Antibacterial Fischer Carbenoid CO-Releasing Molecules

doi:10.6023/cjoc201603027

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (11): 2695-2703.DOI: 10.6023/cjoc201603027 Previous Articles Next Articles

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抑菌型Fischer卡宾类一氧化碳缓释分子

周玲玲^a, 周亚青^a, 唐艳丽^a, 杨科武^b, 张雷^c, 高玲香^a, 张国防^a, 高子伟^a, 张伟强^a

a 陕西师范大学化学化工学院西安 710062;
b 西北大学材料与化学科学学院西安 710069;
c 解放军第二医科大学上海长征医院上海 200000

收稿日期:2016-03-16 修回日期:2016-05-09 发布日期:2016-07-07
通讯作者: 高子伟, 张伟强 E-mail:zwgao@snnu.edu.cn;zwq@snnu.edu.cn
基金资助:
国家自然科学基金（No.21371112）、教育部博士点新教师基金（No.20120202120005）、中央高校基金（No.GK201501005）和陕西省自然科学基金（No.2012JM2006）资助项目.

Antibacterial Fischer Carbenoid CO-Releasing Molecules

Zhou Lingling^a, Zhou Yaqing^a, Tang Yanli^a, Yang Kewu^b, Zhang Lei^c, Gao Lingxiang^a, Zhang Guofang^a, Gao Ziwei^a, Zhang Weiqiang^a

a Key Laboratory of Applied Surface and Colloid Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062;
b College of Chemistry & Materials Science, Northwest University, Xi'an 710069;
c Shang Hai Chang Zheng Hospital, The People's Liberation Army Second Medical University, Shanghai 200000

Received:2016-03-16 Revised:2016-05-09 Published:2016-07-07
Supported by:
Project supported by the National Natural Science Foundation of China (No.21371112),the Fundamental Doctoral Fund of Ministry of Education (No.20120202120005),the Fundamental Funds Research for the Central Universities (No.GK201501005) and the Natural Science Basic Research Plan in Shaanxi Province (No.2012JM2006).

1. Antibacterial Fischer Carbenoid CO-Releasing Molecules.PDF(6070KB)

Abstract

CO releasing molecules (CORMs) of transition metal carbonyl complexes are emerging as a new interdisciplinary advance of inorganic chemistry, biological medicine and materials chemistry. In this paper, new ionic Fischer carbene carbonyl complexes were devised, in which Cr, Mo and W metals as metallic center carried five CO whilst the quaternary ammonium finely tuned the water solubility of Fc-CORMs. The myoglobin assays showed that one Fc-CORM released at least two molecules of carbon monoxide in well-controlled fashion under physiological conditions. The structure-releasing correlation revealed that the central metal was the key factor governing their carbon monoxide release behavior. The CO release rate of Fc-CORM-Mo (2a~2e) is quicker than Fc-CORM-Cr (1a~1e), much faster than Fc-CORM-W (3a~3e). The antibacterial activity test found that Fc-CORM (1b) with medium CO release rate effectively inhibited the growth and survival of Escherichia coli, with an minimal inhibitory concentration (MIC) value of 30 μmol/L. As for drug-resistant bacteria, Fc-CORM (2a~2e) and Fc-CORM (3a~3e) showed bactericidal activity. Mechanism study indicated that the antibacterial activity relied on the CO release rate of Fc-CORMs.

Key words: CO releasing molecules, Fischer carbene, quaternary ammonium salt, drug-resistant bacteria

Cite this article

Zhou Lingling, Zhou Yaqing, Tang Yanli, Yang Kewu, Zhang Lei, Gao Lingxiang, Zhang Guofang, Gao Ziwei, Zhang Weiqiang. Antibacterial Fischer Carbenoid CO-Releasing Molecules[J]. Chin. J. Org. Chem., 2016, 36(11): 2695-2703.

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抑菌型Fischer卡宾类一氧化碳缓释分子

Antibacterial Fischer Carbenoid CO-Releasing Molecules

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