Indole molecules as inhibitors of tubulin polymerization: Potential new anticancer agents

Future Medicinal Chemistry

Volumn 4, Issue 16, 2012, Pages 2085-2115

  Patil, Shivaputra A ^a   Patil, Renukadevi ^a   Miller, Duane D ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AROYLINDOLE DERIVATIVE; 3 AROYLINDOLE DERIVATIVE; 3 FORMYL 2 PHENYLINDOLE DERIVATIVE; ALPHA TUBULIN; ANTINEOPLASTIC AGENT; ARYLTHIOINDOLE DERIVATIVE; BETA TUBULIN; COLCHICINE; COMBRETASTATIN A4; CROLIBULIN; D 64131; DENIBULIN; DIARYLINDOLE DERIVATIVE; GAMMA TUBULIN; INDIBULIN; INDOLE DERIVATIVE; INDOLYLGLYOXYAMIDE DERIVATIVE; MICROTUBULE ASSOCIATED PROTEIN; MULTIDRUG RESISTANCE PROTEIN 1; N [2 [(4 HYDROXYPHENYL)AMINO] 3 PYRIDINYL] 4 METHOXYBENZENESULFONAMIDE; PLINABULIN; UNCLASSIFIED DRUG; VERUBULIN;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CELL CYCLE ARREST; DRUG BINDING SITE; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; DRUG TARGETING; FRIEDEL CRAFTS REACTION; HUMAN; LEUKEMIA CELL LINE; MELANOMA; MICHAEL ADDITION; MICROTUBULE ASSEMBLY; MITOSIS; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; HUMANS; INDOLES; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 84869460356     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.12.141     Document Type: Review

References (118)

1. Lalit K, Shashi B, Kamal J. The diverse pharmacological importance of indole derivatives: a review. Intl J. Res. Pharm. Sci. 2, 23-33 (2012).
2. Wang G, Geng L. Statistical and generalized two-dimensional correlation spectroscopy of multiple ionization states, fuorescence of neurotransmitter serotonin. Anal. Chem. 77, 20-29 (2005).
3. 1H and molecular modeling study on the inclusion complex beta-cyclodextrin-indomethacin. J. Org. Chem. 61, 909-914 (1996).
4. Isaac MT. Review: combining pindolol with an SSRI improves early outcomes in people with depression. Evid. Based Ment. Health 7, 107 (2004).
5. Hurdle JG, O'Neill AJ, Chopra I. Anti-staphylococcal activity of indo lmycin, a potential topical agent for control of staphylococcal infections. J. Antimicrob. Chemother. 54, 549-552 (2004).
6. Sheftel FD, Bigal ME, Tepper SJ, Rapaport AM. Sumatriptan: a decade of use and experience in the treatment of migraine. Expert Rev. Neurother. 4, 199-209 (2004).
7. Kronig B, Pittrow DB, Kirch W, Welzel D, Weidinger G. Different concepts in frst-line treatment of essential hypertension. Comparison of a low-dose reserpine-thiazide combination with nitrendipine monotherapy. German Reserpine in Hypertension Study Group. Hypertension 29, 651-658 (1997).
8. de Sá Alves FR, Barreiro EJ, Fraga CA. From nature to drug discovery: the indole scaffold as a 'privileged structure'. Mini Rev. Med. Chem. 9, 782-793 (2009).
9. Horton DA, Bourne GT, Smythe ML. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev. 103, 893-930 (2003).
10. Patil SA, Patil R, Miller DD. Microwave-assisted synthesis of medicinally relevant indoles. Curr. Med. Chem. 18, 615-637 (2011).
11. Patil SA, Patil R, Miller DD. Solid phase synthesis of biologically important indoles. Curr. Med. Chem. 16, 2531-2565 (2009).
12. Patil SA, Patil R, Miller DD. Synthetic applications of the Nenitzescu reaction to biologically active 5-hydroxyindoles. Curr. Org. Chem. 12, 691-717 (2008).
13. Patil SA, Patil R. Synthesis and functionalization of Indoles through Rhodium-catalyzed reactions. Curr. Org. Synt. 4, 201-222 (2007).
14. Patil S, Buolamwini JK. Recent uses of palladium chemistry in indole synthesis. Curr. Org. Synt. 3, 477-498 (2006).
15. Weng J-R, Tsai C-H, Kulp SK, Chen C-S. Indole-3-carbinol as a chemopreventive and anti-cancer agent. Cancer Lett. 262, 153-163 (2008).
16. Rieck GC, Fiander AN. Human papillomavirus, cervical carcinogenesisand chemoprevention with indole derivates-a review of pathomechanisms. Mol. Nutr. Food Res. 52, 105-113 (2008).
17. Humphrey GR, Kuethe JT. Practical methodologies for the synthesis of indoles. Chem. Rev. 106, 2875-2911 (2006).
18. Cacchi S, Fabrizi G. Synthesis and functionalization of indoles through palladium-catalyzed reactions. Chem. Rev. 105, 2873-2920 (2005).
19. Li JJ, Gribble GW. Palladium in Heterocyclic Chemistry. Pergamon, Oxford, UK, 73 (2000).
20. Gribble GW. Recent developments in indole ring synthesismethodology and applications. J. Chem. Soc. Perkin Trans. 1, 1045-1047 (2000).
21. KetchaDM, Wilson LJ, Portlock DE. The solid-phase Nenitzescu indole synthesis. Te t. Lett. 41, 6253-6257 (2000).
22. Tois J, Franzen R, Koskinen A. Synthetic approaches towards indoles on solid phase recent advances and future directions. Tetrahedron 59, 5395-5405 (2003).
23. Dalpozzo R, Bartoli G. Bartoli indole synthesis. Curr. Org. Chem. 9, 163-178 (2005).
24. Biswal S, Sahoo U, Sethy S, Kumar HKS, Banerjee M. Indole: the molecule of diverse biological activities. Asian J. Pharm. Clin. Res. 5(1), 1-6 (2012).
25. Brase S, Gil C, Knepper K. The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles. Bioorg. Med. Chem. 10, 2415-2437 (2002).
26. Gil C, Brase S. Solid-phase synthesis of biologically active benzoannelated nitrogen heterocycles: an update. J. Comb. Chem. 11, 175-197 (2009).
27. Jordan MA, Wilson L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 4, 253-265 (2004).
28. Dumontet C, Jordan MA. Microtubule-binding agents: a dynamic feld of cancer therapeutics. Nat. Rev. Drug Discov. 9, 790-803 (2010).
29. Downing KH, Nogales E. Tubulin and microtubule structure. Curr. Opin. Cell Biol. 10, 16-22 (1998).
30. Jordan MA. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr. Med. Chem. Anticancer Agents 1, 1-17 (2002).
31. Dumontet C, Sikic BI. Mechanisms of action of and resistance to antitubulin agents: microtubule dynamics, drug transport, and cell death. J. Clin. Oncol. 17, 1061-1070 (1999).
32. Holland JF, Scharlau C, Gailani S et al. Vincristine treatment of advanced cancer: a cooperative study of 392 cases. Cancer Res. 33, 1258-1264 (1973).
33. ®). Semin. Oncol. Nurs. 9, 2-5 (1993).
34. Hussain M, Wozniak AJ, Edelstein MB. Neurotoxicity of antineoplastic agents. Crit. Rev. Oncol. Hematol. 14, 61-75 (1993).
35. Cavaletti G, Cavalletti E, Montaguti P, Oggioni N, De-Negri O, Tredici G. Effect on the peripheral nervous system of the short-term intravenous administration of paclitaxel in the rat. Neurotoxicology 18, 137-145 (1997).
36. Gwaltney SL, Imade HM, Barr KJ et al. Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents. Bioorg. Med. Chem. Lett. 11, 871-874 (2001).
37. Pettit GR, Singh SB, Boyd MR et al. Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6(1a). J. Med. Chem. 38, 1666-1672 (1995).
38. Lee RM, Gewirtz DA. Colchicine site inhibitors of microtubule integrity as vascular disrupting agents. Drug Dev. Res. 69, 352-358 (2008).
39. Lippert JW. Vascular disrupting agents. Bioorg. Med. Chem. 15, 605-615 (2007).
40. Kasibhatla S, Gourdeau H, Meerovitch K et al. Discovery and mechanism of action of a novel series of apoptosis inducers with potential vascular targeting activity. Mol. Cancer Ther. 3, 1365-1374 (2004).
41. Tron GC, Pirali T, Sorba G, Pagliai F, Busacca S, Genazzani AA. Medicinal chemistry of combretastatin A4: present and future directions. J. Med. Chem. 49, 3033-3044 (2006).
42. Singh R, Kaur H. Advances in synthetic approaches for the preparation of combretastatin-based anti-cancer agents. Synthesis 15, 2471-2491 (2009).
43. Grosios K, Holwell SE, McGown AT, Pettit GR, Bibby MC. In vivo and in vitro evaluation of combretastatin A-4 and its sodium phosphate prodrug. Br. J. Cancer 81, 1318-1327 (1999).
44. Patterson DM, Rustin GJS. combretastatin A4 phosphate. Drugs Future 32, 1025-1032 (2007).
45. Rudin CM, Mauer A, Smakal M et al. Phase I/II study of pemetrexed with or without ABT-751 in advanced or metastatic non-small-cell lung cancer. J. Clin. Oncol. 29(8), 1075-1082 (2011).
46. Fox E, Maris JM, Cohn SL et al. Pharmacokinetics of orally administered ABT-751 in children with neuroblastoma and other solid tumors. Cancer Chemother. Pharmacol. 66(4), 737-743 (2010).
47. Meany HJ, Sackett DL, Maris JM et al. Clinical outcome in children with recurrent neuroblastoma treated with ABT-751and effect of ABT-751 on proliferation of neuroblastoma cell lines and on tubulin polymerization in vitro. Pediatr. Blood Cancer 54(1), 47-54 (2010).
48. Michels J, Ellard SL, Le L et al. A Phase IB study of ABT-751 in combination with docetaxel in patients with advanced castration-resistant prostate cancer. Ann. Oncol. 21(2), 305-311 (2010).
49. 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. Clin. Cancer Res. 14(4), 1111-1115 (2008).
50. Nicholson B, Lloyd GK, Miller BR et al. NPI-2358 is a tubulindepolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anticancer Drugs 17, 25-31 (2006).
51. Millward M, Mainwaring P, Mita A et al. Phase 1 study of the novel vascular disrupting agent plinabulin (NPI-2358) and docetaxel. Invest. New Drug. 30(3), 1065-1073 (2012).
52. Mita MM, Spear MA, Yee LK et al. Phase 1 frst-in-human trial of the vascular disrupting agent plinabulin (NPI-2358) in patients with solid tumors or lymphomas. Clin. Cancer Res. 16(23), 5892-5899 (2010).
53. Kim LJ, Chamberlain MC, Zhu J et al. Phase 2 study of verubulin (MPC-6827) for the treatment of subjects with recurrent glioblastoma naïve to treatment with bevacizumab. Presented at: Annual Meeting of ASCO. June 3-7, Chicago, IL, USA (2011) (Abstract 2088).
54. 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. Mol. Cancer Ther. 9(12), 3410-3419 (2010).
55. Thomas P, Recht L. Verubulin hydrochloride. Drugs Fut. 35(12), 993 (2010).
56. Sirisoma N, Pervin A, Zhang H et al. Discovery of N-methyl-4-(4- methoxyanilino) quinazolines as potent apoptosis inducers. Structure-activity relationship of the quinazoline ring. Bioorg. Med. Chem. Lett. 20(7), 2330-2334 (2010).
57. Sirisoma N, Pervin A, Zhang H et al. Discovery of N-(4-methoxyphenyl)-N, 2-dimethylquinazolin-4-amine, a potent apoptosis inducer and effcacious anticancer agent with high blood brain barrier penetration. J. Med. Chem. 52, 2341-2351 (2009).
58. Cai SX, Drewe J, Kemnitzer W. Discovery of 4-aryl-4H-chromenes as potent apoptosis inducers using a cell-and caspase-based Anti-cancer Screening Apoptosis Program (ASAP): SAR studies and the identifcation of novel vascular disrupting agents. Anticancer Agents Med. Chem. 9(4), 437-456 (2009).
59. Cai SX. Small molecule vascular disrupting agents: potential new drugs for cancer treatment. Recent Pat. Anticancer Drug Discov. 2(1), 79-101 (2007).
60. ®), a novel vascular-disrupting agent, in patients with advanced solid tumors. Cancer Chemother. Pharmacol. 68(4), 959-970 (2011).
61. Traynor AM, Gordon MS, Alberti D et al. A dose escalation, safety, and tolerability study of MN-029 in patients with advanced solid tumors. Invest. New Drugs. 28(4), 509-515 (2010).
62. Shi W, Siemann DW. Preclinical studies of the novel vascular disrupting agent MN-029. Anticancer Res. 25(6B), 3899-3904 (2005).
63. Brancale A, Silvestri R. Indole, a core nucleus for potent inhibitors of tubulin polymerization. Med. Res. Rev. 27(2), 209-238 (2007).
64. Liou JP, Chang YL, Kuo FM et al. Concise synthesis and structure-activity relationships of combretastatin A-4 analogues, 1-aroylindoles and 3-aroylindoles, as novel classes of potent antitubulin agents. J. Med. Chem. 47(17), 4247-4257 (2004).
65. Alvarez R, Alvarez C, Mollinedo F, Sierra BG, Medarde M, Peláez R. Isocombretastatins A:1, 1-diarylethenes as potent inhibitors of tubulin polymerization and cytotoxic compounds. Bioorg. Med. Chem. 17(17), 6422-6431 (2009).
66. Kuo CC, Hsieh HP, Pan WY et al. BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 64(13), 4621-4628 (2004).
67. Liou JP, Wu ZY, Kuo CC et al. Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors. J. Med. Chem. 51(14), 4351-4355 (2008).
68. Liou JP, Wu CY, Hsieh HP et al. 4-and 5-aroylindoles as novel classes of potent antitubulin agents. J. Med. Chem. 50(18), 4548-4552 (2007).
69. Mahboobi S, Pongratz H, Hufsky H et al. Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents. J. Med. Chem. 44(26), 4535-4553 (2001).
70. Beckers T, Reissmann T, Schmidt M et al. 2-aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors. Cancer Res. 62(11), 3113-3119 (2002).
71. Ty N, Dupeyre G, Chabot GG et al. Synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(3́, 4́, 5́-trimethoxybenzoyl)-1H-indole (BPR0L075), as potential antivascular agents. Bioorg. Med. Chem. 16(15), 7494-7503 (2008).
72. Arthuis M, Pontikis R, Chabot GG, Quentin L, Scherman D, Florent JC. Domino approach to 2-aroyltrimethoxyindoles as novel heterocyclic combretastatin A4 analogues. Eur. J. Med. Chem. 46(1), 95-100 (2011).
73. Romagnoli R, Baraldi PG, Sarkar T et al. Synthesis and biological evaluation of 1-met hy l-2-(3́, 4́, 5́-t r i m et hox y ben z oyl)-3-amino indoles as a new class of antimitotic agents and tubulin inhibitors. J. Med. Chem. 51, 1464-1468 (2008).
74. Dupeyre G, Chabot GG, Thoret S et al. Synthesis and biological evaluation of (3, 4, 5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents. Bioorg. Med. Chem. 14(13), 4410-4426 (2006).
75. Flynn BL, Hamel E, Jung MK. One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization. J. Med. Chem. 45, 2670-2673 (2002).
76. Alvarez C, Alvarez R, Corchete P et al. Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization. Bioorg. Med. Chem. 16, 5952-5961 (2008).
77. Alvarez C, Alvarez R, Corchete P, Pérez-Melero C, Peláez R, Medarde M. Exploring the effect of 2, 3, 4-trimethoxy-phenyl moiety as a component of indolephenstatins. Eur. J. Med. Chem. 45, 588-597 (2010).
78. De Martino G, La Regina G, Coluccia A et al. Arylthioindoles, potent inhibitors of tubulin polymerization. J. Med. Chem. 47, 6120-6123 (2004).
79. De Martino G, Edler MC, La Regina G et al. New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies. J. Med. Chem. 49, 947-954 (2006).
80. La Regina G, Edler MC, Brancale A et al. Arylthioindole inhibitors of tubulin polymerization. 3. Biological evaluation, structure-activity relationships and molecular modeling studies. J. Med. Chem. 50, 2865-2874 (2007).
81. La Regina G, Sarkar T, Bai R et al. New arylthioindoles and related bioisosteres at the sulfur bridging group. 4. Synthesis, tubulin polymerization, cell growth inhibition, and molecular modeling studies. J. Med. Chem. 52, 7512-7527 (2009).
82. 1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability. J. Med. Chem. 54, 8394-8406 (2011).
83. Liou J-P, Chang C-W, Song J-S et al. Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents. J. Med. Chem. 45, 2556-2562 (2002).
84. Chang J-Y, Yang M-F, Chang C-Y, Chen C-M, Kuo C-C, Liou J-P. 2-amino and 2́-aminocombretastatin derivatives as potent antimitotic agents. J. Med. Chem. 49, 6412-6415 (2006).
85. Romagnoli R, Baraldi PG, Pavani MG et al. Synthesis and biological evaluation of 2-amino-3-(3́, 4́, 5́-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulin agents. J. Med. Chem. 49, 3906-3915 (2006).
86. Romagnoli R, Baraldi PG, Remusat V et al. Synthesis and biological evaluation of 2-(3́, 4́, 5́-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. J. Med. Chem. 49, 6425-6428 (2006).
87. Ravelli RBG, Gigant B, Curmi PA et al. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 428, 198-202 (2004).
88. Medarde M, Ramos AC, Caballero E et al. Synthesis and pharmacological activity of diarylindole derivatives. Cytotoxic agents based on combretastatins. Bioorg. Med. Chem. Lett. 9, 2303-2308 (1999).
89. Goldbrunner M, Loidl G, Polossek T, Mannschreck A, von Angerer E. Inhibition of tubulin polymerization by 5, 6-dihydroindolo[2, 1-a]isoquinoline derivatives. J. Med. Chem. 40, 3524-3533 (1997).
90. Gastpar R, Goldbrunner M, Marko D, von Angerer E. Methoxy-substituted 3-formyl-2-phenylindoles inhibit tubulin polymerization. J. Med. Chem. 41, 4965-4972 (1998).
91. Kaufmann D, Pojarová M, Vogel S et al. Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells. Bioorg. Med. Chem. 15, 5122-5136 (2007).
92. Pojarova M, Kaufmann D, Gastpar R et al. [(2-Phenylindol-3-yl)methylene] propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis. Bioorg. Med. Chem. 15, 7368-7379 (2007).
93. Vogel S, Kaufmann D, Pojarová M et al. Aroyl hydrazones of 2-phenylindole-3-carbaldehydes as novel antimitotic agents. Bioorg. Med. Chem. 16, 6436-6447 (2008).
94. Knaack M, Emig P, Bats JW, Kiesel M, Muller A, Gunther E. Synthesis and characterization of the biologically active 2-[1-(4-chlorobenzyl)-1H-indol-3-yl] -2-oxo-N-pyridin-4-yl acetamide. Eur. J. Org. Chem. 20, 3843-3847 (2001).
95. Li WT, Hwang DR, Chen CP et al. Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents. J. Med. Chem. 46(9), 1706-1715 (2003).
96. Marchand P, Antoine M, Le Baut G, Czech M, Baasner S, Günther E. Synthesis and structure-activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents. Bioorg. Med. Chem. 17(18), 6715-6727 (2009).
97. Semenova MN, Kiselyov AS, Titov IY et al. In vivo evaluation of indolyl glyoxamides in the phenotypic sea urchin embryo assay. Chem. Biol. Drug Des. 70(6), 485-490 (2007).
98. Bacher G, Beckers T, Emig P, Klenner T, Kutscher B, Nickel B. New small-molecule tubulin inhibitors. Pure Appl. Chem. 73, 1459-1464 (2001).
99. Bacher G, Nickel B, Emig P et al. D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows effcacy toward multidrug-resistant tumor cells, and lacks neurotoxicity. Cancer Res. 6, 392-399 (2001).
100. Ahn S, Hwang DJ, Barrett CM et al. A novel bis-indole destabilizes microtubules and displays potent in vitro and in vivo antitumor activity in prostate cancer. Cancer Chemother. Pharmacol. 67(2), 293-304 (2011).
101. Ahn S, Duke CB 3rd, Barrett CM et al. I-387, a novel antimitotic indole, displays a potent in vitro and in vivo antitumor activity with less neu rotoxicity. Mol. Cancer Ther. 9(11), 2859-2868 (2010).
102. Lee HY, Chang JY, Chang LY et al. Concise syntheses of N-aryl-5, 6, 7-trimethoxyindoles as antimitotic and vascular disrupting agents: application of the copper-mediated Ullmann-type arylation. Org. Biomol. Chem. 9, 3154-3157 (2011).
103. Lai MJ, Chang J Y, Lee HY et al. Synthesis and biological evaluation of 1-(4-indolyl and 6-quinolinyl) indoles as a new class of potent anticancer agents. Eur. J. Med. Chem. 46, 3623-3629 (2011).
104. Chang J Y, Lai MJ, Chang YT et al. Synthesis and biological evaluation of 7-arylindoline-1-benzenesulfonamides as a novel class of potent anticancer agents. Med. Chem. Commun. 1, 152-155 (2010).
105. Hu L, Li ZR, Wang YM, Wu Y, Jiang JD, Boykin DW. Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents. Bioorg. Med. Chem. Lett. 17, 1193-1196 (2007).
106. Hu L, Jiang JD, Qu J et al. Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure-activity relationships. Bioorg. Med. Chem. Lett. 1 7, 3613-3617 (2007).
107. Xie F, Zhao H, Li D et al. Synthesis and biological evaluation of 2, 4, 5-substituted pyrimidines as a new class of tubulin polymerization inhibitors. J. Med. Chem. 54, 3200-3205 (2011).
108. Ty N, Dupeyre G, Chabot GG et al. Structure-activity relationships of indole compounds derived from combretastatin A4: synthesis and biological screening of 5-phenylpyrrolo[3, 4-a]carbazole-1, 3-diones as potential antivascular agents. Eur. J. Med. Chem. 45(9), 3726-3739 (2010).
109. Putey A, Popowycz F, Do QT et al. Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: synthesis and structure-activity relationship studies. J. Med. Chem. 52(19), 5916-5925 (2009).
110. Keller L, Beaumont S, Liu JM et al. New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: cytotoxic and antitumor activities. J. Med. Chem. 51(12), 3414-3421 (2008).
111. Pons V, Beaumont S, Tran Huu Dau ME, Iorga B, Dodd RH. Rigid analogues of antimitotic indolobenzazepinones: new insights into tubulin binding via molecular modeling. ACS Med. Chem. Lett. 2(8), 565-570 (2011).
112. Gréen H, Rosenberg P, Söderkvist P, Horvath G, Peterson C. Beta-tubulin mutations in ovarian cancer using single strand conformation ana lysis-risk of false positive results from paraffn embedded tissues. Cancer Lett. 236(1), 148-154 (2006).
113. Cheung CH, Wu SY, Lee TR et al. Cancer cells acquire mitotic drug resistance properties through beta I-tubulin mutations and alterations in the expression of beta-tubulin isotypes. PLoS ONE 5(9), e12564 (2010).
114. Wang Y, Cabral F. Paclitaxel resistance in cells with reduced beta-tubulin. Biochim. Biophys. Acta 1744(2), 245-255 (2005).
115. Chen KG, Sikic BI. Molecular pathways: regulation and therapeutic implications of multidrug resistance. Clin. Cancer Res. 18(7), 1863-1869 (2012).
116. Sharom FJ. The P-glycoprotein multidrug transporter. Essays Biochem. 50(1), 161-178 (2011).
117. Leslie EM, Deeley RG, Cole SP. Multidrug resistance proteins: role of P-glycoprotein, MRP1, MRP2, and BCRP (ABCG2) in tissue defense. Toxicol. Appl. Pharmacol. 204(3), 216-237 (2005).
118. Smoter M, Bodnar L, Duchnowska R, Stec R, Grala B, Szczylik C. The role of Tau protein in resistance to paclitaxel. Cancer Chemother. Pharmacol. 68(3), 553-557 (2011).