Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers

SHI Saijian; ZHANG Wen; LI Tingyou; ZHUANG Chunlin

doi:10.3969/j.issn.1006-0111.2017.05.001

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2017 > 35(5): 385-393,397

SHI Saijian, ZHANG Wen, LI Tingyou, ZHUANG Chunlin. Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(5): 385-393,397. doi: 10.3969/j.issn.1006-0111.2017.05.001

Citation:

SHI Saijian, ZHANG Wen, LI Tingyou, ZHUANG Chunlin. Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(5): 385-393,397. doi: 10.3969/j.issn.1006-0111.2017.05.001

Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers

doi: 10.3969/j.issn.1006-0111.2017.05.001

1.
Department of Medicinal Chemistry, School of Pharmacy, Nanjing Medical University, Nanjing 211166, China
2.
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2017-05-03
Rev Recd Date: 2017-06-19

Abstract

In 2015, more than 8 million people died from various kinds of cancers all over the world. Although traditional chemotherapeutic drugs are widely used in clinic, more than 50% of cancers are significantly resistant to traditional chemotherapeutic drugs. Tubulin targeting agents have been confirmed to be effective anti-cancer drugs in clinic. However, some anti-microtubule agents developed resistance after long-term use, such as paclitaxel and vinblastine. In recent years, it is reported that tubulin modulators targeting on the colchicine-binding site are extremely effective against multi-drug resistant cancer cells. In this article, different anti-microtubule agents targeting multi-drug resistant cancers are reviewed.
- anti-cancer,
- multidrug resistant,
- tubulin,
- modulator

References

[1]	Parker AL,Kavallaris M,McCarroll JA.Microtubules and their role in cellular stress in cancer［J］.Front Oncol,2014,4:153.
[2]	Prosser SL,Pelletier L.Mitotic spindle assembly in animal cells: a fine balancing act［J］.Nat Rev Mol Cell Biol,2017,18(3):187-201.
[3]	Jordan MA,Wilson L.Microtubules as a target for anticancer drugs［J］.Nat Rev Cancer,2004,4(4):253-265.
[4]	Li W,Zhang H,Assaraf YG,et al.Overcoming ABC transporter-mediated multidrug resistance: Molecular mechanisms and novel therapeutic drug strategies［J］.Drug Resist Updat,2016,27:14-29.
[5]	Krishna R,Mayer LD.Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs［J］.Eur J Pharm Sci,2000,11(4):265-283.
[6]	Hao XY,Widersten M,Ridderstrom M,et al.Co-variation of glutathione transferase expression and cytostatic drug resistance in HeLa cells: establishment of class Mu glutathione transferase M3-3 as the dominating isoenzyme［J］.Biochem J,1994,297 (Pt 1):59-67.
[7]	Ogiso Y,Tomida A,Tsuruo T.Nuclear localization of proteasomes participates in stress-inducible resistance of solid tumor cells to topoisomerase Ⅱ-directed drugs［J］.Cancer Res,2002,62(17):5008-5012.
[8]	Fernald K,Kurokawa M.Evading apoptosis in cancer［J］.Trends Cell Biol,2013,23(12):620-633.
[9]	Krauze A,Grinberga S,Krasnova L,et al.Thieno[2,3-b]pyridines——a new class of multidrug resistance (MDR) modulators［J］.Bioorg Med Chem,2014,22(21):5860-5870.
[10]	Dostal V,Libusova L.Microtubule drugs: action, selectivity, and resistance across the kingdoms of life［J］.Protoplasma,2014,251(5):991-1005.
[11]	Hu T,Li Z,Gao CY,et al.Mechanisms of drug resistance in colon cancer and its therapeutic strategies［J］.World J Gastroenterol,2016,22(30):6876-6889.
[12]	Kavallaris M.Microtubules and resistance to tubulin-binding agents［J］.Nat Rev Cancer,2010,10(3):194-204.
[13]	Kavallaris M,Annereau JP,Barret JM.Potential mechanisms of resistance to microtubule inhibitors［J］.Semin Oncol,2008,35(3 Suppl 3):S22-S27.
[14]	Gan PP,Pasquier E,Kavallaris M.Class Ⅲ beta-tubulin mediates sensitivity to chemotherapeutic drugs in non small cell lung cancer［J］.Cancer Res,2007,67(19):9356-9363.
[15]	Amos LA.What tubulin drugs tell us about microtubule structure and dynamics［J］.Semin Cell Dev Biol,2011,22(9):916-926.
[16]	Löwe J,Li H,Downing KH,et al.Refined structure of αβ-tubulin at 3.5 Å resolution［J］.J Mol Biol,2001,313(5):1045-1057.
[17]	Devambatla RK,Namjoshi OA,Choudhary S,et al.Design, synthesis, and preclinical evaluation of 4-substituted-5-methyl-furo[2,3-d]pyrimidines as microtubule targeting agents that are effective against multidrug resistant cancer cells［J］.J Med Chem,2016,59(12):5752-5765.
[18]	Philchenkov AA,Zavelevich MP,Tryndyak VP,et al.Antiproliferative and proapoptotic effects of a pyrrole containing arylthioindole in human Jurkat leukemia cell line and multidrug-resistant Jurkat/A4 cells［J］.Cancer Biol Ther,2015,16(12):1820-1829.
[19]	Gan PP,McCarroll JA,Po'uha ST,et al.Microtubule dynamics, mitotic arrest, and apoptosis: drug-induced differential effects of betaⅢ-tubulin［J］.Mol Cancer Ther,2010,9(5):1339-1348.
[20]	Lu Y,Chen J,Xiao M,et al.An overview of tubulin inhibitors that interact with the colchicine binding site［J］.Pharm Res,2012,29(11):2943-2971.
[21]	Chamberlain MC,Grimm S,Phuphanich S,et al.A phase 2 trial of verubulin for recurrent glioblastoma: a prospective study by the Brain Tumor Investigational Consortium (BTIC)［J］.J Neurooncol,2014,118(2):335-343.
[22]	Kasibhatla S,Baichwal V,Cai SX,et al.MPC-6827: a small-molecule inhibitor of microtubule formation that is not a substrate for multidrug resistance pumps［J］.Cancer Res,2007,67(12):5865-5871.
[23]	Subbiah IM,Lenihan DJ,Tsimberidou AM.Cardiovascular toxicity profiles of vascular-disrupting agents［J］.Oncologist,2011,16(8):1120-1130.
[24]	Mahal K,Resch M,Ficner R,et al.Effects of the tumor-vasculature-disrupting agent verubulin and two heteroaryl analogues on cancer cells, endothelial cells, and blood vessels［J］.ChemMedChem,2014,9(4):847-854.
[25]	Wang XF,Guan F,Ohkoshi E,et al.Optimization of 4-(N-cycloamino)phenylquinazolines as a novel class of tubulin-polymerization inhibitors targeting the colchicine site［J］.J Med Chem,2014,57(4):1390-1402.
[26]	Gangjee A,Zhao Y,Raghavan S,et al.Structure-activity relationship and in vitro and in vivo evaluation of the potent cytotoxic anti-microtubule agent N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride and its analogues as antitumor agents［J］.J Med Chem,2013,56(17):6829-6844.
[27]	Cao D,Liu Y,Yan W,et al.Design, synthesis, and evaluation of in vitro and in vivo anticancer activity of 4-substituted coumarins: A novel class of potent tubulin polymerization inhibitors［J］.J Med Chem,2016,59(12):5721-5739.
[28]	Zhou B,Xing C.Diverse molecular targets for chalcones with varied bioactivities［J］.Med Chem (Los Angeles),2015,5(8):388-404.
[29]	Gwaltney SL,Imade HM,Barr KJ,et al.Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents［J］.Bioorg Med Chem Lett,2001,11(7):871-874.
[30]	Romagnoli R,Baraldi PG,Brancale A,et al.Convergent synthesis and biological evaluation of 2-amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents［J］.J Med Chem,2011,54(14):5144-5153.
[31]	Schobert R,Biersack B,Dietrich A,et al.4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and -N-methylimidazoles that are cytotoxic against combretastatin: A resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model［J］.J Med Chem,2010,53(18):6595-6602.
[32]	Nathwani SM,Hughes L,Greene LM,et al.Novel cis-restricted beta-lactam combretastatin A-4 analogues display anti-vascular and anti-metastatic properties in vitro［J］.Oncol Rep,2013,29(2):585-594.
[33]	Cai D,Qiu Z,Yao W,et al.YSL-12,a novel microtubule-destabilizing agent, exerts potent anti-tumor activity against colon cancer in vitro and in vivo［J］.Cancer Chemother Pharmacol,2016,77(6):1217-1229.
[34]	Mahal K,Biersack B,Schruefer S,et al.Combretastatin A-4 derived 5-(1-methyl-4-phenyl-imidazol-5-yl)indoles with superior cytotoxic and anti-vascular effects on chemoresistant cancer cells and tumors［J］.Eur J Med Chem,2016,118:9-20.
[35]	La Regina G,Bai R,Rensen W,et al.Design and synthesis of 2-heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability［J］.J Med Chem,2011,54(24):8394-8406.
[36]	An B,Zhang S,Yan J,et al.Synthesis, in vitro and in vivo evaluation of new hybrids of millepachine and phenstatin as potent tubulin polymerization inhibitors［J］.Org Biomol Chem,2017,15(4):852-862.
[37]	Romagnoli R,Baraldi PG,Salvador MK,et al.Discovery and optimization of a series of 2-aryl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazoles as novel anticancer agents［J］.J Med Chem,2012,55(11):5433-5445.
[38]	Hwang DJ,Wang J,Li W,et al.Structural optimization of indole derivatives acting at colchicine binding site as potential anticancer agents［J］.ACS Med Chem Lett,2015,6(9):993-997.
[39]	Romagnoli R,Baraldi PG,Salvador MK,et al.Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b]thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents［J］.J Med Chem,2013,56(6):2606-2618.
[40]	Wang X,Wu E,Wu J,et al.An antimitotic and antivascular agent BPR0L075 overcomes multidrug resistance and induces mitotic catastrophe in paclitaxel-resistant ovarian cancer cells［J］.PLoS ONE,2013,8(6):e65686.
[41]	Romagnoli R,Baraldi PG,Salvador MK,et al.Synthesis, antimitotic and antivascular activity of 1-(3',4',5'-trimethoxybenzoyl)-3-arylamino-5-amino-1,2,4-triazoles［J］.J Med Chem,2014,57(15):6795-6808.
[42]	Zhou B,Yu X,Zhuang C,et al.Unambiguous identification of beta-tubulin as the direct cellular target responsible for the cytotoxicity of chalcone by photoaffinity labeling［J］.Chem Med Chem,2016,11(13):1436-1445.
[43]	Yang Z,Wu W,Wang J,et al.Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors［J］.J Med Chem,2014,57(19):7977-7989.
[44]	Wang G,Li C,He L,et al.Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents［J］.Bioorg Med Chem,2014,22(7):2060-2079.
[45]	Zhu C,Zuo Y,Wang R,et al.Discovery of potent cytotoxic ortho-aryl chalcones as new scaffold targeting tubulin and mitosis with affinity-based fluorescence［J］.J Med Chem,2014,57(15):6364-6382.
[46]	Yan J,Chen J,Zhang S,et al.Synthesis, evaluation, and mechanism study of novel indole-chalcone derivatives exerting effective antitumor activity through microtubule destabilization in vitro and in vivo［J］.J Med Chem,2016,59(11):5264-5283.
[47]	Aoyama A,Katayama R,Oh-Hara T,et al.Tivantinib (ARQ 197) exhibits antitumor activity by directly interacting with tubulin and overcomes ABC transporter-mediated drug resistance［J］.Mol Cancer Ther,2014,13(12):2978-2990.
[48]	Eurtivong C,Semenov V,Semenova M,et al.3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells［J］.Bioorg Med Chem,2017,25(2):658-664.
[49]	Zheng YB,Gong JH,Liu XJ,et al.A Novel nitrobenzoate microtubule inhibitor that overcomes multidrug resistance exhibits antitumor activity［J］.Sci Rep,2016,6:31472.
[50]	Nakagawa-Goto K,Oda A,Hamel E,et al.Development of a novel class of tubulin inhibitor from desmosdumotin B with a hydroxylated bicyclic B-ring［J］.J Med Chem,2015,58(5):2378-2389.
[51]	Lee WH,Liu HE,Chang JY,et al.MPT0B169, a new tubulin inhibitor, inhibits cell growth and induces G2/M arrest in nonresistant and paclitaxel-resistant cancer cells［J］.Pharmacology,2013,92(1-2):90-98.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers

1. Department of Medicinal Chemistry, School of Pharmacy, Nanjing Medical University, Nanjing 211166, China

2. Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2017-05-03

Rev Recd Date: 2017-06-19

Key words:

Abstract: In 2015, more than 8 million people died from various kinds of cancers all over the world. Although traditional chemotherapeutic drugs are widely used in clinic, more than 50% of cancers are significantly resistant to traditional chemotherapeutic drugs. Tubulin targeting agents have been confirmed to be effective anti-cancer drugs in clinic. However, some anti-microtubule agents developed resistance after long-term use, such as paclitaxel and vinblastine. In recent years, it is reported that tubulin modulators targeting on the colchicine-binding site are extremely effective against multi-drug resistant cancer cells. In this article, different anti-microtubule agents targeting multi-drug resistant cancers are reviewed.

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Reference (51)

[1]	Parker AL,Kavallaris M,McCarroll JA.Microtubules and their role in cellular stress in cancer［J］.Front Oncol,2014,4:153.
[2]	Prosser SL,Pelletier L.Mitotic spindle assembly in animal cells: a fine balancing act［J］.Nat Rev Mol Cell Biol,2017,18(3):187-201.
[3]	Jordan MA,Wilson L.Microtubules as a target for anticancer drugs［J］.Nat Rev Cancer,2004,4(4):253-265.
[4]	Li W,Zhang H,Assaraf YG,et al.Overcoming ABC transporter-mediated multidrug resistance: Molecular mechanisms and novel therapeutic drug strategies［J］.Drug Resist Updat,2016,27:14-29.
[5]	Krishna R,Mayer LD.Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs［J］.Eur J Pharm Sci,2000,11(4):265-283.
[6]	Hao XY,Widersten M,Ridderstrom M,et al.Co-variation of glutathione transferase expression and cytostatic drug resistance in HeLa cells: establishment of class Mu glutathione transferase M3-3 as the dominating isoenzyme［J］.Biochem J,1994,297 (Pt 1):59-67.
[7]	Ogiso Y,Tomida A,Tsuruo T.Nuclear localization of proteasomes participates in stress-inducible resistance of solid tumor cells to topoisomerase Ⅱ-directed drugs［J］.Cancer Res,2002,62(17):5008-5012.
[8]	Fernald K,Kurokawa M.Evading apoptosis in cancer［J］.Trends Cell Biol,2013,23(12):620-633.
[9]	Krauze A,Grinberga S,Krasnova L,et al.Thieno[2,3-b]pyridines——a new class of multidrug resistance (MDR) modulators［J］.Bioorg Med Chem,2014,22(21):5860-5870.
[10]	Dostal V,Libusova L.Microtubule drugs: action, selectivity, and resistance across the kingdoms of life［J］.Protoplasma,2014,251(5):991-1005.
[11]	Hu T,Li Z,Gao CY,et al.Mechanisms of drug resistance in colon cancer and its therapeutic strategies［J］.World J Gastroenterol,2016,22(30):6876-6889.
[12]	Kavallaris M.Microtubules and resistance to tubulin-binding agents［J］.Nat Rev Cancer,2010,10(3):194-204.
[13]	Kavallaris M,Annereau JP,Barret JM.Potential mechanisms of resistance to microtubule inhibitors［J］.Semin Oncol,2008,35(3 Suppl 3):S22-S27.
[14]	Gan PP,Pasquier E,Kavallaris M.Class Ⅲ beta-tubulin mediates sensitivity to chemotherapeutic drugs in non small cell lung cancer［J］.Cancer Res,2007,67(19):9356-9363.
[15]	Amos LA.What tubulin drugs tell us about microtubule structure and dynamics［J］.Semin Cell Dev Biol,2011,22(9):916-926.
[16]	Löwe J,Li H,Downing KH,et al.Refined structure of αβ-tubulin at 3.5 Å resolution［J］.J Mol Biol,2001,313(5):1045-1057.
[17]	Devambatla RK,Namjoshi OA,Choudhary S,et al.Design, synthesis, and preclinical evaluation of 4-substituted-5-methyl-furo[2,3-d]pyrimidines as microtubule targeting agents that are effective against multidrug resistant cancer cells［J］.J Med Chem,2016,59(12):5752-5765.
[18]	Philchenkov AA,Zavelevich MP,Tryndyak VP,et al.Antiproliferative and proapoptotic effects of a pyrrole containing arylthioindole in human Jurkat leukemia cell line and multidrug-resistant Jurkat/A4 cells［J］.Cancer Biol Ther,2015,16(12):1820-1829.
[19]	Gan PP,McCarroll JA,Po'uha ST,et al.Microtubule dynamics, mitotic arrest, and apoptosis: drug-induced differential effects of betaⅢ-tubulin［J］.Mol Cancer Ther,2010,9(5):1339-1348.
[20]	Lu Y,Chen J,Xiao M,et al.An overview of tubulin inhibitors that interact with the colchicine binding site［J］.Pharm Res,2012,29(11):2943-2971.
[21]	Chamberlain MC,Grimm S,Phuphanich S,et al.A phase 2 trial of verubulin for recurrent glioblastoma: a prospective study by the Brain Tumor Investigational Consortium (BTIC)［J］.J Neurooncol,2014,118(2):335-343.
[22]	Kasibhatla S,Baichwal V,Cai SX,et al.MPC-6827: a small-molecule inhibitor of microtubule formation that is not a substrate for multidrug resistance pumps［J］.Cancer Res,2007,67(12):5865-5871.
[23]	Subbiah IM,Lenihan DJ,Tsimberidou AM.Cardiovascular toxicity profiles of vascular-disrupting agents［J］.Oncologist,2011,16(8):1120-1130.
[24]	Mahal K,Resch M,Ficner R,et al.Effects of the tumor-vasculature-disrupting agent verubulin and two heteroaryl analogues on cancer cells, endothelial cells, and blood vessels［J］.ChemMedChem,2014,9(4):847-854.
[25]	Wang XF,Guan F,Ohkoshi E,et al.Optimization of 4-(N-cycloamino)phenylquinazolines as a novel class of tubulin-polymerization inhibitors targeting the colchicine site［J］.J Med Chem,2014,57(4):1390-1402.
[26]	Gangjee A,Zhao Y,Raghavan S,et al.Structure-activity relationship and in vitro and in vivo evaluation of the potent cytotoxic anti-microtubule agent N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride and its analogues as antitumor agents［J］.J Med Chem,2013,56(17):6829-6844.
[27]	Cao D,Liu Y,Yan W,et al.Design, synthesis, and evaluation of in vitro and in vivo anticancer activity of 4-substituted coumarins: A novel class of potent tubulin polymerization inhibitors［J］.J Med Chem,2016,59(12):5721-5739.
[28]	Zhou B,Xing C.Diverse molecular targets for chalcones with varied bioactivities［J］.Med Chem (Los Angeles),2015,5(8):388-404.
[29]	Gwaltney SL,Imade HM,Barr KJ,et al.Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents［J］.Bioorg Med Chem Lett,2001,11(7):871-874.
[30]	Romagnoli R,Baraldi PG,Brancale A,et al.Convergent synthesis and biological evaluation of 2-amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents［J］.J Med Chem,2011,54(14):5144-5153.
[31]	Schobert R,Biersack B,Dietrich A,et al.4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and -N-methylimidazoles that are cytotoxic against combretastatin: A resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model［J］.J Med Chem,2010,53(18):6595-6602.
[32]	Nathwani SM,Hughes L,Greene LM,et al.Novel cis-restricted beta-lactam combretastatin A-4 analogues display anti-vascular and anti-metastatic properties in vitro［J］.Oncol Rep,2013,29(2):585-594.
[33]	Cai D,Qiu Z,Yao W,et al.YSL-12,a novel microtubule-destabilizing agent, exerts potent anti-tumor activity against colon cancer in vitro and in vivo［J］.Cancer Chemother Pharmacol,2016,77(6):1217-1229.
[34]	Mahal K,Biersack B,Schruefer S,et al.Combretastatin A-4 derived 5-(1-methyl-4-phenyl-imidazol-5-yl)indoles with superior cytotoxic and anti-vascular effects on chemoresistant cancer cells and tumors［J］.Eur J Med Chem,2016,118:9-20.
[35]	La Regina G,Bai R,Rensen W,et al.Design and synthesis of 2-heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability［J］.J Med Chem,2011,54(24):8394-8406.
[36]	An B,Zhang S,Yan J,et al.Synthesis, in vitro and in vivo evaluation of new hybrids of millepachine and phenstatin as potent tubulin polymerization inhibitors［J］.Org Biomol Chem,2017,15(4):852-862.
[37]	Romagnoli R,Baraldi PG,Salvador MK,et al.Discovery and optimization of a series of 2-aryl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazoles as novel anticancer agents［J］.J Med Chem,2012,55(11):5433-5445.
[38]	Hwang DJ,Wang J,Li W,et al.Structural optimization of indole derivatives acting at colchicine binding site as potential anticancer agents［J］.ACS Med Chem Lett,2015,6(9):993-997.
[39]	Romagnoli R,Baraldi PG,Salvador MK,et al.Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b]thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents［J］.J Med Chem,2013,56(6):2606-2618.
[40]	Wang X,Wu E,Wu J,et al.An antimitotic and antivascular agent BPR0L075 overcomes multidrug resistance and induces mitotic catastrophe in paclitaxel-resistant ovarian cancer cells［J］.PLoS ONE,2013,8(6):e65686.
[41]	Romagnoli R,Baraldi PG,Salvador MK,et al.Synthesis, antimitotic and antivascular activity of 1-(3',4',5'-trimethoxybenzoyl)-3-arylamino-5-amino-1,2,4-triazoles［J］.J Med Chem,2014,57(15):6795-6808.
[42]	Zhou B,Yu X,Zhuang C,et al.Unambiguous identification of beta-tubulin as the direct cellular target responsible for the cytotoxicity of chalcone by photoaffinity labeling［J］.Chem Med Chem,2016,11(13):1436-1445.
[43]	Yang Z,Wu W,Wang J,et al.Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors［J］.J Med Chem,2014,57(19):7977-7989.
[44]	Wang G,Li C,He L,et al.Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents［J］.Bioorg Med Chem,2014,22(7):2060-2079.
[45]	Zhu C,Zuo Y,Wang R,et al.Discovery of potent cytotoxic ortho-aryl chalcones as new scaffold targeting tubulin and mitosis with affinity-based fluorescence［J］.J Med Chem,2014,57(15):6364-6382.
[46]	Yan J,Chen J,Zhang S,et al.Synthesis, evaluation, and mechanism study of novel indole-chalcone derivatives exerting effective antitumor activity through microtubule destabilization in vitro and in vivo［J］.J Med Chem,2016,59(11):5264-5283.
[47]	Aoyama A,Katayama R,Oh-Hara T,et al.Tivantinib (ARQ 197) exhibits antitumor activity by directly interacting with tubulin and overcomes ABC transporter-mediated drug resistance［J］.Mol Cancer Ther,2014,13(12):2978-2990.
[48]	Eurtivong C,Semenov V,Semenova M,et al.3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells［J］.Bioorg Med Chem,2017,25(2):658-664.
[49]	Zheng YB,Gong JH,Liu XJ,et al.A Novel nitrobenzoate microtubule inhibitor that overcomes multidrug resistance exhibits antitumor activity［J］.Sci Rep,2016,6:31472.
[50]	Nakagawa-Goto K,Oda A,Hamel E,et al.Development of a novel class of tubulin inhibitor from desmosdumotin B with a hydroxylated bicyclic B-ring［J］.J Med Chem,2015,58(5):2378-2389.
[51]	Lee WH,Liu HE,Chang JY,et al.MPT0B169, a new tubulin inhibitor, inhibits cell growth and induces G2/M arrest in nonresistant and paclitaxel-resistant cancer cells［J］.Pharmacology,2013,92(1-2):90-98.

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Recent research progress on anti-microtubule agents targeting multi-drug resistant cancers

doi: 10.3969/j.issn.1006-0111.2017.05.001

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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