title: Design, synthesis, and antimicrobial activities of new tanshinone IIA esters.
abstract: Sixteen new ester derivatives with various partition coefficient (ClogP) values of tanshinone IIA (TSIIA), a major lipophilic component of Salvia miltiorrhiza, were designed and synthesised, including six aliphatic esters (3a-e, 5a), one phosphate ester (4c) and nine aromatic esters (5b-j). Their antimicrobial activities against three Gram-positive bacteria strains, Staphylococcus aureus, Bacillus subtilis, and Bacillus amyloliquefaciens, and two Gram-negative bacteria strains, Pseudomonas aeruginosa and Escherichia coli, as well as two fungi species, Candida albicans and Saccharomyces cerevisiae, were evaluated in vitro by broth microdilution susceptibility tests. The results showed that keeping ClogP values in a certain range is necessary for their antimicrobial activities. For those compounds with ClogP values between 5 and 10, their MIC values showed positive correlations with ClogP values. In particular, compound 3e exhibited fourfold and twofold higher potency than the standard drug amphotericin B against fungi C. albicans and S. cerevisiae with MIC values of 1.95 and 7.81 μg/mL, respectively.
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: Lin-Wei
authors.initials: LW
authors.lastname: Zeng
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: Chang-Xin
authors.initials: CX
authors.lastname: Zhou
authors.affiliation: b State Key Lab of Pharmaceutical Biotechnology, School of Life Sciences , Nanjing University , Nanjing , P.R. China.
authors.forename: Jia-Dong
authors.initials: JD
authors.lastname: Liu
authors.affiliation: b State Key Lab of Pharmaceutical Biotechnology, School of Life Sciences , Nanjing University , Nanjing , P.R. China.
authors.forename: Chang-Hong
authors.initials: CH
authors.lastname: Liu
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: Jian-Xia
authors.initials: JX
authors.lastname: Mo
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: A-Fang
authors.initials: AF
authors.lastname: Hou
authors.affiliation: c Zhejiang Chemical Industry Research Institute Co. Ltd , Hangzhou , P.R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Yao
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: Zhen-Zhen
authors.initials: ZZ
authors.lastname: Wang
authors.affiliation: a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
authors.forename: Li-She
authors.initials: LS
authors.lastname: Gan
keywords: ClogP; Tanshinone IIA; antimicrobial; ester derivatives; synthesis