Progress on microtubulin-site vascular disruption agents

LI Wei; ZHOU Feng; ZHENG Can-hui; ZHOU You-jun

doi:10.3969/j.issn.1006-0111.2013.06.001

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Volume 31 Issue 6

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2013 > 31(6): 401-404,423

LI Wei, ZHOU Feng, ZHENG Can-hui, ZHOU You-jun. Progress on microtubulin-site vascular disruption agents[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 401-404,423. doi: 10.3969/j.issn.1006-0111.2013.06.001

Citation:

LI Wei, ZHOU Feng, ZHENG Can-hui, ZHOU You-jun. Progress on microtubulin-site vascular disruption agents[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 401-404,423. doi: 10.3969/j.issn.1006-0111.2013.06.001

Progress on microtubulin-site vascular disruption agents

doi: 10.3969/j.issn.1006-0111.2013.06.001

Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2012-10-07
Rev Recd Date: 2013-04-01

Abstract

Vascular disrupting agents (VDAs) are a novel class of the antitumor agents that selectively damage the established tumor vessel. This kind of agents can selectively damage the tumor vascular, which apply adequate oxygen and nutrient for tumor growth and metabolism, and result in the tumor cell necrosis. In recent years, a number of VDAs that interact with microtubule had been involved in clinical trials, and showed good prospects for development and application, which were summarized in this paper.
- microtubulin,
- vascular disrupting agents (VDAs),
- anticancer,

References

[1]	Jemal A, Bray F, Center MM, et al. Global cancer statistics[J]. Cancer J Clin, 2011, 61(2):69.
[2]	He X, Li S, Huang H, et al. A pharmacokinetic and safety study of single dose intravenous combretastatin A4 phosphate in Chinese patients with refractory solid tumours[J]. Br J Clin Pharmacol, 2011, 71(6):860.
[3]	Tozer GM, Kanthou C, Baguley BC. Disrupting tumour blood vessels[J]. Nat Rev Cancer, 2005, 5(6):423.
[4]	Pettit GR, Temple C Jr, Narayanan VL, et al. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs[J]. Anticancer Drug Des, 1995, 10(4):299.
[5]	Ding XQ, Zhang ZQ, Li S, et al. Combretastatin A-4 phosphate induces programmed cell death in vascular endothelial cells[J]. Oncol Res, 2011, 19(7):303.
[6]	Nathan P, Zweifel M, Padhani AR, et al. Phase I trial of combretastatin A4 phosphate (CA4P) in combination with bevacizumab in patients with advanced cancer[J]. Clin Cancer Res, 2012, 18(12):3428.
[7]	Delmonte A, Sessa C. AVE8062:a new combretastatin derivative vascular disrupting agent[J]. Expert Opin Invest Drugs, 2009, 18(10):1541.
[8]	Hori K. Antineoplastic strategy:irreversible tumor blood flow stasis induced by the combretastatin A-4 derivative AVE8062 (AC7700)[J]. Chemotherapy, 2005, 51(6):357.
[9]	Nihei Y, Suga Y, Morinaga Y, et al. A novel combretastatin A-4 derivative, AC-7700, shows marked antitumor activity against advanced solid tumors and orthotopically transplanted tumors[J]. Jpn J Cancer Res, 1999, 90(9):1016.
[10]	Clémenson C, Jouannot E, Merino-Trigo A, et al. The vascular disrupting agent ombrabulin (AVE8062) enhances the efficacy of standard therapies in head and neck squamous cell carcinoma xenograft models[J]. Invest New Drugs, 2013, 31(2):273.
[11]	Sessa C, Soria JC, Tolcher A, et al. A phase I pharmacokinetic and pharmacodynamic study of AVE8062, a novel vascular disrupting agent, in patients (PTS) with advanced solid tumors-preliminary results[J]. Ann Oncol, 2009, 20:24.
[12]	Morinaga Y, Suga Y, Ehara S, et al. Combination effect of AC-7700, a novel combretastatin A-4 derivative, and cisplatin against murine and human tumors in vivo[J]. Cancer Sci, 2003, 94(2):200.
[13]	Salmon HW, Siemann DW. Effect of the second-generation vascular disrupting agent OXi4503 on tumor vascularity[J]. Clin Cancer Res, 2006, 12(13):4090.
[14]	Rice L, Pampo C, Lepler S, et al. Support of a free radical mechanism for enhanced antitumor efficacy of the microtubule disruptor OXi4503[J]. Microvasc Res, 2011, 81(1):44.
[15]	Folkes LK, Christlieb M, Madej E, et al. Oxidative metabolism of combretastatin A-1 producesquinone intermediates with the potential to bind to nucleophiles and to enhance oxidative stress via free radicals[J]. Chem Res Toxicol, 2007, 20(12):1885.
[16]	Sheng Y, Hua J, Pinney KG, et al. Combretastatin family member OXI4503 induces tumor vascular collapse through the induction of endothelial apoptosis[J]. Int J Cancer, 2004, 111(4):604.
[17]	Cummings J, Zweifel M, Smith N, et al. Evaluation of cell death mechanisms induced by the vascular disrupting agent OXi4503 during a phase I clinical trial[J]. Br J Cancer, 2012, 106(11):1766.
[18]	Wankhede M, Dedeugd C, Siemann DW, et al. In vivo functional differences in microvascular response of 4T1 and Caki-1 tumors after treatment with OXi4503[J]. Oncol Rep, 2010, 23(3):685.
[19]	Mckeage MJ, Baguley BC. Disrupting established tumor blood vessels:an emerging therapeutic strategy for cancer[J]. Cancer, 2010, 116(8):1859.
[20]	Patterson DM, Zweifel M, Middleton MR, et al. Phase I clinical and pharmacokinetic evaluation of the vascular-disrupting agent OXi4503 in patients with advanced solid tumors[J]. Clin Cancer Res, 2012, 18(5):1415.
[21]	Madlambayan GJ, Meacham AM, Hosaka K, et al. Leukemia regression by vascular disruption and antiangiogenic therapy[J]. Blood, 2010, 116(9):1539.
[22]	Flynn BL, Gill GS, Grobelny DW, et al. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties[J]. J Med Chem, 2011, 54(17):6014.
[23]	Kremmidiotis G, Leske AF, Lavranos TC, et al. BNC105:a novel tubulin polymerization inhibitor that selectively disrupts tumor vasculature and displays single-agent antitumor efficacy[J]. Mol Cancer Ther, 2010, 9(6):1562.
[24]	Rischin D, Bibby DC, Chong G, et al. Clinical, pharmacodynamic, and pharmacokinetic evaluation of BNC105P:a phase I trial of a novel vascular disrupting agent and inhibitor of cancer cell proliferation[J]. Clin Cancer Res, 2011, 17(15):5152.
[25]	Sirisoma N, Kasibhatla S, Pervin A, et al. Discovery of 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (EP128265, MPI-0441138) as a potent inducer of apoptosis with high in vivo activity[J]. J Med Chem, 2008, 51(15):4771.
[26]	Sirisoma N, Pervin A, Zhang H, et al. Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration[J]. J Med Chem, 2009, 52(8):2341.
[27]	Kasibhatla S, Baichwal V, Cai SX, et al. MPC-6827:a small-molecule inhibitor of microtubuleformation that is not a substrate for multidrug resistance pumps[J]. Cancer Res, 2007, 67(12):5865.
[28]	Tsimberidou AM, Akerley W, Schabel MC, et al. Phase I clinical trial of MPC-6827(Azixa), a microtubule destabilizing agent, in patients with advanced cancer[J]. Mol Cancer Ther, 2010, 9(12):3410.
[29]	Kemnitzer W, Drewe J, Jiang S, et al. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the 4-aryl group[J]. J Med Chem, 2004, 47(25):6299.
[30]	Kemnitzer W, Kasibhatla S, Jiang S, et al. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure-activity relationships of the 7-and 5-, 6-, 8-positions[J]. Bioorg Med Chem Lett, 2005, 15(21):4745.
[31]	Read WL, Rosen P, Lee P, et al. Pharmacokinetic and pharmacodynamic results of a 4-hr iv administration phase I study with EPC2407, a novel vascular disrupting agent[J]. J Clin Oncol,2009, 27(15Suppl):3569.
[32]	Fox E, Maris JM, Widemann BC, et al. A phase I study of ABT-751, an orally bioavailable tubulin inhibitor, administered daily for 21 days every 28 days in pediatric patients with solid tumors[J]. Clin Cancer Res, 2008, 14(4):1111.
[33]	Burns CJ, Fantino E, Phillips ID, et al. CYT997:a novel orally active tubulin polymerization inhibitor with potent cytotoxic and vascular disrupting activity in vitro and in vivo[J]. Mol Cancer Ther, 2009, 8(11):3036.
[34]	Burge M, Francesconi A, Kotasek D, et al. Phase I, pharmacokinetic and pharmacodynamic evaluation of CYT997, an orally-bioavailable cytotoxic and vascular-disrupting agent[J]. Invest New Drugs, 2012, 31(1):126.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Progress on microtubulin-site vascular disruption agents

Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2012-10-07

Rev Recd Date: 2013-04-01

Key words:

Abstract: Vascular disrupting agents (VDAs) are a novel class of the antitumor agents that selectively damage the established tumor vessel. This kind of agents can selectively damage the tumor vascular, which apply adequate oxygen and nutrient for tumor growth and metabolism, and result in the tumor cell necrosis. In recent years, a number of VDAs that interact with microtubule had been involved in clinical trials, and showed good prospects for development and application, which were summarized in this paper.

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Reference (34)

[1]	Jemal A, Bray F, Center MM, et al. Global cancer statistics[J]. Cancer J Clin, 2011, 61(2):69.
[2]	He X, Li S, Huang H, et al. A pharmacokinetic and safety study of single dose intravenous combretastatin A4 phosphate in Chinese patients with refractory solid tumours[J]. Br J Clin Pharmacol, 2011, 71(6):860.
[3]	Tozer GM, Kanthou C, Baguley BC. Disrupting tumour blood vessels[J]. Nat Rev Cancer, 2005, 5(6):423.
[4]	Pettit GR, Temple C Jr, Narayanan VL, et al. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs[J]. Anticancer Drug Des, 1995, 10(4):299.
[5]	Ding XQ, Zhang ZQ, Li S, et al. Combretastatin A-4 phosphate induces programmed cell death in vascular endothelial cells[J]. Oncol Res, 2011, 19(7):303.
[6]	Nathan P, Zweifel M, Padhani AR, et al. Phase I trial of combretastatin A4 phosphate (CA4P) in combination with bevacizumab in patients with advanced cancer[J]. Clin Cancer Res, 2012, 18(12):3428.
[7]	Delmonte A, Sessa C. AVE8062:a new combretastatin derivative vascular disrupting agent[J]. Expert Opin Invest Drugs, 2009, 18(10):1541.
[8]	Hori K. Antineoplastic strategy:irreversible tumor blood flow stasis induced by the combretastatin A-4 derivative AVE8062 (AC7700)[J]. Chemotherapy, 2005, 51(6):357.
[9]	Nihei Y, Suga Y, Morinaga Y, et al. A novel combretastatin A-4 derivative, AC-7700, shows marked antitumor activity against advanced solid tumors and orthotopically transplanted tumors[J]. Jpn J Cancer Res, 1999, 90(9):1016.
[10]	Clémenson C, Jouannot E, Merino-Trigo A, et al. The vascular disrupting agent ombrabulin (AVE8062) enhances the efficacy of standard therapies in head and neck squamous cell carcinoma xenograft models[J]. Invest New Drugs, 2013, 31(2):273.
[11]	Sessa C, Soria JC, Tolcher A, et al. A phase I pharmacokinetic and pharmacodynamic study of AVE8062, a novel vascular disrupting agent, in patients (PTS) with advanced solid tumors-preliminary results[J]. Ann Oncol, 2009, 20:24.
[12]	Morinaga Y, Suga Y, Ehara S, et al. Combination effect of AC-7700, a novel combretastatin A-4 derivative, and cisplatin against murine and human tumors in vivo[J]. Cancer Sci, 2003, 94(2):200.
[13]	Salmon HW, Siemann DW. Effect of the second-generation vascular disrupting agent OXi4503 on tumor vascularity[J]. Clin Cancer Res, 2006, 12(13):4090.
[14]	Rice L, Pampo C, Lepler S, et al. Support of a free radical mechanism for enhanced antitumor efficacy of the microtubule disruptor OXi4503[J]. Microvasc Res, 2011, 81(1):44.
[15]	Folkes LK, Christlieb M, Madej E, et al. Oxidative metabolism of combretastatin A-1 producesquinone intermediates with the potential to bind to nucleophiles and to enhance oxidative stress via free radicals[J]. Chem Res Toxicol, 2007, 20(12):1885.
[16]	Sheng Y, Hua J, Pinney KG, et al. Combretastatin family member OXI4503 induces tumor vascular collapse through the induction of endothelial apoptosis[J]. Int J Cancer, 2004, 111(4):604.
[17]	Cummings J, Zweifel M, Smith N, et al. Evaluation of cell death mechanisms induced by the vascular disrupting agent OXi4503 during a phase I clinical trial[J]. Br J Cancer, 2012, 106(11):1766.
[18]	Wankhede M, Dedeugd C, Siemann DW, et al. In vivo functional differences in microvascular response of 4T1 and Caki-1 tumors after treatment with OXi4503[J]. Oncol Rep, 2010, 23(3):685.
[19]	Mckeage MJ, Baguley BC. Disrupting established tumor blood vessels:an emerging therapeutic strategy for cancer[J]. Cancer, 2010, 116(8):1859.
[20]	Patterson DM, Zweifel M, Middleton MR, et al. Phase I clinical and pharmacokinetic evaluation of the vascular-disrupting agent OXi4503 in patients with advanced solid tumors[J]. Clin Cancer Res, 2012, 18(5):1415.
[21]	Madlambayan GJ, Meacham AM, Hosaka K, et al. Leukemia regression by vascular disruption and antiangiogenic therapy[J]. Blood, 2010, 116(9):1539.
[22]	Flynn BL, Gill GS, Grobelny DW, et al. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties[J]. J Med Chem, 2011, 54(17):6014.
[23]	Kremmidiotis G, Leske AF, Lavranos TC, et al. BNC105:a novel tubulin polymerization inhibitor that selectively disrupts tumor vasculature and displays single-agent antitumor efficacy[J]. Mol Cancer Ther, 2010, 9(6):1562.
[24]	Rischin D, Bibby DC, Chong G, et al. Clinical, pharmacodynamic, and pharmacokinetic evaluation of BNC105P:a phase I trial of a novel vascular disrupting agent and inhibitor of cancer cell proliferation[J]. Clin Cancer Res, 2011, 17(15):5152.
[25]	Sirisoma N, Kasibhatla S, Pervin A, et al. Discovery of 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (EP128265, MPI-0441138) as a potent inducer of apoptosis with high in vivo activity[J]. J Med Chem, 2008, 51(15):4771.
[26]	Sirisoma N, Pervin A, Zhang H, et al. Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration[J]. J Med Chem, 2009, 52(8):2341.
[27]	Kasibhatla S, Baichwal V, Cai SX, et al. MPC-6827:a small-molecule inhibitor of microtubuleformation that is not a substrate for multidrug resistance pumps[J]. Cancer Res, 2007, 67(12):5865.
[28]	Tsimberidou AM, Akerley W, Schabel MC, et al. Phase I clinical trial of MPC-6827(Azixa), a microtubule destabilizing agent, in patients with advanced cancer[J]. Mol Cancer Ther, 2010, 9(12):3410.
[29]	Kemnitzer W, Drewe J, Jiang S, et al. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the 4-aryl group[J]. J Med Chem, 2004, 47(25):6299.
[30]	Kemnitzer W, Kasibhatla S, Jiang S, et al. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure-activity relationships of the 7-and 5-, 6-, 8-positions[J]. Bioorg Med Chem Lett, 2005, 15(21):4745.
[31]	Read WL, Rosen P, Lee P, et al. Pharmacokinetic and pharmacodynamic results of a 4-hr iv administration phase I study with EPC2407, a novel vascular disrupting agent[J]. J Clin Oncol,2009, 27(15Suppl):3569.
[32]	Fox E, Maris JM, Widemann BC, et al. A phase I study of ABT-751, an orally bioavailable tubulin inhibitor, administered daily for 21 days every 28 days in pediatric patients with solid tumors[J]. Clin Cancer Res, 2008, 14(4):1111.
[33]	Burns CJ, Fantino E, Phillips ID, et al. CYT997:a novel orally active tubulin polymerization inhibitor with potent cytotoxic and vascular disrupting activity in vitro and in vivo[J]. Mol Cancer Ther, 2009, 8(11):3036.
[34]	Burge M, Francesconi A, Kotasek D, et al. Phase I, pharmacokinetic and pharmacodynamic evaluation of CYT997, an orally-bioavailable cytotoxic and vascular-disrupting agent[J]. Invest New Drugs, 2012, 31(1):126.

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Progress on microtubulin-site vascular disruption agents

doi: 10.3969/j.issn.1006-0111.2013.06.001

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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