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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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 |
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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. |
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Article |
author |
Lin Y.-S. Tungpradit R. Sinchaikul S. An F.-M. Liu D.-Z. Phutrakul S. Chen S.-T. |
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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 |
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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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