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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 11: 2695 - 2703

DOI: https://doi.org/10.6023/cjoc201603027

Articles

Antibacterial Fischer Carbenoid CO-Releasing Molecules

  • Zhou Lingling ,
  • Zhou Yaqing ,
  • Tang Yanli ,
  • Yang Kewu ,
  • Zhang Lei ,
  • Gao Lingxiang ,
  • Zhang Guofang ,
  • Gao Ziwei ,
  • Zhang Weiqiang
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  • 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 date: 2016-03-16

  Revised date: 2016-05-09

  Online 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).

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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]. Chinese Journal of Organic Chemistry, 2016 , 36(11) : 2695 -2703 . DOI: 10.6023/cjoc201603027

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