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具有改善溶解性和抗炎作用的新型布洛芬胱胺盐

New Ibuprofen Cystamine Salts With Improved Solubility and Anti-Inflammatory Effect.

作者信息

Denizkusu Simay, Sabuncu Ece, Sipahi Hande, Avci Duygu

机构信息

Department of Chemistry, Bogazici University, 34342, Bebek, Istanbul, Turkey.

Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Yeditepe University, 34775, Istanbul, Turkey.

出版信息

ChemistryOpen. 2024 Dec;13(12):e202400206. doi: 10.1002/open.202400206. Epub 2024 Oct 14.

DOI:10.1002/open.202400206
PMID:39400468
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11625915/
Abstract

Two novel ibuprofen cystamine salts (IBU-CYS 1 and IBU-CYS 2) are synthesized by coupling the anion of ibuprofen with cystamine dihydrochloride in 1 : 1 and 2 : 1 ratio to improve the solubility and bioavailability of ibuprofen. The salts are characterized by H NMR, FT-IR and UV-Vis spectroscopy, differential scanning calorimetry (DSC), thermogravimetry (TGA, DTA) and X-ray diffraction measurements. IBU-CYS 1 and IBU-CYS 2 show higher solubility (6.11 and 7.81 mg/mL) compared to ibuprofen (0.04 mg/mL) in water. IBU-CYS2 was encapsulated into 2-hydroxyethyl methacrylate: poly (ethylene glycol) acrylate hydrogels for enhanced delivery. The in vitro studies in PBS (pH 7.4) indicate that the salts are effective in relieving inflammatory responses induced by lipopolysaccharide in RAW264.7 macrophage cells (nitrite inhibition percentages of IBU-CYS 1, IBU-CYS 2 and ibuprofen: approximately 34.29, 27.03 and 31.50 respectively) while indicating no cytotoxicity. Therefore, these salts may be promising candidates for the development of effective formulations of this drug.

摘要

通过将布洛芬阴离子与二盐酸半胱胺按1:1和2:1的比例偶联，合成了两种新型布洛芬半胱胺盐（IBU-CYS 1和IBU-CYS 2），以提高布洛芬的溶解度和生物利用度。通过核磁共振氢谱（H NMR）、傅里叶变换红外光谱（FT-IR）、紫外可见光谱（UV-Vis）、差示扫描量热法（DSC）、热重分析法（TGA、DTA）和X射线衍射测量对这些盐进行了表征。与布洛芬在水中的溶解度（0.04 mg/mL）相比，IBU-CYS 1和IBU-CYS 2的溶解度更高（分别为6.11和7.81 mg/mL）。将IBU-CYS2包裹于甲基丙烯酸2-羟乙酯：聚（乙二醇）丙烯酸酯水凝胶中以增强递送效果。在磷酸盐缓冲液（PBS，pH 7.4）中的体外研究表明，这些盐可有效减轻脂多糖在RAW264.7巨噬细胞中诱导的炎症反应（IBU-CYS 1、IBU-CYS 2和布洛芬的亚硝酸盐抑制率分别约为34.29、27.03和31.50），同时表明无细胞毒性。因此，这些盐可能是开发该药物有效制剂的有前景的候选物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/74ae662a30a0/OPEN-13-e202400206-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/ce883358acad/OPEN-13-e202400206-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/2a131d171ccc/OPEN-13-e202400206-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/ffa0d1253c46/OPEN-13-e202400206-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/74ae662a30a0/OPEN-13-e202400206-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/ce883358acad/OPEN-13-e202400206-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/2a131d171ccc/OPEN-13-e202400206-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/ffa0d1253c46/OPEN-13-e202400206-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd43/11625915/74ae662a30a0/OPEN-13-e202400206-g009.jpg

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