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白藜芦醇和虎杖苷与 L-脯氨酸共晶：晶体结构、溶解性能和体外细胞毒性。

Co-Crystals of Resveratrol and Polydatin with L-Proline: Crystal Structures, Dissolution Properties, and In Vitro Cytotoxicities.

机构信息

First Clinical Medical College, Zhejiang Chinese Medical University, Hangzhou 310053, China.

Department of Chemistry, Zhejiang University, Hangzhou 310028, China.

出版信息

Molecules. 2021 Sep 21;26(18):5722. doi: 10.3390/molecules26185722.

DOI:10.3390/molecules26185722
PMID:34577193
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8469398/
Abstract

Resveratrol (RSV) and polydatin (PD) have been widely used to treat several chronic diseases, such as atherosclerosis, pulmonary fibrosis, and diabetes, among several others. However, their low solubility hinders their further applications. In this work, we show that the solubility of PD can be boosted via its co-crystallization with L-proline (L-Pro). Two different phases of co-crystals, namely the RSV-L-Pro (RSV:L-Pro = 1:2) and PD-L-Pro (PD:L-Pro = 1: 3), have been prepared and characterized. As compared to the pristine RSV and PD, the solubility and dissolution rates of PD-L-Pro in water (pH 7.0) exhibited a 15.8% increase, whereas those of RSV-L-Pro exhibited a 13.8% decrease. A 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay of pristine RSV, PD, RSV-L-Pro, and PD-L-Pro against lung cancer cell line A549 and human embryonic kidney cell line HEK-293 indicated that both compounds showed obvious cytotoxicity against A549, but significantly reduced cytotoxicity against HEK-293, with PD/PD-L-Pro further exhibiting better biological safety than that of RSV/RSV-L-Pro. This work demonstrated that the readily available and biocompatible L-Pro can be a promising adjuvant to optimize the physical and chemical properties of RSV and PD to improve their pharmacokinetics.

摘要

白藜芦醇（RSV）和虎杖苷（PD）已被广泛用于治疗多种慢性疾病，如动脉粥样硬化、肺纤维化和糖尿病等。然而，它们的低溶解度限制了它们的进一步应用。在这项工作中，我们表明 PD 的溶解度可以通过与 L-脯氨酸（L-Pro）共结晶来提高。已经制备和表征了两种不同相的共晶体，即 RSV-L-Pro（RSV:L-Pro = 1:2）和 PD-L-Pro（PD:L-Pro = 1:3）。与原始 RSV 和 PD 相比，PD-L-Pro 在水中（pH 7.0）的溶解度和溶解速率提高了 15.8%，而 RSV-L-Pro 的溶解度和溶解速率则降低了 13.8%。3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四氮唑溴盐（MTT）测定原始 RSV、PD、RSV-L-Pro 和 PD-L-Pro 对肺癌细胞系 A549 和人胚肾细胞系 HEK-293 的活性表明，这两种化合物对 A549 均表现出明显的细胞毒性，但对 HEK-293 的细胞毒性明显降低，且 PD/PD-L-Pro 的生物安全性优于 RSV/RSV-L-Pro。这项工作表明，易于获得且生物相容的 L-Pro 可以作为一种有前途的佐剂，以优化 RSV 和 PD 的物理化学性质，改善它们的药代动力学。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/a080b834d291/molecules-26-05722-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8f0ded478d95/molecules-26-05722-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/ccc747216073/molecules-26-05722-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/ebf5728ef105/molecules-26-05722-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8c6b73db782c/molecules-26-05722-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/542680ee0ab8/molecules-26-05722-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/4775efe5f570/molecules-26-05722-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8ba6b7050eb0/molecules-26-05722-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/d78b5c4fdae9/molecules-26-05722-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/25c7b965dcec/molecules-26-05722-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/a080b834d291/molecules-26-05722-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8f0ded478d95/molecules-26-05722-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/ccc747216073/molecules-26-05722-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/ebf5728ef105/molecules-26-05722-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8c6b73db782c/molecules-26-05722-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/542680ee0ab8/molecules-26-05722-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/4775efe5f570/molecules-26-05722-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/8ba6b7050eb0/molecules-26-05722-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/d78b5c4fdae9/molecules-26-05722-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/25c7b965dcec/molecules-26-05722-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cb7/8469398/a080b834d291/molecules-26-05722-g010.jpg

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