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A General Protocol for Synthesizing Thiolated Folate Derivatives

Folic acid (FA) has shown great potential in the fields of targeted drug delivery and disease diagnosis due to its highly tumor-targeting nature, biocompatibility, and low cost. However, FA is generally introduced in targeted drug delivery systems through macromolecular linkage via complex synthetic...

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Autores principales: Li, Jie, Wang, Yao, Shan, Liangang, Qian, Lei, Wang, Wenchao, Liu, Jixian, Tang, Jianguo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343342/
https://www.ncbi.nlm.nih.gov/pubmed/37446887
http://dx.doi.org/10.3390/molecules28135228
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author Li, Jie
Wang, Yao
Shan, Liangang
Qian, Lei
Wang, Wenchao
Liu, Jixian
Tang, Jianguo
author_facet Li, Jie
Wang, Yao
Shan, Liangang
Qian, Lei
Wang, Wenchao
Liu, Jixian
Tang, Jianguo
author_sort Li, Jie
collection PubMed
description Folic acid (FA) has shown great potential in the fields of targeted drug delivery and disease diagnosis due to its highly tumor-targeting nature, biocompatibility, and low cost. However, FA is generally introduced in targeted drug delivery systems through macromolecular linkage via complex synthetic processes, resulting in lower yields and high costs. In this work, we report a general protocol for synthesizing thiolated folate derivatives. The small molecule thiolated folate (TFa) was first synthesized with a purity higher than 98.20%. First, S-S-containing diol was synthesized with a purity higher than 99.44 through a newly developed green oxidation protocol, which was carried out in water with no catalyst. Then, folic acid was modified using the diol through esterification, and TFa was finally synthesized by breaking the disulfide bond. Further, the synthesized TFa was utilized to modify silver nanoparticles. The results showed that TFa could be easily bonded to metal particles. The protocol could be extended to the synthesis of a series of thiolated derivatives of folate, such as mercaptohexyl folate, mercaptoundecyl folate, etc., which would greatly benefit the biological applications of FA.
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spelling pubmed-103433422023-07-14 A General Protocol for Synthesizing Thiolated Folate Derivatives Li, Jie Wang, Yao Shan, Liangang Qian, Lei Wang, Wenchao Liu, Jixian Tang, Jianguo Molecules Communication Folic acid (FA) has shown great potential in the fields of targeted drug delivery and disease diagnosis due to its highly tumor-targeting nature, biocompatibility, and low cost. However, FA is generally introduced in targeted drug delivery systems through macromolecular linkage via complex synthetic processes, resulting in lower yields and high costs. In this work, we report a general protocol for synthesizing thiolated folate derivatives. The small molecule thiolated folate (TFa) was first synthesized with a purity higher than 98.20%. First, S-S-containing diol was synthesized with a purity higher than 99.44 through a newly developed green oxidation protocol, which was carried out in water with no catalyst. Then, folic acid was modified using the diol through esterification, and TFa was finally synthesized by breaking the disulfide bond. Further, the synthesized TFa was utilized to modify silver nanoparticles. The results showed that TFa could be easily bonded to metal particles. The protocol could be extended to the synthesis of a series of thiolated derivatives of folate, such as mercaptohexyl folate, mercaptoundecyl folate, etc., which would greatly benefit the biological applications of FA. MDPI 2023-07-05 /pmc/articles/PMC10343342/ /pubmed/37446887 http://dx.doi.org/10.3390/molecules28135228 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Li, Jie
Wang, Yao
Shan, Liangang
Qian, Lei
Wang, Wenchao
Liu, Jixian
Tang, Jianguo
A General Protocol for Synthesizing Thiolated Folate Derivatives
title A General Protocol for Synthesizing Thiolated Folate Derivatives
title_full A General Protocol for Synthesizing Thiolated Folate Derivatives
title_fullStr A General Protocol for Synthesizing Thiolated Folate Derivatives
title_full_unstemmed A General Protocol for Synthesizing Thiolated Folate Derivatives
title_short A General Protocol for Synthesizing Thiolated Folate Derivatives
title_sort general protocol for synthesizing thiolated folate derivatives
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343342/
https://www.ncbi.nlm.nih.gov/pubmed/37446887
http://dx.doi.org/10.3390/molecules28135228
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