CoChat
Sign Up
Cited by 709

The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.

An Overview of Tubulin Inhibitors That Interact with the Colchicine Binding Site

Lu, Yan, Chen, Jianjun, Xiao, Min, Li, Wei, Miller, Duane D.·2012·Pharmaceutical Research
DOI 10.1007/s11095-012-0828-zPMC PMC3667160
Open this paper in CoChat — free account

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1007/s11095-012-0828-z

Cites

1 of 1 references verified0 citation errors · 0 not checkable

Statistics

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

Flagged first, then by citations

Show all 1 references

Research works printed but not linked: 158

  1. Pryor DE, O'Brate A, Bilcer G, Diaz JF, Wang Y, Kabaki M, et al. The microtubule stabilizing agent laulimalide does not bind in the taxoid site, kills cells resistant to paclitaxel and epothilones, and may not require its epoxide moiety for activity. Biochemistry. 2002;41:9109–15. · DOI
  2. Gigant B, Wang C, Ravelli RB, Roussi F, Steinmetz MO, Curmi PA, et al. Structural basis for the regulation of tubulin by vinblastine. Nature. 2005;435:519–22. · DOI
  3. Ravelli RB, Gigant B, Curmi PA, Jourdain I, Lachkar S, Sobel A, et al. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature. 2004;428:198–202. · DOI
  4. Seveand P, Dumontet C. Is class III beta-tubulin a predictive factor in patients receiving tubulin-binding agents? The Lancet Oncology. 2008;9:168–75. · DOI
  5. Stengel C, Newman SP, Leese MP, Potter BV, Reed MJ, Purohit A. Class III beta-tubulin expression and in vitro resistance to microtubule targeting agents. Br J Cancer. 2010;102:316–24. · DOI
  6. Goto H, Yano S, Zhang H, Matsumori Y, Ogawa H, Blakey DC, et al. Activity of a new vascular targeting agent, ZD6126, in pulmonary metastases by human lung adenocarcinoma in nude mice. Cancer Res. 2002;62:3711–5.
  7. Lippert 3rd JW. Vascular disrupting agents. Bioorg Med Chem. 2007;15:605–15. · DOI
  8. Rustin GJ, Shreeves G, Nathan PD, Gaya A, Ganesan TS, Wang D, et al. A Phase Ib trial of CA4P (combretastatin A-4 phosphate), carboplatin, and paclitaxel in patients with advanced cancer. Br J Cancer. 2010;102:1355–60. · DOI
  9. Kim TJ, Ravoori M, Landen CN, Kamat AA, Han LY, Lu C, et al. Antitumor and antivascular effects of AVE8062 in ovarian carcinoma. Cancer Res. 2007;67:9337–45. · DOI
  10. Pettit GR, Toki B, Herald DL, Verdier-Pinard P, Boyd MR, Hamel E, et al. Antineoplastic agents. 379. Synthesis of phenstatin phosphate. J Med Chem. 1998;41:1688–95. · DOI
  11. Zhang LH, Wu L, Raymon HK, Chen RS, Corral L, Shirley MA, et al. The synthetic compound CC-5079 is a potent inhibitor of tubulin polymerization and tumor necrosis factor-alpha production with antitumor activity. Cancer Res. 2006;66:951–9. · DOI
  12. Bohlinand L, Rosen B. Podophyllotoxin derivatives: drug discovery and development. Drug Discov Today. 1996;1:343–51. · DOI
  13. Kupchan SM, Britton RW, Ziegler MF, Gilmore CJ, Restivo RJ, Bryan RF. Steganacin and steganangin, novel antileukemic lignan lactones from Steganotaenia araliacea. J Am Chem Soc. 1973;95:1335–6. · DOI
  14. Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. Journal of Applied Toxicology: JAT 2011. doi: 10.1002/jat.1753 · DOI
  15. Hamel E. Antimitotic natural products and their interactions with tubulin. Medicinal Research Reviews. 1996;16:207–31. · DOI
  16. Matei D, Schilder J, Sutton G, Perkins S, Breen T, Quon C, et al. Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial. Gynecol Oncol. 2009;115:90–6. · DOI
  17. Pasquier E, Sinnappan S, Munoz MA, Kavallaris M. ENMD-1198, a new analogue of 2-methoxyestradiol, displays both antiangiogenic and vascular-disrupting properties. Mol Cancer Ther. 2010;9:1408–18. · DOI
  18. Hande KR, Hagey A, Berlin J, Cai Y, Meek K, Kobayashi H, et al. The pharmacokinetics and safety of ABT-751, a novel, orally bioavailable sulfonamide antimitotic agent: results of a phase 1 study. Clin Cancer Res. 2006;12:2834–40. · DOI
  19. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, et al. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999;96:5686–91. · DOI
  20. Patterson DM, Rustin GJS, Serradell N, Rosa E, Bolos J. Combretastatin A-4 phosphate. Drugs of the Future. 2007;32:1025–32. · DOI
  21. Rischin D, Bibby DC, Chong G, Kremmidiotis G, Leske AF, Matthews CA, 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. Clin Cancer Res. 2011;17:5152–60. · DOI
  22. Bacher G, Nickel B, Emig P, Vanhoefer U, Seeber S, Shandra A, et al. D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows efficacy toward multidrug-resistant tumor cells, and lacks neurotoxicity. Cancer Res. 2001;61:392–9.
  23. Gourdeau H, Leblond L, Hamelin B, Desputeau C, Dong K, Kianicka I, et al. Antivascular and antitumor evaluation of 2-amino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents. Mol Cancer Ther. 2004;3:1375–84. · DOI
  24. Sirisoma N, Kasibhatla S, Pervin A, Zhang H, Jiang S, Willardsen JA, 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 Med Chem. 2008;51:4771–9. · DOI
  25. Tsimberidou AM, Akerley W, Schabel MC, Hong DS, Uehara C, Chhabra A, et al. Phase I clinical trial of MPC-6827 (Azixa), a microtubule destabilizing agent, in patients with advanced cancer. Mol Cancer Ther. 2010;9:3410–9. · DOI
  26. Burns CJ, Fantino E, Phillips ID, Su S, Harte MF, Bukczynska PE, et al. CYT997: a novel orally active tubulin polymerization inhibitor with potent cytotoxic and vascular disrupting activity in vitro and in vivo. Mol Cancer Ther. 2009;8:3036–45. · DOI
  27. Shiand W, Siemann DW. Preclinical studies of the novel vascular disrupting agent MN-029. Anticancer Res. 2005;25:3899–904.
  28. Ricart AD, Ashton EA, Cooney MM, Sarantopoulos J, Brell JM, Feldman MA, et al. A phase I study of MN-029 (denibulin), a novel vascular-disrupting agent, in patients with advanced solid tumors. Cancer Chemotherapy and Pharmacology. 2011;68:959–70. · DOI
  29. de Ines C, Leynadier D, Barasoain I, Peyrot V, Garcia P, Briand C, et al. Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NSC 613863. Cancer Res. 1994;54:75–84.
  30. Thomas JP, Moore T, Kraut EH, Balcerzak SP, Galloway S, Vandre DD. A phase II study of CI-980 in previously untreated extensive small cell lung cancer: an Ohio State University phase II research consortium study. Cancer Investigation. 2002;20:192–8. · DOI
  31. Yoon JT, Palazzo AF, Xiao D, Delohery TM, Warburton PE, Bruce JN, et al. CP248, a derivative of exisulind, causes growth inhibition, mitotic arrest, and abnormalities in microtubule polymerization in glioma cells. Mol Cancer Ther. 2002;1:393–404.
  32. Sun W, Stevenson JP, Gallo JM, Redlinger M, Haller D, Algazy K, et al. Phase I and pharmacokinetic trial of the proapoptotic sulindac analog CP-461 in patients with advanced cancer. Clin Cancer Res. 2002;8:3100–4.
  33. Tripodi F, Pagliarin R, Fumagalli G, Bigi A, Fusi P, Orsini F, et al. Synthesis and biological evaluation of 1,4-Diaryl-2-azetidinones as specific anticancer agents: activation of adenosine monophosphate activated protein kinase and induction of apoptosis. J Med Chem. 2012;55:2112–24. · DOI
  34. Bai R, Covell DG, Pei XF, Ewell JB, Nguyen NY, Brossi A, et al. Mapping the binding site of colchicinoids on beta -tubulin. 2-Chloroacetyl-2-demethylthiocolchicine covalently reacts predominantly with cysteine 239 and secondarily with cysteine 354. J Biol Chem. 2000;275:40443–52. · DOI
  35. Dorleans A, Gigant B, Ravelli RB, Mailliet P, Mikol V, Knossow M. Variations in the colchicine-binding domain provide insight into the structural switch of tubulin. Proc Natl Acad Sci U S A. 2009;106:13775–9. · DOI
  36. Barbier P, Dorleans A, Devred F, Sanz L, Allegro D, Alfonso C, et al. Stathmin and interfacial microtubule inhibitors recognize a naturally curved conformation of tubulin dimers. J Biol Chem. 2010;285:31672–81. · DOI
  37. Nguyen TL, McGrath C, Hermone AR, Burnett JC, Zaharevitz DW, Day BW, et al. A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach. J Med Chem. 2005;48:6107–16. · DOI
  38. Dutcher SK. The tubulin fraternity: alpha to eta. Curr Opin Cell Biol. 2001;13:49–54. · DOI
  39. Simoni D, Romagnoli R, Baruchello R, Rondanin R, Rizzi M, Pavani MG, et al. Novel combretastatin analogues endowed with antitumor activity. J Med Chem. 2006;49:3143–52. · DOI
  40. Stevenson JP, Rosen M, Sun W, Gallagher M, Haller DG, Vaughn D, et al. Phase I trial of the antivascular agent combretastatin A4 phosphate on a 5-day schedule to patients with cancer: magnetic resonance imaging evidence for altered tumor blood flow. Journal of Clinical Oncology: Official Journal of the American Society of Clinical Oncology. 2003;21:4428–38. · DOI
  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. 2006;49:3033–44. · DOI
  42. Aprile S, Del Grosso E, Tron GC, Grosa G. In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes. Drug Metabolism and Disposition: the Biological Fate of Chemicals. 2007;35:2252–61. · DOI
  43. Gwaltney 2nd SL, Imade HM, Barr KJ, Li Q, Gehrke L, Credo RB, et al. Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents. Bioorganic & Medicinal Chemistry Letters. 2001;11:871–4. · DOI
  44. Fortin S, Wei L, Moreau E, Lacroix J, Cote MF, Petitclerc E, et al. synthesis, biological evaluation, and structure-activity relationships of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates as new tubulin inhibitors mimicking combretastatin A-4. J Med Chem. 2011;54:4559–80. · DOI
  45. Fortin S, Wei L, Moreau E, Lacroix J, Cote MF, Petitclerc E, et al. Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships. European Journal of Medicinal Chemistry. 2011;46:5327–42. · DOI
  46. Simoni D, Romagnoli R, Baruchello R, Rondanin R, Grisolia G, Eleopra M, et al. Novel A-ring and B-ring modified combretastatin A-4 (CA-4) analogues endowed with interesting cytotoxic activity. J Med Chem. 2008;51:6211–5. · DOI
  47. Ohsumi K, Hatanaka T, Fujita K, Nakagawa R, Fukuda Y, Nihei Y, et al. Syntheses and antitumor activity of cis-restricted combretastatins: 5-membered heterocyclic analogues. Bioorganic & Medicinal Chemistry Letters. 1998;8:3153–8. · DOI
  48. Wang L, Woods KW, Li Q, Barr KJ, McCroskey RW, Hannick SM, et al. Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J Med Chem. 2002;45:1697–711. · DOI
  49. Kim Y, Nam NH, You YJ, Ahn BZ. Synthesis and cytotoxicity of 3,4-diaryl-2(5H)-furanones. Bioorganic & Medicinal Chemistry Letters. 2002;12:719–22. · DOI
  50. Nam NH, Kim Y, You YJ, Hong DH, Kim HM, Ahn BZ. Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues. Bioorganic & Medicinal Chemistry Letters. 2002;12:1955–8. · DOI
  51. Nam NH, Kim Y, You YJ, Hong DH, Kim HM, Ahn BZ. Combretoxazolones: synthesis, cytotoxicity and antitumor activity. Bioorganic & Medicinal Chemistry Letters. 2001;11:3073–6. · DOI
  52. Bailly C, Bal C, Barbier P, Combes S, Finet JP, Hildebrand MP, et al. Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. J Med Chem. 2003;46:5437–44. · DOI
  53. Combes S, Barbier P, Douillard S, McLeer-Florin A, Bourgarel-Rey V, Pierson JT, et al. Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. Part 2. J Med Chem. 2011;54:3153–62. · DOI
  54. Tron GC, Pagliai F, Del Grosso E, Genazzani AA, Sorba G. Synthesis and cytotoxic evaluation of combretafurazans. J Med Chem. 2005;48:3260–8. · DOI
  55. Pati HN, Wicks M, Holt HL, Leblanc R, Weisbruch P, Forrest L, et al. Synthesis and biological evaluation of cis-combretastatin analogs and their novel 1,2,3-triazole derivatives. Heterocyclic Commun. 2005;11:117–20.
  56. Simoni D, Grisolia G, Giannini G, Roberti M, Rondanin R, Piccagli L, et al. Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines. J Med Chem. 2005;48:723–36. · DOI
  57. Flynn BL, Flynn GP, Hamel E, Jung MK. The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. Bioorganic & Medicinal Chemistry Letters. 2001;11:2341–3. · DOI
  58. O'Boyle NM, Carr M, Greene LM, Bergin O, Nathwani SM, McCabe T, et al. Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents. J Med Chem. 2010;53:8569–84. · DOI
  59. Romagnoli R, Baraldi PG, Brancale A, Ricci A, Hamel E, Bortolozzi R, et al. Convergent synthesis and biological evaluation of 2-amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents. J Med Chem. 2011;54:5144–53. · DOI
  60. Beale TM, Allwood DM, Bender A, Bond PJ, Brenton JD, Charnock-Jones DS, et al. Xian A-ring dihalogenation increases the cellular activity of combretastatin-templated tetrazoles. ACS Medicinal Chemistry Letters: Ahead of Print, 2012. · DOI
  61. Schobert R, Biersack B, Dietrich A, Effenberger K, Knauer S, Mueller T. 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 Med Chem. 2010;53:6595–602. · DOI
  62. Theeramunkong S, Caldarelli A, Massarotti A, Aprile S, Caprioglio D, Zaninetti R, et al. Regioselective Suzuki coupling of dihaloheteroaromatic compounds as a rapid strategy to synthesize potent rigid combretastatin analogues. J Med Chem. 2011;54:4977–86. · DOI
  63. Furst R, Zupko I, Berenyi A, Ecker GF, Rinner U. Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs. Bioorganic & Medicinal Chemistry Letters. 2009;19:6948–51. · DOI
  64. Hadfield JA, Gaukroger K, Hirst N, Weston AP, Lawrence NJ, McGown AT. Synthesis and evaluation of double bond substituted combretastatins. European Journal of Medicinal Chemistry. 2005;40:529–41. · DOI
  65. Liu T, Cui R, Chen J, Zhang J, He Q, Yang B, et al. 4,5-Diaryl-3-aminopyrazole derivatives as analogs of Combretastatin A-4: synthesis and biological evaluation. Arch Pharm. 2011;344:279–86. · DOI
  66. Akselsen OW, Odlo K, Cheng JJ, Maccari G, Botta M, Hansen TV. Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. Bioorg Med Chem. 2012;20:234–42. · DOI
  67. Xue N, Yang X, Wu R, Chen J, He Q, Yang B, et al. Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents. Bioorg Med Chem. 2008;16:2550–7. · DOI
  68. Ruprich J, Prout A, Dickson J, Younglove B, Nolan L, Baxi K, et al. Design, synthesis and biological testing of cyclohexenone derivatives of combretastatin-A4. Letters in Drug Design & Discovery. 2007;4:144–8. · DOI
  69. Lee L, Davis R, Vanderham J, Hills P, Mackay H, Brown T, et al. 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4. European Journal of Medicinal Chemistry. 2008;43:2011–5. · DOI
  70. Johnson M, Younglove B, Lee L, LeBlanc R, Holt Jr H, Hills P, et al. Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4. Bioorganic & Medicinal Chemistry Letters. 2007;17:5897–901. · DOI
  71. Mateo C, Perez-Melero C, Pelaez R, Medarde M. Stilbenophane analogues of deoxycombretastatin A-4. J Org Chem. 2005;70:6544–7. · DOI
  72. De Martino G, Edler MC, La Regina G, Coluccia A, Barbera MC, Barrow D, et al. New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies. J Med Chem. 2006;49:947–54. · DOI
  73. De Martino G, La Regina G, Coluccia A, Edler MC, Barbera MC, Brancale A, et al. Arylthioindoles, potent inhibitors of tubulin polymerization. J Med Chem. 2004;47:6120–3. · DOI
  74. La Regina G, Sarkar T, Bai R, Edler MC, Saletti R, Coluccia A, 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. 2009;52:7512–27. · DOI
  75. La Regina G, Bai R, Rensen W, Coluccia A, Piscitelli F, Gatti V, 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 Med Chem. 2011;54:8394–406. · DOI
  76. Mahboobi S, Pongratz H, Hufsky H, Hockemeyer J, Frieser M, Lyssenko A, et al. Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents. J Med Chem. 2001;44:4535–53. · DOI
  77. Kuo CC, Hsieh HP, Pan WY, Chen CP, Liou JP, Lee SJ, et al. BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004;64:4621–8. · DOI
  78. Hu CB, Chen CP, Yeh TK, Song JS, Chang CY, Chuu JJ, et al. BPR0C261 is a novel orally active antitumor agent with antimitotic and anti-angiogenic activities. Cancer Science. 2011;102:182–91. · DOI
  79. Li WT, Hwang DR, Chen CP, Shen CW, Huang CL, Chen TW, et al. Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents. J Med Chem. 2003;46:1706–15. · DOI
  80. Nien CY, Chen YC, Kuo CC, Hsieh HP, Chang CY, Wu JS, et al. 5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. J Med Chem. 2010;53:2309–13. · DOI
  81. Liou JP, Wu ZY, Kuo CC, Chang CY, Lu PY, Chen CM, et al. Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors. J Med Chem. 2008;51:4351–5. · DOI
  82. Lee HY, Chang JY, Nien CY, Kuo CC, Shih KH, Wu CH, et al. 5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. Part 2. The impact of bridging groups at position C-2. J Med Chem. 2011;54:8517–25. · DOI
  83. Arthuis M, Pontikis R, Chabot GG, Quentin L, Scherman D, Florent JC. Domino approach to 2-aroyltrimethoxyindoles as novel heterocyclic combretastatin A4 analogues. European Journal of Medicinal Chemistry. 2011;46:95–100. · DOI
  84. Lai MJ, Chang JY, Lee HY, Kuo CC, Lin MH, Hsieh HP, et al. Synthesis and biological evaluation of 1-(4'-Indolyl and 6'-Quinolinyl) indoles as a new class of potent anticancer agents. European Journal of Medicinal Chemistry. 2011;46:3623–9. · DOI
  85. Lai MJ, Kuo CC, Yeh TK, Hsieh HP, Chen LT, Pan WY, et al. Synthesis and structure-activity relationships of 1-benzyl-4,5,6-trimethoxyindoles as a novel class of potent antimitotic agents. ChemMedChem. 2009;4:588–93. · DOI
  86. Xie F, Zhao H, Li D, Chen H, Quan H, Shi X, et al. Synthesis and biological evaluation of 2,4,5-substituted pyrimidines as a new class of tubulin polymerization inhibitors. J Med Chem. 2011;54:3200–5. · DOI
  87. El-Nakkady SS, Hanna MM, Roaiah HM, Ghannam IA. Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives. European Journal of Medicinal Chemistry. 2012;47:387–98. · DOI
  88. Arora S, Wang XI, Keenan SM, Andaya C, Zhang Q, Peng Y, et al. Novel microtubule polymerization inhibitor with potent antiproliferative and antitumor activity. Cancer Res. 2009;69:1910–5. · DOI
  89. Shetty RS, Lee Y, Liu B, Husain A, Joseph RW, Lu Y, et al. Synthesis and pharmacological evaluation of N-(3-(1H-indol-4-yl)-5-(2-methoxyisonicotinoyl)phenyl)methanesulfonamide (LP-261), a potent antimitotic agent. J Med Chem. 2011;54:179–200. · DOI
  90. Li L, Wang HK, Kuo SC, Wu TS, Mauger A, Lin CM, et al. Antitumor agents. 155. Synthesis and biological evaluation of 3',6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents. J Med Chem. 1994;37:3400–7. · DOI
  91. Li L, Wang HK, Kuo SC, Wu TS, Lednicer D, Lin CM, et al. Antitumor agents. 150. 2',3',4',5',5,6,7-substituted 2-phenyl-4-quinolones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. J Med Chem. 1994;37:1126–35. · DOI
  92. Zhang C, Yang N, Yang CH, Ding HS, Luo C, Zhang Y, et al. S9, a novel anticancer agent, exerts its anti-proliferative activity by interfering with both PI3K-Akt-mTOR signaling and microtubule cytoskeleton. PLoS One. 2009;4:e4881. · DOI
  93. Romagnoli R, Baraldi PG, Carrion MD, Lopez Cara C, Preti D, Fruttarolo F, et al. Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization. J Med Chem. 2007;50:2273–7. · DOI
  94. Keller L, Beaumont S, Liu JM, Thoret S, Bignon JS, Wdzieczak-Bakala J, et al. New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: cytotoxic and antitumor activities. J Med Chem. 2008;51:3414–21. · DOI
  95. Pons V, Beaumont S, Dau METH, Iorga BI, Dodd RH. Rigid analogues of antimitotic indolobenzazepinones: new insights into tubulin binding via molecular modeling. ACS Medicinal Chemistry Letters. 2011;2:565–570. · DOI
  96. Boumendjel A, McLeer-Florin A, Champelovier P, Allegro D, Muhammad D, Souard F, et al. A novel chalcone derivative which acts as a microtubule depolymerising agent and an inhibitor of P-gp and BCRP in in-vitro and in-vivo glioblastoma models. BMC Cancer. 2009;9:242. · DOI
  97. Kerr DJ, Hamel E, Jung MK, Flynn BL. The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4. Bioorg Med Chem. 2007;15:3290–8. · DOI
  98. Luo Y, Qiu KM, Lu X, Liu K, Fu J, Zhu HL. Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents. Bioorg Med Chem. 2011;19:4730–8. · DOI
  99. Ruan BF, Lu X, Tang JF, Wei Y, Wang XL, Zhang YB, et al. Synthesis, biological evaluation, and molecular docking studies of resveratrol derivatives possessing chalcone moiety as potential antitubulin agents. Bioorg Med Chem. 2011;19:2688–95. · DOI
  100. Risinger AL, Westbrook CD, Encinas A, Mulbaier M, Schultes CM, Wawro S, et al. ELR510444, a novel microtubule disruptor with multiple mechanisms of action. J Pharmacol Exp Ther. 2011;336:652–60. · DOI
  101. Chang JY, Hsieh HP, Chang CY, Hsu KS, Chiang YF, Chen CM, et al. 7-Aroyl-aminoindoline-1-sulfonamides as a novel class of potent antitubulin agents. J Med Chem. 2006;49:6656–9. · DOI
  102. Liou JP, Hsu KS, Kuo CC, Chang CY, Chang JY. A novel oral indoline-sulfonamide agent, N-[1-(4-methoxybenzenesulfonyl)-2,3-dihydro-1H-indol-7-yl]-isonicotinamide (J30), exhibits potent activity against human cancer cells in vitro and in vivo through the disruption of microtubule. J Pharmacol Exp Ther. 2007;323:398–405. · DOI
  103. Cushman M, He HM, Katzenellenbogen JA, Varma RK, Hamel E, Lin CM, et al. Synthesis of analogs of 2-methoxyestradiol with enhanced inhibitory effects on tubulin polymerization and cancer cell growth. J Med Chem. 1997;40:2323–34. · DOI
  104. Cushman M, Mohanakrishnan AK, Hollingshead M, Hamel E. The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerization. J Med Chem. 2002;45:4748–54. · DOI
  105. Edsall AB, Mohanakrishnan AK, Yang D, Fanwick PE, Hamel E, Hanson AD, et al. Effects of altering the electronics of 2-methoxyestradiol on cell proliferation, on cytotoxicity in human cancer cell cultures, and on tubulin polymerization. J Med Chem. 2004;47:5126–39. · DOI
  106. Agoston GE, Shah JH, Lavallee TM, Zhan X, Pribluda VS, Treston AM. Synthesis and structure-activity relationships of 16-modified analogs of 2-methoxyestradiol. Bioorg Med Chem. 2007;15:7524–37. · DOI
  107. Chander SK, Foster PA, Leese MP, Newman SP, Potter BV, Purohit A, et al. In vivo inhibition of angiogenesis by sulphamoylated derivatives of 2-methoxyoestradiol. Br J Cancer. 2007;96:1368–76. · DOI
  108. Ireson CR, Chander SK, Purohit A, Perera S, Newman SP, Parish D, et al. Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents. Br J Cancer. 2004;90:932–7. · DOI
  109. Jourdan F, Leese MP, Dohle W, Hamel E, Ferrandis E, Newman SP, et al. Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate. J Med Chem. 2010;53:2942–51. · DOI
  110. Nakagawa-Goto K, Chen TH, Peng CY, Bastow KF, Wu JH, Lee KH. Antitumor agents 259. Design, syntheses, and structure-activity relationship study of desmosdumotin C analogs. J Med Chem. 2007;50:3354–8. · DOI
  111. Nakagawa-Goto K, Bastow KF, Chen TH, Morris-Natschke SL, Lee KH. Antitumor agents 260. New desmosdumotin B analogues with improved in vitro anticancer activity. J Med Chem. 2008;51:3297–303. · DOI
  112. Nakagawa-Goto K, Wu PC, Lai CY, Hamel E, Zhu H, Zhang L, et al. Antitumor agents. 284. New desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents. J Med Chem. 2011;54:1244–55. · DOI
  113. Nakagawa-Goto K, Wu PC, Bastow KF, Yang SC, Yu SL, Chen HY, et al. Antitumor agents 283. Further elaboration of desmosdumotin C analogs as potent antitumor agents: activation of spindle assembly checkpoint as possible mode of action. Bioorg Med Chem. 2011;19:1816–22. · DOI
  114. Beutler JA, Cardellina JH II, Lin CM, Hamel E, Cragg GM, Boyd MR. Centaureidin, a cytotoxic flavone from Polymnia fruticosa, inhibits tubulin polymerization. Bioorganic & Medicinal Chemistry Letters. 1993;3:581–4. · DOI
  115. Naik PK, Chatterji BP, Vangapandu SN, Aneja R, Chandra R, Kanteveri S, et al. Rational design, synthesis and biological evaluations of amino-noscapine: a high affinity tubulin-binding noscapinoid. J Comput Aided Mol Des. 2011;25:443–54. · DOI
  116. Hartley RM, Peng J, Fest GA, Dakshanamurthy S, Frantz DE, Brown ML, et al. Polygamain, a new microtubule depolymerizing agent that occupies a unique pharmacophore in the colchicine site. Molecular Pharmacology. 2011. · DOI
  117. Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, et al. Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus. J Antibiot. 1995;48:1382–4. · DOI
  118. Woehlecke H, Osada H, Herrmann A, Lage H. Reversal of breast cancer resistance protein-mediated drug resistance by tryprostatin A. International Journal of Cancer Journal International Du Cancer. 2003;107:721–8. · DOI
  119. Kanoh K, Kohno S, Katada J, Takahashi J, Uno I. (-)-Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization. J Antibiot. 1999;52:134–41. · DOI
  120. Kanzaki H, Yanagisawa S, Kanoh K, Nitoda T. A novel potent cell cycle inhibitor dehydrophenylahistin–enzymatic synthesis and inhibitory activity toward sea urchin embryo. J Antibiot. 2002;55:1042–7. · DOI
  121. Yamazaki Y, Tanaka K, Nicholson B, Deyanat-Yazdi G, Potts B, Yoshida T, et al. Synthesis and Structure-Activity Relationship Study of Antimicrotubule Agents Phenylahistin Derivatives with a Didehydropiperazine-2,5-dione Structure. J Med Chem. 2012;55:1056–71. · DOI
  122. Wipf P, Reeves JT, Balachandran R, Day BW. Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A. J Med Chem. 2002;45:1901–17. · DOI
  123. Wipf P, Reeves JT, Balachandran R, Giuliano KA, Hamel E, Day BW. Synthesis and Biological Evaluation of a Focused Mixture Library of Analogues of the Antimitotic Marine Natural Product Curacin A. J Am Chem Soc. 2000;122:9391–5. · DOI
  124. Ziegelbauer J, Shan B, Yager D, Larabell C, Hoffmann B, Tjian R. Transcription factor MIZ-1 is regulated via microtubule association. Molecular Cell. 2001;8:339–49. · DOI
  125. Bai R, Pei XF, Boye O, Getahun Z, Grover S, Bekisz J, et al. Identification of cysteine 354 of beta-tubulin as part of the binding site for the A ring of colchicine. J Biol Chem. 1996;271:12639–45. · DOI
  126. Combeau C, Provost J, Lancelin F, Tournoux Y, Prod'homme F, Herman F, et al. RPR112378 and RPR115781: two representatives of a new family of microtubule assembly inhibitors. Mol Pharmacol. 2000;57:553–63. · DOI
  127. Bouchon B, Chambon C, Mounetou E, Papon J, Miot-Noirault E, Gaudreault RC, et al. Alkylation of beta-tubulin on Glu 198 by a microtubule disrupter. Mol Pharmacol. 2005;68:1415–22. · DOI
  128. Fortin S, Bouchon B, Chambon C, Lacroix J, Moreau E, Chezal JM, et al. Characterization of the covalent binding of N-phenyl-N'-(2-chloroethyl)ureas to {beta}-tubulin: importance of Glu198 in microtubule stability. J Pharmacol Exp Ther. 2011;336:460–7. · DOI
  129. Prinz H, Schmidt P, Bohm KJ, Baasner S, Muller K, Gerlach M, et al. Phenylimino-10H-anthracen-9-ones as novel antimicrotubule agents-synthesis, antiproliferative activity and inhibition of tubulin polymerization. Bioorg Med Chem. 2011;19:4183–91. · DOI
  130. Kasibhatla S, Gourdeau H, Meerovitch K, Drewe J, Reddy S, Qiu L, et al. Discovery and mechanism of action of a novel series of apoptosis inducers with potential vascular targeting activity. Mol Cancer Ther. 2004;3:1365–74. · DOI
  131. Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grundy C, Labreque D, 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. 4. Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions. J Med Chem. 2008;51:417–23. · DOI
  132. Henderson MC, Shaw YJ, Wang H, Han H, Hurley LH, Flynn G, et al. UA62784, a novel inhibitor of centromere protein E kinesin-like protein. Mol Cancer Ther. 2009;8:36–44. · DOI
  133. Tcherniuk S, Deshayes S, Sarli V, Divita G, Abrieu A. UA62784 Is a cytotoxic inhibitor of microtubules, not CENP-E. Chem Biol. 2011;18:631–41. · DOI
  134. Dalyot-Herman N, Delgado-Lopez F, Gewirtz DA, Gupton JT, Schwartz EL. Interference with endothelial cell function by JG-03-14, an agent that binds to the colchicine site on microtubules. Biochem Pharmacol. 2009;78:1167–77. · DOI
  135. Mooberry SL, Weiderhold KN, Dakshanamurthy S, Hamel E, Banner EJ, Kharlamova A, et al. Identification and characterization of a new tubulin-binding tetrasubstituted brominated pyrrole. Mol Pharmacol. 2007;72:132–40. · DOI
  136. Zhang Z, Meng T, Yang N, Wang W, Xiong B, Chen Y, et al. MT119, a new planar-structured compound, targets the colchicine site of tubulin arresting mitosis and inhibiting tumor cell proliferation. International Journal of Cancer Journal International Du Cancer. 2011;129:214–24. · DOI
  137. Lisowski V, Leonce S, Kraus-Berthier L, Sopkova-de Oliveira Santos J, Pierre A, Atassi G, et al. Design, synthesis, and evaluation of novel thienopyrrolizinones as antitubulin agents. J Med Chem. 2004;47:1448–64. · DOI
  138. Leoni LM, Hamel E, Genini D, Shih H, Carrera CJ, Cottam HB, et al. Indanocine, a microtubule-binding indanone and a selective inducer of apoptosis in multidrug-resistant cancer cells. J Natl Cancer Inst. 2000;92:217–24. · DOI
  139. Liberatore AM, Coulomb H, Pons D, Dutruel O, Kasprzyk PG, Carlson M, et al. IRC-083927 is a new tubulin binder that inhibits growth of human tumor cells resistant to standard tubulin-binding agents. Mol Cancer Ther. 2008;7:2426–34. · DOI
  140. Wasylyk C, Zheng H, Castell C, Debussche L, Multon MC, Wasylyk B. Inhibition of the Ras-Net (Elk-3) pathway by a novel pyrazole that affects microtubules. Cancer Res. 2008;68:1275–83. · DOI
  141. Shin KD, Yoon YJ, Kang YR, Son KH, Kim HM, Kwon BM, et al. KRIBB3, a novel microtubule inhibitor, induces mitotic arrest and apoptosis in human cancer cells. Biochem Pharmacol. 2008;75:383–94. · DOI
  142. Szczepankiewicz BG, Liu G, Jae HS, Tasker AS, Gunawardana IW, von Geldern TW, et al. New antimitotic agents with activity in multi-drug-resistant cell lines and in vivo efficacy in murine tumor models. J Med Chem. 2001;44:4416–30. · DOI
  143. Tahir SK, Han EK, Credo B, Jae HS, Pietenpol JA, Scatena CD, et al. A-204197, a new tubulin-binding agent with antimitotic activity in tumor cell lines resistant to known microtubule inhibitors. Cancer Res. 2001;61:5480–5.
  144. Li Q, Woods KW, Claiborne A, Gwaltney 2nd SL, Barr KJ, Liu G, et al. Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumor agent. Bioorganic & Medicinal Chemistry Letters. 2002;12:465–9. · DOI
  145. Tahir SK, Nukkala MA, Zielinski Mozny NA, Credo RB, Warner RB, Li Q, et al. Biological activity of A-289099: an orally active tubulin-binding indolyloxazoline derivative. Mol Cancer Ther. 2003;2:227–33.
  146. Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. Antitumor activity of new substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones: selectivity against colon tumor cells and effect on cell cycle-related events. J Med Chem. 2008;51:7508–13. · DOI
  147. Andreani A, Granaiola M, Locatelli A, Morigi R, Rambaldi M, Varoli L, et al. Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues: synthesis, cytotoxic activity, and study of the mechanism of action (1). J Med Chem. 2012. · DOI
  148. Edsall AB, Agoston GE, Treston AM, Plum SM, McClanahan RH, Lu TS, et al. Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate. J Med Chem. 2007;50:6700–5. · DOI
  149. Rubenstein SM, Baichwal V, Beckmann H, Clark DL, Frankmoelle W, Roche D, et al. Hydrophilic, pro-drug analogues of T138067 are efficacious in controlling tumor growth in vivo and show a decreased ability to cross the blood brain barrier. J Med Chem. 2001;44:3599–605. · DOI
  150. Crielaard BJ, van der Wal S, Lammers T, Le HT, Hennink WE, Schiffelers RM, et al. A polymeric colchicinoid prodrug with reduced toxicity and improved efficacy for vascular disruption in cancer therapy. International Journal of Nanomedicine. 2011;6:2697–703. · DOI
  151. Crielaard BJ, van der Wal S, Le HT, Bode AT, Lammers T, Hennink WE, et al. Liposomes as carriers for colchicine-derived prodrugs: Vascular disrupting nanomedicines with tailorable drug release kinetics. European Journal of Pharmaceutical Sciences: Official Journal of the European Federation for Pharmaceutical Sciences. 2012;45:429–35. · DOI
  152. Lu Y, Li CM, Wang Z, Ross 2nd CR, Chen J, Dalton JT, et al. Discovery of 4-substituted methoxybenzoyl-aryl-thiazole as novel anticancer agents: synthesis, biological evaluation, and structure-activity relationships. J Med Chem. 2009;52:1701–11. · DOI
  153. Li CM, Wang Z, Lu Y, Ahn S, Narayanan R, Kearbey JD, et al. Biological activity of 4-substituted methoxybenzoyl-aryl-thiazole: an active microtubule inhibitor. Cancer Res. 2011;71:216–24. · DOI
  154. Li F, Lu Y, Li W, Miller DD, Mahato RI. Synthesis, formulation and in vitro evaluation of a novel microtubule destabilizer, SMART-100. Journal of Controlled Release: Official Journal of the Controlled Release Society. 2010;143:151–8. · DOI
  155. Chen J, Wang Z, Li CM, Lu Y, Vaddady PK, Meibohm B, et al. Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents. J Med Chem. 2010;53:7414–27. · DOI
  156. Babu B, Lee M, Lee L, Strobel R, Brockway O, Nickols A, et al. Acetyl analogs of combretastatin A-4: synthesis and biological studies. Bioorg Med Chem. 2011;19:2359–67. · DOI
  157. Lee M, Brockway O, Dandavati A, Tzou S, Sjoholm R, Satam V, et al. A novel class of trans-methylpyrazoline analogs of combretastatins: synthesis and in-vitro biological testing. European Journal of Medicinal Chemistry. 2011;46:3099–104. · DOI
  158. Gangjee A, Zhao Y, Hamel E, Westbrook C, Mooberry SL. Synthesis and biological activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimi din-4-aminium chloride as potent cytotoxic antitubulin agents. J Med Chem. 2011;54:6151–5. · DOI

Cited by

Sorted by citations

See all 709

Metadata

Authors
Lu, Y., Chen, J., Xiao, M., Li, W., & Miller, D. D.
Venue
Pharmaceutical Research
Publisher
Springer Science and Business Media LLC
Published
2012-07-20
Volume
29
Issue
11
Pages
2943-2971
ISSN
  • 0724-8741
  • 1573-904X
DOI
10.1007/s11095-012-0828-z
PMC
PMC3667160
Cited by
709
References
1
Language
en
Licence
www.springer.com/tdm (tdm)

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review