Tubulin-Interactive Natural Products as Anticancer Agents (1)
Abstract
This review provides an overview of the discovery, structures, and biological activities of anticancer natural products that act by inhibiting or promoting the assembly of tubulin to microtubules. The emphasis is on providing recent information on those compounds in clinical use or in advanced clinical trials. The vinca alkaloids, the combretastatins, NPI-2358, the halichondrin B analogue eribulin, dolastatin 10, noscapine, hemiasterlin, and rhizoxin are discussed as tubulin polymerization inhibitors, while the taxanes and the epothilones are the major classes of tubulin polymerization promoters presented, with brief treatments of discodermolide, eleutherobin, and laulimalide. The challenges and future directions of tubulin-interactive natural products-based drug discovery programs are also discussed briefly.
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- Blake A. Winn, Laxman Devkota, Bunnarack Kuch, Matthew T. MacDonough, Tracy E. Strecker, Yifan Wang, Zhe Shi, Jeni L. Gerberich, Deboprosad Mondal, Alejandro J. Ramirez, Ernest Hamel, David J. Chaplin, Peter Davis, Ralph P. Mason, Mary Lynn Trawick, Kevin G. Pinney. Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated Hypoxia. Journal of Natural Products 2020, 83 (4) , 937-954. https://doi.org/10.1021/acs.jnatprod.9b00773
- Lucero Martínez-Fructuoso, Rogelio Pereda-Miranda, Daniel Rosas-Ramírez, Mabel Fragoso-Serrano, Carlos M. Cerda-García-Rojas, Aline Soares da Silva, Gilda Guimarães Leitão, Suzana Guimarães Leitão. Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2H-pyran-2-ones from Hyptis Species and Their Molecular Docking to α-Tubulin. Journal of Natural Products 2019, 82 (3) , 520-531. https://doi.org/10.1021/acs.jnatprod.8b00908
- Fredrick O. Ojike, Nathalie Lavignac, Maxwell A. Casely-Hayford. Synthesis and in Vitro Bioactivity of Polyunsaturated Fatty Acid Conjugates of Combretastatin A-4. Journal of Natural Products 2018, 81 (9) , 2101-2105. https://doi.org/10.1021/acs.jnatprod.7b01062
- Ermias Mekuria Addo, Hee-Byung Chai, Ariaya Hymete, Mariamawit Yonathan Yeshak, Carla Slebodnick, David G. I. Kingston, and L. Harinantenaina Rakotondraibe . Antiproliferative Constituents of the Roots of Ethiopian Podocarpus falcatus and Structure Revision of 2α-Hydroxynagilactone F and Nagilactone I. Journal of Natural Products 2015, 78 (4) , 827-835. https://doi.org/10.1021/np501062f
- Yuliya V. Voitovich, Ekaterina S. Shegravina, Nikolay S. Sitnikov, Vladimir I. Faerman, Valery V. Fokin, Hans-Gunther Schmalz, Sebastien Combes, Diane Allegro, Pascal Barbier, Irina P. Beletskaya, Elena V. Svirshchevskaya, and Alexey Yu. Fedorov . Synthesis and Biological Evaluation of Furanoallocolchicinoids. Journal of Medicinal Chemistry 2015, 58 (2) , 692-704. https://doi.org/10.1021/jm501678w
- Madhu Aeluri, Srinivas Chamakuri, Bhanudas Dasari, Shiva Krishna Reddy Guduru, Ravikumar Jimmidi, Srinivas Jogula, and Prabhat Arya . Small Molecule Modulators of Protein–Protein Interactions: Selected Case Studies. Chemical Reviews 2014, 114 (9) , 4640-4694. https://doi.org/10.1021/cr4004049
- Angel E. Bañuelos-Hernández, José Alberto Mendoza-Espinoza, Rogelio Pereda-Miranda, and Carlos M. Cerda-García-Rojas . Studies of (−)-Pironetin Binding to α-Tubulin: Conformation, Docking, and Molecular Dynamics. The Journal of Organic Chemistry 2014, 79 (9) , 3752-3764. https://doi.org/10.1021/jo500420j
- Ludger A. Wessjohann, Günther O. Scheid, Uwe Eichelberger, and Sumaira Umbreen . Total Synthesis of Epothilone D: The Nerol/Macroaldolization Approach. The Journal of Organic Chemistry 2013, 78 (21) , 10588-10595. https://doi.org/10.1021/jo401355r
- Dmitry V. Tsyganov, Leonid D. Konyushkin, Irina B. Karmanova, Sergei I. Firgang, Yuri A. Strelenko, Marina N. Semenova, Alex S. Kiselyov, and Victor V. Semenov . cis-Restricted 3-Aminopyrazole Analogues of Combretastatins: Synthesis from Plant Polyalkoxybenzenes and Biological Evaluation in the Cytotoxicity and Phenotypic Sea Urchin Embryo Assays. Journal of Natural Products 2013, 76 (8) , 1485-1491. https://doi.org/10.1021/np400310m
- Tsai-Yuan Chang, Yun-Peng Tu, Win-Yin Wei, Hsiang Yu Chen, Chih-Shang Chen, Ying-Shuan E. Lee, Jiann-Jyh Huang, and Chin-Kang Sha . Synthesis and Antiproliferative Activities of Ottelione A Analogues. ACS Medicinal Chemistry Letters 2012, 3 (12) , 1075-1080. https://doi.org/10.1021/ml300283f
- Anatoliy M. Shestopalov, Yuri M. Litvinov, Lyudmila A. Rodinovskaya, Oleg R. Malyshev, Marina N. Semenova, and Victor V. Semenov . Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity. ACS Combinatorial Science 2012, 14 (8) , 484-490. https://doi.org/10.1021/co300062e
- Romeo Romagnoli, Pier Giovanni Baraldi, Maria Kimatrai Salvador, Delia Preti, Mojgan Aghazadeh Tabrizi, Andrea Brancale, Xian-Hua Fu, Jun Li, Su-Zhan Zhang, Ernest Hamel, Roberta Bortolozzi, Elena Porcù, Giuseppe Basso, and Giampietro Viola . Discovery and Optimization of a Series of 2-Aryl-4-Amino-5-(3′,4′,5′-trimethoxybenzoyl)Thiazoles as Novel Anticancer Agents. Journal of Medicinal Chemistry 2012, 55 (11) , 5433-5445. https://doi.org/10.1021/jm300388h
- Romeo Romagnoli, Pier Giovanni Baraldi, Maria Kimatrai Salvador, Delia Preti, Mojgan Aghazadeh Tabrizi, Andrea Brancale, Xian-Hua Fu, Jun Li, Su-Zhan Zhang, Ernest Hamel, Roberta Bortolozzi, Giuseppe Basso, and Giampietro Viola . Synthesis and Evaluation of 1,5-Disubstituted Tetrazoles as Rigid Analogues of Combretastatin A-4 with Potent Antiproliferative and Antitumor Activity. Journal of Medicinal Chemistry 2012, 55 (1) , 475-488. https://doi.org/10.1021/jm2013979
- George R. Pettit, Thomas H. Smith, Jun-Ping Xu, Delbert L. Herald, Erik J. Flahive, Collin R. Anderson, Paul E. Belcher, and John C. Knight . Antineoplastic Agents. 590. X-ray Crystal Structure of Dolastatin 16 and Syntheses of the Dolamethylleuine and Dolaphenvaline Units. Journal of Natural Products 2011, 74 (5) , 1003-1008. https://doi.org/10.1021/np100877h
- Fuchun Xie, Hongbing Zhao, Dewen Li, Hong Chen, Haitian Quan, Xiaojing Shi, Liguang Lou, and Youhong Hu . Synthesis and Biological Evaluation of 2,4,5-Substituted Pyrimidines as a New Class of Tubulin Polymerization Inhibitors. Journal of Medicinal Chemistry 2011, 54 (9) , 3200-3205. https://doi.org/10.1021/jm101388d
- Sébastien Combes, Pascale Barbier, Soazig Douillard, Anne McLeer-Florin, Véronique Bourgarel-Rey, Jean-Thomas Pierson, Alexey Yu. Fedorov, Jean-Pierre Finet, Jean Boutonnat, and Vincent Peyrot . Synthesis and Biological Evaluation of 4-Arylcoumarin Analogues of Combretastatins. Part 2. Journal of Medicinal Chemistry 2011, 54 (9) , 3153-3162. https://doi.org/10.1021/jm901826e
- Kyoko Nakagawa-Goto, Pei-Chi Wu, Chin-Yu Lai, Ernest Hamel, Hao Zhu, Liying Zhang, Takashi Kozaka, Emika Ohkoshi, Masuo Goto, Kenneth F. Bastow, and Kuo-Hsiung Lee . Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents. Journal of Medicinal Chemistry 2011, 54 (5) , 1244-1255. https://doi.org/10.1021/jm1011947
- Victor V. Semenov, Alex S. Kiselyov, Ilia Y. Titov, Irina K. Sagamanova, Natalie N. Ikizalp, Natalia B. Chernysheva, Dmitry V. Tsyganov, Leonid D. Konyushkin, Sergei I. Firgang, Roman V. Semenov, Irina B. Karmanova, Mikhail M. Raihstat, and Marina N. Semenova. Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes. Journal of Natural Products 2010, 73 (11) , 1796-1802. https://doi.org/10.1021/np1004278
- Wei Zhu, María Jiménez, Won-Hyuk Jung, Daniel P. Camarco, Raghavan Balachandran, Andreas Vogt, Billy W. Day and Dennis P. Curran. Streamlined Syntheses of (−)-Dictyostatin, 16-Desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-Desmethyl-25,26-dihydrodictyostatin. Journal of the American Chemical Society 2010, 132 (26) , 9175-9187. https://doi.org/10.1021/ja103537u
- George R. Pettit, Mathew D. Minardi, Fiona Hogan and Pat M. Price. An Efficient Synthetic Strategy for Obtaining 4-Methoxy Carbon Isotope Labeled Combretastatin A-4 Phosphate and Other Z-Combretastatins. Journal of Natural Products 2010, 73 (3) , 399-403. https://doi.org/10.1021/np9004486
- Samantha Gogola, Michael Rejzer, Robert Poppiti. Overcoming resistance in prostate cancer with targeted and small molecule-based therapies. 2024, 255-287. https://doi.org/10.1016/B978-0-443-16032-5.00008-7
- Mariangela Librizzi, Chiara Martino, Manuela Mauro, Giulia Abruscato, Vincenzo Arizza, Mirella Vazzana, Claudio Luparello. Natural Anticancer Peptides from Marine Animal Species: Evidence from In Vitro Cell Model Systems. Cancers 2024, 16 (1) , 36. https://doi.org/10.3390/cancers16010036
- Xueli Xu, Shanbin Xu, Jipeng Wan, Diqing Wang, Xinlong Pang, Yuan Gao, Nengyi Ni, Dawei Chen, Xiao Sun. Disturbing cytoskeleton by engineered nanomaterials for enhanced cancer therapeutics. Bioactive Materials 2023, 29 , 50-71. https://doi.org/10.1016/j.bioactmat.2023.06.016
- Sneha Venugopal, Balwinder Kaur, Anil Verma, Pankaj Wadhwa, Muskan Magan, Sharwan Hudda, Violina Kakoty. Recent advances of benzimidazole as anticancer agents. Chemical Biology & Drug Design 2023, 102 (2) , 357-376. https://doi.org/10.1111/cbdd.14236
- Qiao-Hong Chen. Crosstalk between Microtubule Stabilizing Agents and Prostate Cancer. Cancers 2023, 15 (13) , 3308. https://doi.org/10.3390/cancers15133308
- Brianna Hurysz, Blake A. Evans, Reuben N. Laryea, Brooke E. Boyer, Taylor E. Coburn, Molly S. Dexter, Marissa A. Edwards, Grace V. Faulkner, Rebecca L. Huss, Megan M. Lafferty, Maegan Manning, Matthew McNulty, Sophia J. Melvin, Christina M. Mitrow, Roslyn R. Patel, Kelsey Pierce, Jack Russo, Allie M. Seminer, Kaitlynn A. Sockett, Nathan R. Webster, Kathryn E. Cole, Patricia Mowery, Erin T. Pelkey. Synthesis, Modeling, and Biological Evaluation of Anti-Tubulin Indole-Substituted Furanones. Bioorganic & Medicinal Chemistry Letters 2023, 4 , 129347. https://doi.org/10.1016/j.bmcl.2023.129347
- Eleonora Turrini, Francesca Maffei, Carmela Fimognari. Effect of the Marine Polyketide Plocabulin on Tumor Progression. Marine Drugs 2023, 21 (1) , 38. https://doi.org/10.3390/md21010038
- Wei Yang, Huining Peng, Yong Huang, Zhiyun Peng, Guangcheng Wang. Synthesis and antitumor activity of litseaone B analogues as tubulin polymerisation inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 2022, 37 (1) , 2530-2539. https://doi.org/10.1080/14756366.2022.2122962
- Praveen Dhyani, Cristina Quispe, Eshita Sharma, Amit Bahukhandi, Priyanka Sati, Dharam Chand Attri, Agnieszka Szopa, Javad Sharifi-Rad, Anca Oana Docea, Ileana Mardare, Daniela Calina, William C. Cho. Anticancer potential of alkaloids: a key emphasis to colchicine, vinblastine, vincristine, vindesine, vinorelbine and vincamine. Cancer Cell International 2022, 22 (1) https://doi.org/10.1186/s12935-022-02624-9
- Godshelp O. Egharevba, Ahmed Kamal, Omotayo O. Dosumu, Sunitha Routhu, Olatomide A. Fadare, Stephen O. Oguntoye, Stanislaus N. Njinga, Abimbola P. Oluyori. Synthesis and characterization of novel combretastatin analogues of 1,1-diaryl vinyl sulfones, with antiproliferative potential via in-silico and in-vitro studies. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-05958-6
- Satya Kumar Avula, Biswanath Das, Rene Csuk, Ahmed Al-Harrasi. Naturally Occurring O-Heterocycles as Anticancer Agents. Anti-Cancer Agents in Medicinal Chemistry 2022, 22 (19) , 3208-3218. https://doi.org/10.2174/1871520621666211108091444
- Hualong Zhao, Siyuan Wang, Yilu Zhou, Ayse Ertay, Philip T. F. Williamson, Rob M. Ewing, Xinhui Tang, Jialian Wang, Yihua Wang. Integrated analysis reveals effects of bioactive ingredients from Limonium Sinense (Girard) Kuntze on hypoxia-inducible factor (HIF) activation. Frontiers in Plant Science 2022, 13 https://doi.org/10.3389/fpls.2022.994036
- Søren Brøgger Christensen. Drugs That Changed Society: Microtubule-Targeting Agents Belonging to Taxanoids, Macrolides and Non-Ribosomal Peptides. Molecules 2022, 27 (17) , 5648. https://doi.org/10.3390/molecules27175648
- Xuemin Zhao, Rui Zhang, Xiuyan Yu, Na Yu, Yuanze Shi, Mao Shu, Yan Shen. Discovery of novel tubulin polymerization inhibitors by utilizing 3D-QSAR, molecular docking and molecular dynamics simulation. New Journal of Chemistry 2022, 46 (34) , 16426-16435. https://doi.org/10.1039/D2NJ02773A
- Md Abdullah Al Noman, David S. Huang, Sara K. Coulup, Shameem Sultana Syeda, Henry, L. Wong, Gunda I. Georg. Cytotoxicity of phenylpironetin analogs and the metabolic fate of pironetin and phenylpironetin. Bioorganic Chemistry 2022, 125 , 105915. https://doi.org/10.1016/j.bioorg.2022.105915
- Adarsh Sahu. Combretastatin Derivatives as Microtubule Inhibitors of Colchicines Binding Site. Anti-Infective Agents 2022, 20 (3) https://doi.org/10.2174/2211352519666211119090754
- Khattab Al-Khafaji, Tugba Taskin-Tok. Computational techniques for studying protein-protein interactions. 2022, 125-135. https://doi.org/10.1016/B978-0-323-90264-9.00009-X
- Galal H. Elgemeie, Reham A. Mohamed-Ezzat. Natural products in chemotherapy of cancers. 2022, 507-546. https://doi.org/10.1016/B978-0-12-821783-2.00009-1
- Mohamed Ali Seyed, Siddiqua Ayesha. Marine-derived pipeline anticancer natural products: a review of their pharmacotherapeutic potential and molecular mechanisms. Future Journal of Pharmaceutical Sciences 2021, 7 (1) https://doi.org/10.1186/s43094-021-00350-z
- Shan Zhu, Wenhui Jiao, Yanglu Xu, Lanjiao Hou, Hui Li, Jingrong Shao, Xiaoliang Zhang, Ran Wang, Dexin Kong. Palmitic acid inhibits prostate cancer cell proliferation and metastasis by suppressing the PI3K/Akt pathway. Life Sciences 2021, 286 , 120046. https://doi.org/10.1016/j.lfs.2021.120046
- Chao Wang, Yujing Zhang, Yudong Wu, Dongming Xing. Developments of CRBN-based PROTACs as potential therapeutic agents. European Journal of Medicinal Chemistry 2021, 225 , 113749. https://doi.org/10.1016/j.ejmech.2021.113749
- Atul Kapoor, Jaspreet Kaur Rajput. Staudinger k etene–imine [2+2] cycloaddition of novel azomethines to synthesize biologically active azetidinone derivatives and their in vitro antimicrobial studies. Journal of Heterocyclic Chemistry 2021, 58 (12) , 2304-2323. https://doi.org/10.1002/jhet.4357
- Anja Beč, Lucija Hok, Leentje Persoons, Els Vanstreels, Dirk Daelemans, Robert Vianello, Marijana Hranjec. Synthesis, Computational Analysis, and Antiproliferative Activity of Novel Benzimidazole Acrylonitriles as Tubulin Polymerization Inhibitors: Part 2. Pharmaceuticals 2021, 14 (10) , 1052. https://doi.org/10.3390/ph14101052
- Yassine Laamari, Ali Oubella, Abdoullah Bimoussa, Az-Eddine El Mansouri, El Mostafa Ketatni, Olivier Mentre, My Youssef Ait Itto, Hamid Morjani, Mostafa Khouili, Aziz Auhmani. Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol. Bioorganic Chemistry 2021, 115 , 105165. https://doi.org/10.1016/j.bioorg.2021.105165
- Gang Gao, Yanbing Wang, Huiming Hua, Dahong Li, Chunlan Tang. Marine Antitumor Peptide Dolastatin 10: Biological Activity, Structural Modification and Synthetic Chemistry. Marine Drugs 2021, 19 (7) , 363. https://doi.org/10.3390/md19070363
- Abhilash Rana, Seema Bhatnagar. Advancements in folate receptor targeting for anti-cancer therapy: A small molecule-drug conjugate approach. Bioorganic Chemistry 2021, 112 , 104946. https://doi.org/10.1016/j.bioorg.2021.104946
- María Paz Saldías, Diego Maureira, Octavio Orellana-Serradell, Ian Silva, Boris Lavanderos, Pablo Cruz, Camila Torres, Mónica Cáceres, Oscar Cerda. TRP Channels Interactome as a Novel Therapeutic Target in Breast Cancer. Frontiers in Oncology 2021, 11 https://doi.org/10.3389/fonc.2021.621614
- Yu Chen, Yue Pan, Danrong Hu, Jinrong Peng, Ying Hao, Meng Pan, Liping Yuan, Yongyang Yu, Zhiyong Qian. Recent progress in nanoformulations of cabazitaxel. Biomedical Materials 2021, 16 (3) , 032002. https://doi.org/10.1088/1748-605X/abe396
- Buduma Komuraiah, Yichang Ren, Mingming Xue, Binbin Cheng, Jin Liu, Yao Liu, Jianjun Chen. Design, synthesis and biological evaluation of benz‐fused five‐membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities. Chemical Biology & Drug Design 2021, 97 (5) , 1109-1116. https://doi.org/10.1111/cbdd.13832
- Abdelfattah Faouzi, Alexandre Arnaud, Alexandre Bancet, Caroline Barette, Jordane Preto, Cong Viet Do, Lars Petter Jordheim, Zineb Bousfiha, Thi Thanh Binh Nguyen, Marion Verrière, Amaury Farce, Marie-Odile Fauvarque, Roland Barret, Thierry Lomberget. Combretastatin A-4 sulfur-containing heterocyclic derivatives: Synthesis, antiproliferative activities and molecular docking studies. European Journal of Medicinal Chemistry 2021, 215 , 113275. https://doi.org/10.1016/j.ejmech.2021.113275
- Filip Borys, Piotr Tobiasz, Marcin Poterała, Hanna Krawczyk. Development of novel derivatives of stilbene and macrocyclic compounds as potent of anti-microtubule factors. Biomedicine & Pharmacotherapy 2021, 133 , 110973. https://doi.org/10.1016/j.biopha.2020.110973
- Marika Mokou, Vasiliki Lygirou, Ioanna Angelioudaki, Nikolaos Paschalidis, Rafael Stroggilos, Maria Frantzi, Agnieszka Latosinska, Aristotelis Bamias, Michèle J. Hoffmann, Harald Mischak, Antonia Vlahou. A Novel Pipeline for Drug Repurposing for Bladder Cancer Based on Patients’ Omics Signatures. Cancers 2020, 12 (12) , 3519. https://doi.org/10.3390/cancers12123519
- Masaki Kita, Hideo Kigoshi. Discovery and Use of Natural Products and Derivatives as Chemical Probes. 2020, 124-149. https://doi.org/10.1039/9781839160745-00124
- Esmeralda J. Chávez-Estrada, Carlos M. Cerda-García-Rojas, Luisa U. Román-Marín, Juan D. Hernández-Hernández, Pedro Joseph-Nathan. Synthesis, molecular docking, and saturation-transfer difference NMR spectroscopy of longipinane derivatives as novel microtubule stabilizers. Journal of Molecular Structure 2020, 1218 , 128519. https://doi.org/10.1016/j.molstruc.2020.128519
- Meenakshi Singh, A. V. Amrutha Krishnan, Ramkrishna Mandal, Jayanta Samanta, V. Ravichandiran, Ramalingam Natarajan, Yogesh P. Bharitkar, Abhijit Hazra. Azomethine ylide cycloaddition: a versatile tool for preparing novel pyrrolizidino-spiro-oxindolo hybrids of the doubly conjugated alkamide piperine. Molecular Diversity 2020, 24 (3) , 627-639. https://doi.org/10.1007/s11030-019-09969-w
- Meenakshi Singh, V. Ravichandiran, Yogesh P. Bharitkar, Abhijit Hazra. Natural Products Containing Olefinic Bond: Important Substrates for Semi-synthetic Modification Towards Value Addition. Current Organic Chemistry 2020, 24 (7) , 709-745. https://doi.org/10.2174/1385272824666200312125734
- Ivana Gasic, Brian J. Groendyke, Radosław P. Nowak, J. Christine Yuan, Joann Kalabathula, Eric S. Fischer, Nathanael S. Gray, Timothy J. Mitchison. Tubulin Resists Degradation by Cereblon-Recruiting PROTACs. Cells 2020, 9 (5) , 1083. https://doi.org/10.3390/cells9051083
- M. Shaheer Malik, Saleh A. Ahmed, Ismail I. Althagafi, Mohammed Azam Ansari, Ahmed Kamal. Application of triazoles as bioisosteres and linkers in the development of microtubule targeting agents. RSC Medicinal Chemistry 2020, 11 (3) , 327-348. https://doi.org/10.1039/C9MD00458K
- Shabir Ahmad Ganai. Compendium of Mechanistic Insights of Distinct Conventional Anticancer Therapies and Their Grievous Toxicities. 2020, 111-136. https://doi.org/10.1007/978-981-15-8179-3_6
- Cassandra Yong, Shane M. Devine, Xuexin Gao, Angelina Yan, Richard Callaghan, Ben Capuano, Peter J. Scammells. A Novel Class of N ‐Sulfonyl and N ‐Sulfamoyl Noscapine Derivatives that Promote Mitotic Arrest in Cancer Cells. ChemMedChem 2019, 14 (23) , 1968-1981. https://doi.org/10.1002/cmdc.201900477
- Jian Yu, Yihan Zhang, Shuju Ning, Qi Ye, Hexin Tan, Ruibing Chen, Qitao Bu, Rui Zhang, Peimin Gong, Xiaoli Ma, Lei Zhang, Daozhi Wei. Molecular cloning and metabolomic characterization of the 5-enolpyruvylshikimate-3-phosphate synthase gene from Baphicacanthus cusia. BMC Plant Biology 2019, 19 (1) https://doi.org/10.1186/s12870-019-2035-0
- Koji Wada, Hiroshi Yamashita. Cytotoxic Effects of Diterpenoid Alkaloids Against Human Cancer Cells. Molecules 2019, 24 (12) , 2317. https://doi.org/10.3390/molecules24122317
- Florence Lefranc, Aikaterini Koutsaviti, Efstathia Ioannou, Alexander Kornienko, Vassilios Roussis, Robert Kiss, David Newman. Algae metabolites: from in vitro growth inhibitory effects to promising anticancer activity. Natural Product Reports 2019, 36 (5) , 810-841. https://doi.org/10.1039/C8NP00057C
- Hiroko Kamata, Sotaro Sadahiro, Takao Yamori. Discovery of Inhibitors of Membrane Traffic from a Panel of Clinically Effective Anticancer Drugs. Biological and Pharmaceutical Bulletin 2019, 42 (5) , 814-818. https://doi.org/10.1248/bpb.b18-01026
- Shengquan Hu, Wuji Sun, Yeming Wang, Hong Yan. Design, synthesis and anticancer activities of halogenated Phenstatin analogs as microtubule destabilizing agent. Medicinal Chemistry Research 2019, 28 (4) , 465-472. https://doi.org/10.1007/s00044-019-02299-4
- Asako Kaise, Yasuyuki Endo, Kiminori Ohta. Anti-cancer activity of m-carborane-containing trimethoxyphenyl derivatives through tubulin polymerization inhibition. Bioorganic & Medicinal Chemistry 2019, 27 (6) , 1139-1144. https://doi.org/10.1016/j.bmc.2019.02.018
- Mohamed H. Hekal, Fatma S. M. Abu El‐Azm, Hanan A. Sallam. Synthesis, Spectral Characterization, and In Vitro Biological Evaluation of Some Novel Isoquinolinone‐based Heterocycles as Potential Antitumor Agents. Journal of Heterocyclic Chemistry 2019, 56 (3) , 795-803. https://doi.org/10.1002/jhet.3448
- Valentina Laghezza Masci, Stefano Bernardini, Lorenzo Modesti, Elisa Ovidi, Antonio Tiezzi. Medicinal Plants as a Source of Alkaloids. 2019, 85-113. https://doi.org/10.1007/978-981-13-9566-6_5
- S. Ezrahi, A. Aserin, N. Garti. Basic principles of drug delivery systems – the case of paclitaxel. Advances in Colloid and Interface Science 2019, 263 , 95-130. https://doi.org/10.1016/j.cis.2018.11.004
- Majid M. Heravi, Vahideh Zadsirjan, Pegah Saedi, Tayebeh Momeni. Applications of Friedel–Crafts reactions in total synthesis of natural products. RSC Advances 2018, 8 (70) , 40061-40163. https://doi.org/10.1039/C8RA07325B
- Jyoti Chauhan, Moumita Dasgupta, Tania Luthra, Akanksha Awasthi, Sayantan Tripathy, Anindyajit Banerjee, Santanu Paul, Debasish Nag, Saikat Chakrabarti, Gopal Chakrabarti, Subhabrata Sen. Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO). European Journal of Pharmaceutical Sciences 2018, 124 , 249-265. https://doi.org/10.1016/j.ejps.2018.08.033
- Renata Mikstacka, Małgorzata Zielińska-Przyjemska, Zbigniew Dutkiewicz, Michał Cichocki, Tomasz Stefański, Mariusz Kaczmarek, Wanda Baer-Dubowska. Cytotoxic, tubulin-interfering and proapoptotic activities of 4′-methylthio-trans-stilbene derivatives, analogues of trans-resveratrol. Cytotechnology 2018, 70 (5) , 1349-1362. https://doi.org/10.1007/s10616-018-0227-3
- Mohamed H. Hekal, Fatma S. M. Abu El-Azm. New potential antitumor quinazolinones derived from dynamic 2-undecyl benzoxazinone: Synthesis and cytotoxic evaluation. Synthetic Communications 2018, 48 (18) , 2391-2402. https://doi.org/10.1080/00397911.2018.1490433
- David S. Huang, Henry L. Wong, Gunda I. Georg. Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. Bioorganic & Medicinal Chemistry Letters 2018, 28 (16) , 2789-2793. https://doi.org/10.1016/j.bmcl.2017.10.057
- Guangcheng Wang, Zhiyun Peng, Jiebing Zhang, Jie Qiu, Zhenzhen Xie, Zipeng Gong. Synthesis, biological evaluation and molecular docking studies of aminochalcone derivatives as potential anticancer agents by targeting tubulin colchicine binding site. Bioorganic Chemistry 2018, 78 , 332-340. https://doi.org/10.1016/j.bioorg.2018.03.028
- Hao Chen, Shuguo Li, Shuibin Wang, Weiping Li, Ning Bao, Wenbin Ai. The inhibitory effect of kokusaginine on the growth of human breast cancer cells and MDR-resistant cells is mediated by the inhibition of tubulin assembly. Bioorganic & Medicinal Chemistry Letters 2018, 28 (14) , 2490-2492. https://doi.org/10.1016/j.bmcl.2018.05.059
- Faria Sultana, Srinivasa Reddy Bonam, V. Ganga Reddy, V. Lakshma Nayak, Ravikumar Akunuri, Sunitha Rani Routhu, Abdullah Alarifi, M. Sampath Kumar Halmuthur, Ahmed Kamal. Synthesis of benzo[ d ]imidazo[2,1- b ]thiazole-chalcone conjugates as microtubule targeting and apoptosis inducing agents. Bioorganic Chemistry 2018, 76 , 1-12. https://doi.org/10.1016/j.bioorg.2017.10.019
- Guangcheng Wang, Jie Qiu, Xiangwei Xiao, Anbai Cao, Fengjiao Zhou. Synthesis, biological evaluation and molecular docking studies of a new series of chalcones containing naphthalene moiety as anticancer agents. Bioorganic Chemistry 2018, 76 , 249-257. https://doi.org/10.1016/j.bioorg.2017.11.017
- Quincy Quick. Microtubule-Actin Crosslinking Factor 1 and Plakins as Therapeutic Drug Targets. International Journal of Molecular Sciences 2018, 19 (2) , 368. https://doi.org/10.3390/ijms19020368
- Joshua M. Henkin, Yulin Ren, Djaja Djendoel Soejarto, A. Douglas Kinghorn. The Search for Anticancer Agents from Tropical Plants. 2018, 1-94. https://doi.org/10.1007/978-3-319-93506-5_1
- Danielle Twilley, Namrita Lall. The Role of Natural Products From Plants in the Development of Anticancer Agents. 2018, 139-178. https://doi.org/10.1016/B978-0-08-102081-4.00007-1
- Renzo Rossi, Marco Lessi, Chiara Manzini, Fabio Bellina. Synthesis and Biological Profiles of 4,5-, 1,5-, and 1,2-Diaryl-1 H -imidazoles. 2018, 83-160. https://doi.org/10.1016/B978-0-08-102237-5.00004-3
- S.J. Pyle, P.J. Meberg. Cytoskeletal Elements in Neurotoxicity. 2018, 101-119. https://doi.org/10.1016/B978-0-12-801238-3.65380-1
- Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier. galacto-C- Furanosides (I, β- C -Lyxose). 2018, 11-64. https://doi.org/10.1016/B978-0-12-803739-3.00002-2
- Tomasz Stefański, Renata Mikstacka, Rafał Kurczab, Zbigniew Dutkiewicz, Małgorzata Kucińska, Marek Murias, Małgorzata Zielińska-Przyjemska, Michał Cichocki, Anna Teubert, Mariusz Kaczmarek, Adam Hogendorf, Stanisław Sobiak. Design, synthesis, and biological evaluation of novel combretastatin A-4 thio derivatives as microtubule targeting agents. European Journal of Medicinal Chemistry 2018, 144 , 797-816. https://doi.org/10.1016/j.ejmech.2017.11.050
- Yang Ping Quan, Li Ping Cheng, Tian Chi Wang, Wan Pang, Fan Hong Wu, Jin Wen Huang. Molecular modeling study, synthesis and biological evaluation of combretastatin A-4 analogues as anticancer agents and tubulin inhibitors. MedChemComm 2018, 9 (2) , 316-327. https://doi.org/10.1039/C7MD00416H
- Kishore Mullagiri, V. Lakshma Nayak, Satish Sunkari, Geeta Sai Mani, Sravanthi Devi Guggilapu, Burri Nagaraju, Abdullah Alarifi, Ahmed Kamal. New (3-(1 H -benzo[ d ]imidazol-2-yl))/(3-(3 H -imidazo[4,5- b ]pyridin-2-yl))-(1 H -indol-5-yl)(3,4,5-trimethoxyphenyl)methanone conjugates as tubulin polymerization inhibitors. MedChemComm 2018, 9 (2) , 275-281. https://doi.org/10.1039/C7MD00450H
- Irene Briguglio, Erik Laurini, Maria Antonietta Pirisi, Sandra Piras, Paola Corona, Maurizio Fermeglia, Sabrina Pricl, Antonio Carta. Triazolopyridinyl-acrylonitrile derivatives as antimicrotubule agents: Synthesis, in vitro and in silico characterization of antiproliferative activity, inhibition of tubulin polymerization and binding thermodynamics. European Journal of Medicinal Chemistry 2017, 141 , 460-472. https://doi.org/10.1016/j.ejmech.2017.09.065
- Vijay K. Patel, Avineesh Singh, Deepak K. Jain, Preeti Patel, Ravichandran Veerasamy, Prabodh C. Sharma, Harish Rajak. Combretastatin A-4 based thiophene derivatives as antitumor agent: Development of structure activity correlation model using 3D-QSAR, pharmacophore and docking studies. Future Journal of Pharmaceutical Sciences 2017, 3 (2) , 71-78. https://doi.org/10.1016/j.fjps.2017.03.003
- Damian Plażuk, Anna Wieczorek, Wojciech M. Ciszewski, Karolina Kowalczyk, Andrzej Błauż, Sylwia Pawlędzio, Anna Makal, Chatchakorn Eurtivong, Homayon J. Arabshahi, Jóhannes Reynisson, Christian G. Hartinger, Błażej Rychlik. Synthesis and in vitro Biological Evaluation of Ferrocenyl Side‐Chain‐Functionalized Paclitaxel Derivatives. ChemMedChem 2017, 12 (22) , 1882-1892. https://doi.org/10.1002/cmdc.201700576
- Mohamed H. Hekal, Fatma S. M. Abu El‐Azm. Efficient MW‐Assisted Synthesis of Some New Isoquinolinone Derivatives With In Vitro Antitumor Activity. Journal of Heterocyclic Chemistry 2017, 54 (6) , 3056-3064. https://doi.org/10.1002/jhet.2916
- Florence Lefranc, Nurhayat Tabanca, Robert Kiss. Assessing the anticancer effects associated with food products and/or nutraceuticals using in vitro and in vivo preclinical development-related pharmacological tests. Seminars in Cancer Biology 2017, 46 , 14-32. https://doi.org/10.1016/j.semcancer.2017.06.004
- Santosh Kumar Choudhury, Pragati Rout, Bibhuti Bhusan Parida, Jean‐Claude Florent, Ludger Johannes, Ganngam Phaomei, Emmanuel Bertounesque, Laxmidhar Rout. Metal‐Free Activation of C(sp 3 )–H Bond, and a Practical and Rapid Synthesis of Privileged 1‐Substituted 1,2,3,4‐Tetrahydroisoquinolines. European Journal of Organic Chemistry 2017, 2017 (35) , 5275-5292. https://doi.org/10.1002/ejoc.201700471
- Thokhir B. Shaik, S.M. Ali Hussaini, V. Lakshma Nayak, M. Lakshmi Sucharitha, M. Shaheer Malik, Ahmed Kamal. Rational design and synthesis of 2-anilinopyridinyl-benzothiazole Schiff bases as antimitotic agents. Bioorganic & Medicinal Chemistry Letters 2017, 27 (11) , 2549-2558. https://doi.org/10.1016/j.bmcl.2017.03.089
- James I. Murray, Nils J. Flodén, Adriano Bauer, Nico D. Fessner, Daniel L. Dunklemann, Opetoritse Bob‐Egbe, Henry S. Rzepa, Thomas Bürgi, Jeffery Richardson, Alan C. Spivey. Kinetic Resolution of 2‐Substituted Indolines by N ‐Sulfonylation using an Atropisomeric 4‐DMAP‐ N ‐oxide Organocatalyst. Angewandte Chemie International Edition 2017, 56 (21) , 5760-5764. https://doi.org/10.1002/anie.201700977
- James I. Murray, Nils J. Flodén, Adriano Bauer, Nico D. Fessner, Daniel L. Dunklemann, Opetoritse Bob‐Egbe, Henry S. Rzepa, Thomas Bürgi, Jeffery Richardson, Alan C. Spivey. Kinetic Resolution of 2‐Substituted Indolines by N ‐Sulfonylation using an Atropisomeric 4‐DMAP‐ N ‐oxide Organocatalyst. Angewandte Chemie 2017, 129 (21) , 5854-5858. https://doi.org/10.1002/ange.201700977
- , , . 3: Alkaloids Potential Health Benefits and Toxicity. 2017, 60-85. https://doi.org/10.1201/9781315151540-4
- David S. Huang, Henry L. Wong, Gunda I. Georg. Synthesis and Cytotoxicity Evaluation of C4‐ and C5‐Modified Analogues of the α,β‐Unsaturated Lactone of Pironetin. ChemMedChem 2017, 12 (7) , 520-528. https://doi.org/10.1002/cmdc.201700084
- Hongshuang Li, Xiaming Wu, Ruize Zhang, Liqiang Hao, Guiyun Duan, Yuliang Xiao, Chengcai Xia, Furong Li, Guirong You, Junfen Han. Synthesis and biological evaluation of pyrano[2,3-f]chromene-4,8-dione derivatives as potential anticancer agents. Chemical Research in Chinese Universities 2017, 33 (2) , 187-193. https://doi.org/10.1007/s40242-017-6472-8
- Rati Lama, Chunfang Gan, Nethrie Idippily, Viharika Bobba, David Danielpour, Monica Montano, Bin Su. HMBA is a putative HSP70 activator stimulating HEXIM1 expression that is down-regulated by estrogen. The Journal of Steroid Biochemistry and Molecular Biology 2017, 168 , 91-101. https://doi.org/10.1016/j.jsbmb.2017.02.008