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

IF 2.5 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemistryOpen Pub Date : 2024-10-14 DOI:10.1002/open.202400206

Simay Denizkusu, Ece Sabuncu, Hande Sipahi, Duygu Avci

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引用次数: 0

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 ¹H 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.

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具有更好溶解性和抗炎效果的新型布洛芬胱胺盐。

通过将布洛芬阴离子与胱胺二盐酸盐以 1 ：1 和 2 ：1 的比例将布洛芬阴离子与胱胺二盐酸盐偶联，以提高布洛芬的溶解度和生物利用度。这些盐通过 1H NMR、FT-IR 和 UV-Vis 光谱、差示扫描量热法（DSC）、热重法（TGA、DTA）和 X 射线衍射测量进行表征。与布洛芬（0.04 毫克/毫升）相比，IBU-CYS 1 和 IBU-CYS 2 在水中的溶解度更高（6.11 和 7.81 毫克/毫升）。IBU-CYS2 被封装在甲基丙烯酸 2-羟乙基酯：聚（乙二醇）丙烯酸酯水凝胶中，以增强给药效果。在 PBS（pH 值为 7.4）中进行的体外研究表明，这些盐类能有效缓解脂多糖在 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），同时表明它们没有细胞毒性。因此，这些盐类有可能成为开发该药物有效制剂的候选物质。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.80

自引率

4.30%

发文量

143

审稿时长

1 months

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