基于聚羟基链烷酸酯的3-羟基辛酸及其衍生物作为生物活性化合物的平台。,Applied Microbiology and Biotechnology

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基于聚羟基链烷酸酯的3-羟基辛酸及其衍生物作为生物活性化合物的平台。
Applied Microbiology and Biotechnology ( IF 3.9 ) Pub Date : 2015-09-25 , DOI: 10.1007/s00253-015-6984-4
Jelena Radivojevic _{1,

2} , Sanja Skaro ₂ , Lidija Senerovic ₁ , Branka Vasiljevic ₁ , Maciej Guzik _{3,

4} , Shane T Kenny ₃ , Veselin Maslak ₂ , Jasmina Nikodinovic-Runic ₂ , Kevin E O'Connor _{3,

5}

Affiliation

从（R）-3-羟基辛酸开始合成了18种不同化合物的库，该化合物衍生自细菌聚合物聚羟基链烷酸酯（PHA）。首次合成并表征了十个衍生物，包括卤代和不饱和甲基和苄基酯。考虑到已知（R）-3-羟基链烷酸具有生物活性，因此对这些新化合物的抗微生物活性和哺乳动物细胞系的体外抗增殖作用进行了评估。羧基的存在对于抗菌活性是必不可少的，对一组细菌（革兰氏阳性和革兰氏阴性）和真菌（白色念珠菌和石膏小孢子石膏）的抑制浓度最小，范围为2.8-7.0 mM和0.1-分别为6.3 mM。3-卤代辛酸具有抑制C的能力。白色念珠菌丝的形成。此外，（R）-3-羟基辛酸和（E）-辛-2-烯酸抑制机会病原体铜绿假单胞菌PAO1中的群体感应调节的洋青素生成。通常，即使在浓度为3-mM的情况下，衍生物也不会抑制哺乳动物细胞的增殖，而只有（E）-辛-2-烯酸和3-氧代辛酸在人肺成纤维细胞系中的IC50值为1.7和1.6 mM。

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Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds.

A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.

更新日期：2015-09-23

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