Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters

This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2′-paclitaxel and the 2′-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective...

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Main Authors: Lin Y.-S., Tungpradit R., Sinchaikul S., An F.-M., Liu D.-Z., Phutrakul S., Chen S.-T.
Format: Article
Language:English
Published: 2014
Online Access:http://www.scopus.com/inward/record.url?eid=2-s2.0-57349142938&partnerID=40&md5=af30ca40aab2c5becd270511b5bc1fb3
http://cmuir.cmu.ac.th/handle/6653943832/5343
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Institution: Chiang Mai University
Language: English
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spelling th-cmuir.6653943832-53432014-08-30T02:56:26Z Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters Lin Y.-S. Tungpradit R. Sinchaikul S. An F.-M. Liu D.-Z. Phutrakul S. Chen S.-T. This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2′-paclitaxel and the 2′-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective cytotoxicity against cancer cell lines, but showed reduced toxicity toward normal cell lines and cancer cell lines with low expression levels of GLUTs. The ester conjugated prodrug 1 showed the most cytotoxicity among the prodrugs examined and could be transported into cells via GLUTs. Fluorescent and confocal microscopy demonstrated that targeted cells exhibited morphological changes in tubulin and chromosomal alterations that were similar to those observed with paclitaxel treatment. Therefore, these glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs. © 2008 American Chemical Society. 2014-08-30T02:56:26Z 2014-08-30T02:56:26Z 2008 Article 00222623 10.1021/jm8006257 19053781 JMCMA http://www.scopus.com/inward/record.url?eid=2-s2.0-57349142938&partnerID=40&md5=af30ca40aab2c5becd270511b5bc1fb3 http://cmuir.cmu.ac.th/handle/6653943832/5343 English
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
language English
description This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2′-paclitaxel and the 2′-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective cytotoxicity against cancer cell lines, but showed reduced toxicity toward normal cell lines and cancer cell lines with low expression levels of GLUTs. The ester conjugated prodrug 1 showed the most cytotoxicity among the prodrugs examined and could be transported into cells via GLUTs. Fluorescent and confocal microscopy demonstrated that targeted cells exhibited morphological changes in tubulin and chromosomal alterations that were similar to those observed with paclitaxel treatment. Therefore, these glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs. © 2008 American Chemical Society.
format Article
author Lin Y.-S.
Tungpradit R.
Sinchaikul S.
An F.-M.
Liu D.-Z.
Phutrakul S.
Chen S.-T.
spellingShingle Lin Y.-S.
Tungpradit R.
Sinchaikul S.
An F.-M.
Liu D.-Z.
Phutrakul S.
Chen S.-T.
Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
author_facet Lin Y.-S.
Tungpradit R.
Sinchaikul S.
An F.-M.
Liu D.-Z.
Phutrakul S.
Chen S.-T.
author_sort Lin Y.-S.
title Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
title_short Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
title_full Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
title_fullStr Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
title_full_unstemmed Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
title_sort targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters
publishDate 2014
url http://www.scopus.com/inward/record.url?eid=2-s2.0-57349142938&partnerID=40&md5=af30ca40aab2c5becd270511b5bc1fb3
http://cmuir.cmu.ac.th/handle/6653943832/5343
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