Cargando…

Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents

Chemical drug design based on the biochemical characteristics of cancer cells has become an important strategy for discovering new anti-tumour drugs to improve tumour targeting effects and reduce off-target toxicities. Colchicine is one of the most prominent and historically microtubule-targeting dr...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Chao, Zhang, Yujing, Wang, Zeyu, Li, Yuelin, Guan, Qi, Xing, Dongming, Zhang, Weige
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Taylor & Francis 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8725855/
https://www.ncbi.nlm.nih.gov/pubmed/34915785
http://dx.doi.org/10.1080/14756366.2021.2013832
_version_ 1784626199607115776
author Wang, Chao
Zhang, Yujing
Wang, Zeyu
Li, Yuelin
Guan, Qi
Xing, Dongming
Zhang, Weige
author_facet Wang, Chao
Zhang, Yujing
Wang, Zeyu
Li, Yuelin
Guan, Qi
Xing, Dongming
Zhang, Weige
author_sort Wang, Chao
collection PubMed
description Chemical drug design based on the biochemical characteristics of cancer cells has become an important strategy for discovering new anti-tumour drugs to improve tumour targeting effects and reduce off-target toxicities. Colchicine is one of the most prominent and historically microtubule-targeting drugs, but its clinical applications are hindered by notorious adverse effects. In this study, we presented a novel tumour-specific conjugate 9 that consists of deacetylcolchicine (Deac), biotin, and a cleavable disulphide linker. 9 was found to exhibit potent anti-tumour activity and exerted higher selectivity between tumour and nontarget cells than Deac. The targeting moiety biotin might enhance the transport capability and selectivity of 9 to tumour cells via biotin receptor-mediated endocytosis. The tubulin polymerisation activity of 9 (with DTT) was close to the parent drug Deac. These preliminary results suggested that 9 is a high potency and reduced toxicity antitumor agent and worthy of further investigation.
format Online
Article
Text
id pubmed-8725855
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Taylor & Francis
record_format MEDLINE/PubMed
spelling pubmed-87258552022-01-05 Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents Wang, Chao Zhang, Yujing Wang, Zeyu Li, Yuelin Guan, Qi Xing, Dongming Zhang, Weige J Enzyme Inhib Med Chem Research Paper Chemical drug design based on the biochemical characteristics of cancer cells has become an important strategy for discovering new anti-tumour drugs to improve tumour targeting effects and reduce off-target toxicities. Colchicine is one of the most prominent and historically microtubule-targeting drugs, but its clinical applications are hindered by notorious adverse effects. In this study, we presented a novel tumour-specific conjugate 9 that consists of deacetylcolchicine (Deac), biotin, and a cleavable disulphide linker. 9 was found to exhibit potent anti-tumour activity and exerted higher selectivity between tumour and nontarget cells than Deac. The targeting moiety biotin might enhance the transport capability and selectivity of 9 to tumour cells via biotin receptor-mediated endocytosis. The tubulin polymerisation activity of 9 (with DTT) was close to the parent drug Deac. These preliminary results suggested that 9 is a high potency and reduced toxicity antitumor agent and worthy of further investigation. Taylor & Francis 2021-12-16 /pmc/articles/PMC8725855/ /pubmed/34915785 http://dx.doi.org/10.1080/14756366.2021.2013832 Text en © 2021 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. https://creativecommons.org/licenses/by/4.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Paper
Wang, Chao
Zhang, Yujing
Wang, Zeyu
Li, Yuelin
Guan, Qi
Xing, Dongming
Zhang, Weige
Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title_full Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title_fullStr Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title_full_unstemmed Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title_short Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
title_sort design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents
topic Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8725855/
https://www.ncbi.nlm.nih.gov/pubmed/34915785
http://dx.doi.org/10.1080/14756366.2021.2013832
work_keys_str_mv AT wangchao designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT zhangyujing designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT wangzeyu designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT liyuelin designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT guanqi designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT xingdongming designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents
AT zhangweige designsynthesisandbiologicalevaluationofbiotinylatedcolchicinederivativesaspotentialantitumoragents