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Journal articles on the topic 'Tubulin polymerization inhibitors'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Silva-García, Edna M., Carlos M. Cerda-García-Rojas, Rosa E. del Río, and Pedro Joseph-Nathan. "Parvifoline Derivatives as Tubulin Polymerization Inhibitors." Journal of Natural Products 82, no. 4 (2019): 840–49. http://dx.doi.org/10.1021/acs.jnatprod.8b00860.

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2

De Martino, Gabriella, Giuseppe La Regina, Antonio Coluccia, et al. "Arylthioindoles, Potent Inhibitors of Tubulin Polymerization." Journal of Medicinal Chemistry 47, no. 25 (2004): 6120–23. http://dx.doi.org/10.1021/jm049360d.

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3

Inatsuki, Shunsuke, Tomomi Noguchi, Hiroyuki Miyachi, et al. "Tubulin-polymerization inhibitors derived from thalidomide." Bioorganic & Medicinal Chemistry Letters 15, no. 2 (2005): 321–25. http://dx.doi.org/10.1016/j.bmcl.2004.10.072.

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4

Liu, Xu, Xiao-Jing Pang, Yuan Liu, et al. "Discovery of Novel Diarylamide N-Containing Heterocyclic Derivatives as New Tubulin Polymerization Inhibitors with Anti-Cancer Activity." Molecules 26, no. 13 (2021): 4047. http://dx.doi.org/10.3390/molecules26134047.

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Tubulin has been regarded as an attractive and successful molecular target in cancer therapy and drug discovery. Vicinal diaryl is a simple scaffold found in many colchicine site tubulin inhibitors, which is also an important pharmacophoric point of tubulin binding and anti-cancer activity. As the continuation of our research work on colchicine binding site tubulin inhibitors, we designed and synthesized a series of diarylamide N-containing heterocyclic derivatives by the combination of vicinal diaryl core and N-containing heterocyclic skeletons into one hybrid though proper linkers. Among of

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5

Ahsan, Mohamed Jawed, Arun Choupra, Rakesh Kumar Sharma, et al. "Rationale Design, Synthesis, Cytotoxicity Evaluation, and Molecular Docking Studies of 1,3,4-oxadiazole Analogues." Anti-Cancer Agents in Medicinal Chemistry 18, no. 1 (2018): 121–38. http://dx.doi.org/10.2174/1871520617666170419124702.

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Background: 1,3,4-Oxadiazole heterocycles possess a broad spectrum of biological activities. They were reported as potent cytotoxic agents and tubulin inhibitors; hence it is of great interest to explore new oxadiazoles as cytotoxic agents targeting tubulin polymerization. Objective: Two new series of oxadiazoles (5a-h and 12a-h) were synthesized, structurally related to the heterocyclic linked aryl core of IMC-038525, NSC 776715, and NSC 776716, with further modification by incorporating methylene linker. Method: The 2,5-disubstituted-1,3,4-oxadiazoles (5a-h and 12a-h) were synthesized by ref

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6

Sahakyan, H. K., G. G. Arakelov, and K. B. Nazaryan. "In silico Search for Tubulin Polymerization Inhibitors." Molecular Biology 52, no. 4 (2018): 604–8. http://dx.doi.org/10.1134/s0026893318040179.

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7

Zhang, Qiang, Youyi Peng, Xin I. Wang, Susan M. Keenan, Sonia Arora, and William J. Welsh. "Highly Potent Triazole-Based Tubulin Polymerization Inhibitors." Journal of Medicinal Chemistry 50, no. 4 (2007): 749–54. http://dx.doi.org/10.1021/jm061142s.

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8

Lee, Sang-Choon, Sang-Heon Kim, Rachel A. Hoffmeister, Moon-Young Yoon, and Sung-Kun Kim. "Novel Peptide-Based Inhibitors for Microtubule Polymerization in Phytophthora capsici." International Journal of Molecular Sciences 20, no. 11 (2019): 2641. http://dx.doi.org/10.3390/ijms20112641.

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The plant disease Phytophthora blight, caused by the oomycete pathogen Phytophthora capsici, is responsible for major economic losses in pepper production. Microtubules have been an attractive target for many antifungal agents as they are involved in key cellular events such as cell proliferation, signaling, and migration in eukaryotic cells. In order to design a novel biocompatible inhibitor, we screened and identified inhibitory peptides against alpha- and beta-tubulin of P. capsici using a phage display method. The identified peptides displayed a higher binding affinity (nanomolar range) an

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9

Yan, Wei, Tao Yang, Jianhong Yang, et al. "SKLB060 Reversibly Binds to Colchicine Site of Tubulin and Possesses Efficacy in Multidrug-Resistant Cell Lines." Cellular Physiology and Biochemistry 47, no. 2 (2018): 489–504. http://dx.doi.org/10.1159/000489983.

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Background/Aims: Many tubulin inhibitors are in clinical use as anti-cancer drugs. In our previous study, a novel series of 4-substituted coumarins derivatives were identified as novel tubulin inhibitors. Here, we report the anti-cancer activity and underlying mechanism of one of the 4-substituted coumarins derivatives (SKLB060). Methods: The anti-cancer activity of SKLB060 was tested on 13 different cancer cell lines and four xenograft cancer models. Immunofluorescence staining, cell cycle analysis, and tubulin polymerization assay were employed to study the inhibition of tubulin. N, N ′-Ethy

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10

Xian, Jinghong, Faqian Bu, Yuxi Wang, et al. "A Rationale for Drug Design Provided by Co-Crystal Structure of IC261 in Complex with Tubulin." Molecules 26, no. 4 (2021): 946. http://dx.doi.org/10.3390/molecules26040946.

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Microtubules composed of α/β tubulin heterodimers are an essential part of the cytoskeleton of eukaryotic cells and are widely regarded as targets for cancer chemotherapy. IC261, which is discovered as an ATP-competitive inhibitor of serine/threonine-specific casein kinase 1 (CK1), has shown its inhibitory activity on microtubule polymerization in recent studies. However, the structural information of the interaction between tubulin and IC261 is still unclear. Here, we provided a high-resolution (2.85 Å) crystal structure of tubulin and IC261 complex, revealed the intermolecular interaction be

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11

Subba Rao, A. V., Bala Bhaskara Rao, Satish Sunkari, Siddiq Pasha Shaik, Bajee Shaik, and Ahmed Kamal. "2-Arylaminobenzothiazole-arylpropenone conjugates as tubulin polymerization inhibitors." MedChemComm 8, no. 5 (2017): 924–41. http://dx.doi.org/10.1039/c6md00562d.

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12

Zhang, Shun, Baijiao An, Jiayan Li, et al. "Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7404–10. http://dx.doi.org/10.1039/c7ob01655g.

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Sixteen new selenium-containing indole chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Compound 25b exhibited the most potent antiproliferative activities and effectively inhibited tubulin polymerization (IC<sub>50</sub> = 2.1 ± 0.27 μM).

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13

Marzaro, Giovanni, Antonio Coluccia, Alessandro Ferrarese, et al. "Discovery of Biarylaminoquinazolines as Novel Tubulin Polymerization Inhibitors." Journal of Medicinal Chemistry 57, no. 11 (2014): 4598–605. http://dx.doi.org/10.1021/jm500034j.

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14

Kaur, Ramandeep, Gurneet Kaur, Rupinder Kaur Gill, Richard Soni, and Jitender Bariwal. "Recent developments in tubulin polymerization inhibitors: An overview." European Journal of Medicinal Chemistry 87 (November 2014): 89–124. http://dx.doi.org/10.1016/j.ejmech.2014.09.051.

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15

Bukhari, Syed Nasir Abbas, Gajjela Bharath Kumar, Hrishikesh Mohan Revankar, and Hua-Li Qin. "Development of combretastatins as potent tubulin polymerization inhibitors." Bioorganic Chemistry 72 (June 2017): 130–47. http://dx.doi.org/10.1016/j.bioorg.2017.04.007.

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16

Kamal, Ahmed, M. Kashi Reddy, Thokhir B. Shaik, et al. "Synthesis of terphenyl benzimidazoles as tubulin polymerization inhibitors." European Journal of Medicinal Chemistry 50 (April 2012): 9–17. http://dx.doi.org/10.1016/j.ejmech.2012.01.004.

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17

Li, Zhongping, Lingling Ma, Chengyong Wu, et al. "The Structure of MT189-Tubulin Complex Provides Insights into Drug Design." Letters in Drug Design & Discovery 16, no. 9 (2019): 1069–73. http://dx.doi.org/10.2174/1570180816666181122122655.

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Background: Drugs that interfere with microtubule dynamics are used widely in cancer chemotherapy. Microtubules are composed of αβ-tubulin heterodimers, and the colchicine binding site of tubulin is an important pocket for designing tubulin polymerization inhibitors. We have previously designed and synthesized a series of colchicine binding site inhibitors (CBSIs). However, these compounds showed no anticancer activity in vivo. Then, we have used a deconstruction approach to obtain a new derivative MT189, which showed in vivo anticancer activity. Methods: We crystallized a protein complex incl

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18

Prinz, Helge. "Recent advances in the field of tubulin polymerization inhibitors." Expert Review of Anticancer Therapy 2, no. 6 (2002): 695–708. http://dx.doi.org/10.1586/14737140.2.6.695.

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19

Kumar, Sunil, Samir Mehndiratta, Kunal Nepali, et al. "Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors." Organic and Medicinal Chemistry Letters 3, no. 1 (2013): 3. http://dx.doi.org/10.1186/2191-2858-3-3.

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20

Fang, Zhenglai, Yunlong Song, Taradas Sarkar, et al. "Stereoselective Synthesis of 3,3-Diarylacrylonitriles as Tubulin Polymerization Inhibitors." Journal of Organic Chemistry 73, no. 11 (2008): 4241–44. http://dx.doi.org/10.1021/jo800428b.

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21

Herdman, Christine A., Laxman Devkota, Chen-Ming Lin, et al. "Structural interrogation of benzosuberene-based inhibitors of tubulin polymerization." Bioorganic & Medicinal Chemistry 23, no. 24 (2015): 7497–520. http://dx.doi.org/10.1016/j.bmc.2015.10.012.

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22

Chuang, Hsun-Yueh, Jang-Yang Chang, Mei-Jung Lai, et al. "2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors." ChemMedChem 6, no. 3 (2011): 450–56. http://dx.doi.org/10.1002/cmdc.201000479.

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23

Srikanth, P. S., V. Lakshma Nayak, Korrapati Suresh Babu, G. Bharath Kumar, A. Ravikumar, and Ahmed Kamal. "2-Anilino-3-Aroylquinolines as Potent Tubulin Polymerization Inhibitors." ChemMedChem 11, no. 18 (2016): 2050–62. http://dx.doi.org/10.1002/cmdc.201600259.

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24

Maguire, Casey J., Zhi Chen, Vani P. Mocharla, et al. "Synthesis of dihydronaphthalene analogues inspired by combretastatin A-4 and their biological evaluation as anticancer agents." MedChemComm 9, no. 10 (2018): 1649–62. http://dx.doi.org/10.1039/c8md00322j.

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25

An, Baijiao, Shun Zhang, Jun Yan, Ling Huang, and Xingshu Li. "Synthesis, in vitro and in vivo evaluation of new hybrids of millepachine and phenstatin as potent tubulin polymerization inhibitors." Organic & Biomolecular Chemistry 15, no. 4 (2017): 852–62. http://dx.doi.org/10.1039/c6ob02507b.

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26

Lila, Thomas, Thomas E. Renau, Lori Wilson, et al. "Molecular Basis for Fungal Selectivity of Novel Antimitotic Compounds." Antimicrobial Agents and Chemotherapy 47, no. 7 (2003): 2273–82. http://dx.doi.org/10.1128/aac.47.7.2273-2282.2003.

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ABSTRACT Compounds that selectively disrupt fungal mitosis have proven to be effective in controlling agricultural pests, but no specific mitotic inhibitor is available for the treatment of systemic mycoses in mammalian hosts. In an effort to identify novel mitotic inhibitors, we used a cell-based screening strategy that exploited the hypersensitivity of a yeast α-tubulin mutant strain to growth inhibition by antimitotic agents. The compounds identified inhibited yeast nuclear division and included one structural class of compounds shown to be fungus specific. MC-305,904 and structural analogs

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27

Sunil, Dhanya, and Pooja R. Kamath. "Indole based Tubulin Polymerization Inhibitors: An Update on Recent Developments." Mini-Reviews in Medicinal Chemistry 16, no. 18 (2016): 1470–99. http://dx.doi.org/10.2174/1389557516666160505115324.

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28

Kokoshka, Jerry M., Chris M. Ireland, and Louis R. Barrows. "Cell-Based Screen for Identification of Inhibitors of Tubulin Polymerization." Journal of Natural Products 59, no. 12 (1996): 1179–82. http://dx.doi.org/10.1021/np960144k.

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29

Nien, Chih-Ying, Yun-Ching Chen, Ching-Chuan Kuo, et al. "5-Amino-2-Aroylquinolines as Highly Potent Tubulin Polymerization Inhibitors." Journal of Medicinal Chemistry 53, no. 5 (2010): 2309–13. http://dx.doi.org/10.1021/jm900685y.

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30

Weigt, Mathias, and Michael Wiese. "A Comparative Molecular Field Analysis of Inhibitors of Tubulin Polymerization." Quantitative Structure-Activity Relationships 19, no. 2 (2000): 142–48. http://dx.doi.org/10.1002/1521-3838(200004)19:2<142::aid-qsar142>3.0.co;2-0.

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31

Kamal, Ahmed, M. Kashi Reddy, Thokhir B. Shaik, et al. "ChemInform Abstract: Synthesis of Terphenyl Benzimidazoles as Tubulin Polymerization Inhibitors." ChemInform 43, no. 33 (2012): no. http://dx.doi.org/10.1002/chin.201233139.

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32

Brancale, Andrea, and Romano Silvestri. "Indole, a core nucleus for potent inhibitors of tubulin polymerization." Medicinal Research Reviews 27, no. 2 (2007): 209–38. http://dx.doi.org/10.1002/med.20080.

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33

Aoyama, Hiroshi, Tomomi Noguchi, Takashi Misawa, et al. "Development of Tubulin-Polymerization Inhibitors Based on the Thalidomide Skeleton." CHEMICAL & PHARMACEUTICAL BULLETIN 55, no. 6 (2007): 944–49. http://dx.doi.org/10.1248/cpb.55.944.

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34

Spanò, Virginia, Marzia Pennati, Barbara Parrino, et al. "[1,2]Oxazolo[5,4- e ]isoindoles as promising tubulin polymerization inhibitors." European Journal of Medicinal Chemistry 124 (November 2016): 840–51. http://dx.doi.org/10.1016/j.ejmech.2016.09.013.

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35

Sankara Rao, N., V. Lakshma Nayak, A. V. Subba Rao, et al. "Arylcinnamido-propionone conjugates as tubulin polymerization inhibitors and apoptotic inducers." Arabian Journal of Chemistry 12, no. 8 (2019): 4740–55. http://dx.doi.org/10.1016/j.arabjc.2016.07.014.

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36

Kamal, Ahmed, G. Bharath Kumar, Sowjanya Polepalli, et al. "Design and Synthesis of Aminostilbene-Arylpropenones as Tubulin Polymerization Inhibitors." ChemMedChem 9, no. 11 (2014): 2565–79. http://dx.doi.org/10.1002/cmdc.201402256.

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37

Zhang, Shun, Baijiao An, Jun Yan, Ling Huang, and Xingshu Li. "The synthesis and evaluation of new benzophenone derivatives as tubulin polymerization inhibitors." RSC Advances 6, no. 91 (2016): 88453–62. http://dx.doi.org/10.1039/c6ra16948a.

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Inspired by the potent inhibition activity of phenstatin and millepachine against cancer cell growth, a series of new benzophenone derivatives were synthesized and evaluated as tubulin polymerization inhibitors.

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38

Qin, Hua-Li, Zhen-Peng Shang, Ibrahim Jantan, et al. "Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents." RSC Advances 5, no. 57 (2015): 46330–38. http://dx.doi.org/10.1039/c5ra02995c.

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39

Wang, Yan-Ting, Ya-Juan Qin, Ya-Liang Zhang, et al. "Synthesis, biological evaluation, and molecular docking studies of novel chalcone oxime derivatives as potential tubulin polymerization inhibitors." RSC Adv. 4, no. 61 (2014): 32263–75. http://dx.doi.org/10.1039/c4ra03803g.

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Compounds of novel chalcone oxime derivatives containing different substituent groups were designed, synthesized and evaluated for the inhibitory activity against tubulin polymerization and cancer cell inhibitory activity.

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40

Saravani, Farhad, Ebrahim Saeedian Moghadam, Hafezeh Salehabadi, et al. "Synthesis, Anti-proliferative Evaluation, and Molecular Docking Studies of 3-(alkylthio)-5,6-diaryl-1,2,4-triazines as Tubulin Polymerization Inhibitors." Letters in Drug Design & Discovery 16, no. 11 (2019): 1194–201. http://dx.doi.org/10.2174/1570180815666180727114216.

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Background: The role of microtubules in cell division and signaling, intercellular transport, and mitosis has been well known. Hence, they have been targeted for several anti-cancer drugs. Methods: A series of 3-(alkylthio)-5,6-diphenyl-1,2,4-triazines were prepared and evaluated for their cytotoxic activities in vitro against three human cancer cell lines; human colon carcinoma cells HT-29, human breast adenocarcinoma cell line MCF-7, human Caucasian gastric adenocarcinoma cell line AGS as well as fibroblast cell line NIH-3T3 by MTT assay. Docking simulation was performed to insert these comp

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41

Lien, Vegard Torp, Dag Erlend Olberg, Jo Klaveness, and Carl Henrik Görbitz. "Crystal structure of 6,7-dimethoxy-1-(4-nitrophenyl)quinolin-4(1H)-one: a molecular scaffold for potential tubulin polymerization inhibitors." Acta Crystallographica Section E Crystallographic Communications 73, no. 3 (2017): 441–44. http://dx.doi.org/10.1107/s2056989017002948.

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The protein tubulin is central for maintaining normal cellular processes, and molecules interfering with the tubulin dynamics have potential in the treatment of cancerous diseases. The title compound, C17H14N2O5, was prepared as a lead compound in a project dedicated to the development of therapeutic agents binding to the colchicine binding site on tubulin, thereby interfering with the cell division in cancer cells. It holds many of the main structural characteristics for colchicine binding and has the potential for further modification and functionalization. In the title molecule, the benzene

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42

Miao, Ting-Ting, Xu-Bing Tao, Dong-Dong Li, et al. "Synthesis and biological evaluation of 2-aryl-benzimidazole derivatives of dehydroabietic acid as novel tubulin polymerization inhibitors." RSC Advances 8, no. 31 (2018): 17511–26. http://dx.doi.org/10.1039/c8ra02078g.

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43

Patil, Shivaputra A., Renukadevi Patil, and Duane D. Miller. "Indole molecules as inhibitors of tubulin polymerization: potential new anticancer agents." Future Medicinal Chemistry 4, no. 16 (2012): 2085–115. http://dx.doi.org/10.4155/fmc.12.141.

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44

Spanò, Virginia, Marilia Barreca, Roberta Rocca, et al. "Insight on [1,3]thiazolo[4,5-e]isoindoles as tubulin polymerization inhibitors." European Journal of Medicinal Chemistry 212 (February 2021): 113122. http://dx.doi.org/10.1016/j.ejmech.2020.113122.

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45

Kamal, Ahmed, P. S. Srikanth, M. V. P. S. Vishnuvardhan, et al. "Combretastatin linked 1,3,4-oxadiazole conjugates as a Potent Tubulin Polymerization inhibitors." Bioorganic Chemistry 65 (April 2016): 126–36. http://dx.doi.org/10.1016/j.bioorg.2016.02.007.

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46

Coluccia, Antonio, Davide Sabbadin, and Andrea Brancale. "Molecular modelling studies on Arylthioindoles as potent inhibitors of tubulin polymerization." European Journal of Medicinal Chemistry 46, no. 8 (2011): 3519–25. http://dx.doi.org/10.1016/j.ejmech.2011.05.020.

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47

Kamal, Ahmed, T. Srinivasa Reddy, Sowjanya Polepalli, et al. "Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors." Bioorganic & Medicinal Chemistry 22, no. 19 (2014): 5466–75. http://dx.doi.org/10.1016/j.bmc.2014.07.031.

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48

Yanagawa, Tomonori, Tomomi Noguchi, Hiroyuki Miyachi, Hisayoshi Kobayashi, and Yuichi Hashimoto. "Tubulin polymerization inhibitors with a fluorinated phthalimide skeleton derived from thalidomide." Bioorganic & Medicinal Chemistry Letters 16, no. 18 (2006): 4748–51. http://dx.doi.org/10.1016/j.bmcl.2006.06.091.

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49

Dileep Kumar, G., B. Siva, K. Bharathi, et al. "Synthesis and biological evaluation of Schizandrin derivatives as tubulin polymerization inhibitors." Bioorganic & Medicinal Chemistry Letters 30, no. 16 (2020): 127354. http://dx.doi.org/10.1016/j.bmcl.2020.127354.

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50

Yang, Jianhong, Yong Li, Wei Yan та ін. "Covalent modification of Cys-239 in β-tubulin by small molecules as a strategy to promote tubulin heterodimer degradation". Journal of Biological Chemistry 294, № 20 (2019): 8161–70. http://dx.doi.org/10.1074/jbc.ra118.006325.

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Clinical microtubule-targeting drugs are functionally divided into microtubule-destabilizing and microtubule-stabilizing agents. Drugs from both classes achieve microtubule inhibition by binding different sites on tubulin and inhibiting or promoting polymerization with no concomitant effects on the protein levels of tubulin heterodimers. Here, we have identified a series of small molecules with diverse structures potentially representing a third class of novel tubulin inhibitors that promote degradation by covalent binding to Cys-239 of β-tubulin. The small molecules highlighted in this study

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