Improving Retinoic Acid Efficacy: Lipase-Catalyzed Synthesis of Derivatives with Antiviral Activity.

IF 2.6 4区 生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
ChemBioChem Pub Date : 2025-01-14 Epub Date: 2024-12-02 DOI:10.1002/cbic.202400728
Sofía C Bravo, Carlos A Montalbetti, Fabricio Freije García, Erina Petrera, Guadalupe García Liñares
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引用次数: 0

Abstract

An efficient enzymatic approach was applied to the synthesis of new derivatives of retinoic acid. Nine derivatives, four of them new compounds, were obtained through lipase-catalysis with excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile : substrate ratio, enzyme : substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. In addition, several synthesized compounds exhibited lower cytotoxicity than the retinoic acid in Vero cells and a remarkably higher antiviral activity against Herpes simplex virus type 1 (HSV-1) and Herpes simplex virus type 2 (HSV-2).

提高维甲酸疗效:脂肪酶催化合成具有抗病毒活性的衍生物。
一种高效的酶法被应用于合成维甲酸的新衍生物。通过脂肪酶催化获得了九种衍生物,其中四种是新化合物,且收率极高。为了找到最佳反应条件,研究了各种参数的影响,如酶源、亲核物与底物的比例、酶与底物的比例、溶剂和温度。考虑到反应条件温和、对环境影响小等优点,脂肪酶催化反应所获得的优异结果使该方法非常有效。此外,合成的几种化合物在 Vero 细胞中的细胞毒性低于维甲酸,而对 1 型单纯疱疹病毒(HSV-1)和 2 型单纯疱疹病毒(HSV-2)的抗病毒活性则明显高于维甲酸。
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来源期刊
ChemBioChem
ChemBioChem 生物-生化与分子生物学
CiteScore
6.10
自引率
3.10%
发文量
407
审稿时长
1 months
期刊介绍: ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).
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