β-d-Ribofuranose as a Core with a Phosphodiester Moiety as the Enzyme Recognition Site for Codrug Development

Jih Ru Hwu; Avijit Panja; Shwu Chen Tsay; Wen Chieh Huang; Shu Yu Lin; Chen Sheng Yeh; Wu Chou Su; Li Xing Yang; Dar Bin Shieh

doi:10.1021/acs.orglett.4c03662

β-d-Ribofuranose as a Core with a Phosphodiester Moiety as the Enzyme Recognition Site for Codrug Development

Jih Ru Hwu, Avijit Panja, Shwu Chen Tsay, Wen Chieh Huang, Shu Yu Lin, Chen Sheng Yeh, Wu Chou Su, Li Xing Yang, Dar Bin Shieh

Research output: Contribution to journal › Article › peer-review

Abstract

An ideal codrug design should be able to control drug release, offer selectivity during drug delivery, and break down into non-toxic fragments after biodegradation. Our design incorporates d-ribofuranose as the core, with carbamate and carbonate groups as linking joints, a phosphodiester moiety as an enzyme recognition site, and lenalidomide and paclitaxel as the constituent drugs. The codrug synthesis involves seven steps with a 33% overall yield. The target codrug increases its water solubility 685 times versus paclitaxel.

Original language	English
Pages (from-to)	9865-9870
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.4c03662
Publication status	Published - 2024 Nov 22

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c03662

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abstract = "An ideal codrug design should be able to control drug release, offer selectivity during drug delivery, and break down into non-toxic fragments after biodegradation. Our design incorporates d-ribofuranose as the core, with carbamate and carbonate groups as linking joints, a phosphodiester moiety as an enzyme recognition site, and lenalidomide and paclitaxel as the constituent drugs. The codrug synthesis involves seven steps with a 33% overall yield. The target codrug increases its water solubility 685 times versus paclitaxel.",

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AU - Hwu, Jih Ru

AU - Panja, Avijit

AU - Tsay, Shwu Chen

AU - Huang, Wen Chieh

AU - Lin, Shu Yu

AU - Yeh, Chen Sheng

AU - Su, Wu Chou

AU - Yang, Li Xing

AU - Shieh, Dar Bin

PY - 2024/11/22

Y1 - 2024/11/22

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AB - An ideal codrug design should be able to control drug release, offer selectivity during drug delivery, and break down into non-toxic fragments after biodegradation. Our design incorporates d-ribofuranose as the core, with carbamate and carbonate groups as linking joints, a phosphodiester moiety as an enzyme recognition site, and lenalidomide and paclitaxel as the constituent drugs. The codrug synthesis involves seven steps with a 33% overall yield. The target codrug increases its water solubility 685 times versus paclitaxel.

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β-d-Ribofuranose as a Core with a Phosphodiester Moiety as the Enzyme Recognition Site for Codrug Development

Abstract

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