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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-10343342 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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