/jm00100a022
Wani, 1980, Plant antitumor agents. Synthesis and biological activity of camptothecin analogues, J Med Chem, 23, 554, 10.1021/jm00179a016
Nicholas, 1990, Plant antitumor agents. Synthesis and biological activity of ring D and ring E modified analogues of camptothecin, J Med Chem, 33, 972, 10.1021/jm00165a014
Rowinsky, 1992, Phase I and pharmacologic study of topotecan: a novel topoisomerase I inhibitor, J Clin Oncol, 10, 647, 10.1200/JCO.1992.10.4.647
Wani, 1987, Plant antitumor agents. Resolution of a key tricyclic synthon, 5′(RS)-1,5-dioxo-5′-ethyl-5′-hydroxy-2′H,5′H,6′H-6′-oxopyrano[3′,4′-f]delta 6,8-tetrahydro-indolizine: total synthesis and antitumor activity of 20(S)- and 20(R)-camptothecin, J Med Chem, 30, 2317, 10.1021/jm00395a024
Wang, 1997, Recent advances in the discovery and development of topoisomerase inhibitors as antitumor agents, Med Res Rev, 17, 367, 10.1002/(SICI)1098-1128(199707)17:4<367::AID-MED3>3.0.CO;2-U
Sawada, 1996, Synthesis of CPT-11 (irinotecan hydrochloride trihydrate), Ann N Y Acad Sci, 803, 13, 10.1111/j.1749-6632.1996.tb26372.x
Simon, 2000, Differential toxicities of anticancer agents among DNA repair and checkpoint mutants of saccharomyces cerevisiae, Cancer Res, 60, 328
Kingsbury, 1991, Synthesis of water-soluble (aminoalky1)camptothecin analogues: inhibition of topoisomerase I and antitumor activity, J Med Chem, 34, 98, 10.1021/jm00105a017
Wall, 1993, Plant antitumor agents. Synthesis and structure activity of novel camptothecin analogs, J Med Chem, 36, 2689, 10.1021/jm00070a013
Takimoto, 1998, Clinical applications of the camptothecins, Biochim Biophys Acta, 1400, 107, 10.1016/S0167-4781(98)00130-4
Jelovac, 2011, Recent progress in the diagnosis and treatment of ovarian cancer, Cancer J Clin, 61, 183, 10.3322/caac.20113
Kudoh, 1998, Phase II study of irinotecan combined with cisplatin in patients with previously untreated small cell lung cancer, J Clin Oncol, 16, 1068, 10.1200/JCO.1998.16.3.1068
Von Pawel, 1999, Topotecan versus cyclophosphamide, doxorubicin, and vincristine for the treatment of recurrent small-cell lung cancer, J Clin Oncol, 17, 658, 10.1200/JCO.1999.17.2.658
Dong, 2003, E2F-1 overexpression sensitizes colorectal cancer cells to camptothecin, J Cancer Gene Cell Ther, 10, 168, 10.1038/sj.cgt.7700565
Zarogoulidis, 2009, Topotecan–carboplatin–etoposide combination as 1st line treatment in patients with small cell lung cancer, J Lung Cancer, 66, 226, 10.1016/j.lungcan.2009.02.003
Emerson, 1995, In vivo antitumor activity of two new seven-substituted water-soluble camptothecin analogues, Cancer Res, 55, 603
Besterman, 1996, Topoisomerase I inhibition by the camptothecin analog Gl147211C: from the laboratory to the clinic, Ann NY Acad Sci, 803, 202, 10.1111/j.1749-6632.1996.tb26389.x
Kunimoto, 1987, Antitumor activity of 7-ethyl-10-[4-(1- piperidino)- I -piperidino]carbonyloxy-camptothecin, a novel water-soluble derivative of camptothecin, against murine tumors, Cancer Res, 47, 5944
Kawato, 1991, Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT- 11, in the antitumor effect of CPT- 11, Cancer Res, 51, 4187
Kawato, 1991, Antitumor activity of a camptothecin derivative, CPT- 1, against human tumor xeno grafts in nude mice, Cancer Chemother Pharmacol, 28, 192, 10.1007/BF00685508
Kawato, 1993, Inhibitory activity of camptothecin derivatives against acetylcholinesterase in dogs and their binding activity to acetylcholine receptors in rats, J Pharm Pharmacol, 45, 444, 10.1111/j.2042-7158.1993.tb05573.x
Taguchi, 1990, Phase I clinical study of CPT-1. Research group of CPT-1, Gan to Kagaku Ryoho, 17, 115
Rowinsky, 1994, Phase I and pharmacological study of the novel topoisomerase I inhibitor 7-ethyl-10-[4-(1-piperidino)-l -piperidino] carbonyloxycamptothecin (CPT-1) administered as a ninetyminute infusion every 3 weeks, Cancer Res, 54, 427
Mathijsen, 2002, Pharmacology of topoisomerase I inhibitors irinotecan (CPT-11) and topotecan, Curr Cancer Drug Targ, 2, 103, 10.2174/1568009023333890
Murphy, 1992, Granulocytecolony stimulating factor (G-CSF) does not increase the maximum tolerated dose (MTD) in a phase I study of topotecan, Proc Am Soc Clin Oncol, 11, 139
Janik, 1993, Prechemotherapy granulocyte-macrophage colony stimulating factor (GM-CSF) prevents topotecan-induced neutropenia, Proc Am Soc Clin Oncol, 12, 437
Xia, 2013, Identification of repurposed small molecule drugs for chordoma therapy, Cancer Biol Ther, 14, 638, 10.4161/cbt.24596
Burris, 2005, Phase II trial of oral rubitecan in previously treated pancreatic cancer patients, Oncologist, 10, 183, 10.1634/theoncologist.10-3-183
Beretta, 2013, Camptothecin resistance in cancer: insights into the molecular mechanisms of a DNA-damaging drug, Curr Med Chem, 20, 1541, 10.2174/0929867311320120006
Pratesi, 2004, Zunino F Gimatecan, A novel Camptothecin with a promising preclinical profile, Anticancer Drugs, 15, 545, 10.1097/01.cad.0000131687.08175.14
Beretta, 2012, Namitecan: a hydrophilic camptothecin with a promising preclinical profile, Curr Med Chem, 19, 3488, 10.2174/092986712801323252
Liehr, 2000, Pharmacology of camptothecin esters, Ann N Y Acad Sci, 922, 216, 10.1111/j.1749-6632.2000.tb07040.x
Xie, 2016, Synthesis, characterization, and evaluation of mPEG–SN38 and mPEG–PLA–SN38 micelles for cancer therapy, Int J Nanomed, 11, 1677
Ko, 2016, Nanomedicine developments in the treatment of metastatic pancreatic cancer: focus on nanoliposomal irinotecan, Int J Nanomed, 11, 1225, 10.2147/IJN.S88084
Lin, 2016, Preclinical effects of CRLX101, an investigational camptothecin-containing nanoparticle drug conjugate, on treating glioblastoma multiforme via apoptosis and antiangiogenesis, Oncotarget, 7, 42408, 10.18632/oncotarget.9878
Chen, 2005, Phase I and pharmacokinetic study of Bay 38–3441, a camptothecin glycoconjugate, administered as a 30-minute infusion daily for five days every 3 weeks in patients with advanced solid malignancies, Invest New Drugs, 23, 455, 10.1007/s10637-005-2905-1
Homsi, 2007, Phase I trial of poly-L-glutamate camptothecin (CT-2106) administered weekly in patients with advanced solid malignancies, Clin Cancer Res, 13, 5855, 10.1158/1078-0432.CCR-06-2821