Citation: 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 shu

Antibacterial Fischer Carbenoid CO-Releasing Molecules

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

Corresponding author: Gao Ziwei, zwgao@snnu.edu.cn Zhang Weiqiang, zwq@snnu.edu.cn
Received Date: 16 March 2016
Revised Date: 9 May 2016

Fund Project: the Natural Science Basic Research Plan in Shaanxi Province 2012JM2006the Fundamental Doctoral Fund of Ministry of Education 20120202120005the National Natural Science Foundation of China 21371112the Fundamental Funds Research for the Central Universities GK201501005

Figures(9)

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.
- CO releasing molecules,
- Fischer carbene,
- quaternary ammonium salt,
- drug-resistant bacteria
1. [1]
  García-Gallego, S.; Bernardes, G. J. L. Angew. Chem., Int. Ed. 2014, 53, 9712. doi: 10.1002/anie.201311225
2. [2]
  Schatzschneider, U. Br. J. Pharmacol. 2015, 172, 1638. doi: 10.1111/bph.12688
3. [3]
  Tavares, A. F. N.; Nobre, L. S.; Saraiva, L. M. FEMS Microbiol. Lett. 2012, 336, 1. doi: 10.1111/fml.2012.336.issue-1
4. [4]
  Tavares, A. F. N.; Teixeira, M.; Romaõ, C. C.; Seixas, J. D.; Nobre, L. S.; Saraiva, L. M. J. Biol. Chem. 2011, 286, 26708. doi: 10.1074/jbc.M111.255752
5. [5]
  Books, J. C.; Alvarado, M.; Stephens, T. P.; Kellermeier, J. D.; Tittor, A. W.; Miller, M. F.; Brashears, M. M. J. Food Proteins 2008, 71, 93.
6. [6]
  Patra, M.; Gasser, G.; Wenzel, M.; Merz, K.; Bandow, J. E. Eur. J. Inorg. Chem. 2011, 3295.
7. [7]
  Foresti, R.; Bani-Hani, M. G.; Motterlini, R. Intensive Care Med. 2008, 34, 649. doi: 10.1007/s00134-008-1011-1
8. [8]
  Sandra, G. G.; Bernardes, G. J. L. Angew. Chem., Int. Ed. 2014, 53, 9712. doi: 10.1002/anie.201311225
9. [9]
  Romaõ, C. C.; Blättler, W. A.; Seixas, J. D.; Bernardes, G. J. L. Chem. Soc. Rev. 2012, 41, 3571. doi: 10.1039/c2cs15317c
10. [10]
  Wareham, L. K.; Poole1, R. K.; Mariana, T. T. J. Biol. Chem. 2015, 290, 18999. doi: 10.1074/jbc.R115.642926
11. [11]
  Clark, J. E.; Naughton, P.; Shurey, S.; Green, C. J.; Johnson, T. R.; Mann, B. E.; Foresti, R.; Motterlini, R. Circ. Res. 2003, 93, e2. doi: 10.1161/01.RES.0000084381.86567.08
12. [12]
  Nobre, L. S.; Seixas, J. D.; Romaõ, C. C.; Saraiva, L. M. Antimicrob. Agents Chemother. 2007, 4303.
13. [13]
  Desmard, M.; Foresti, R.; Boczkowski, J.; Motterlini, R.; Sawle, P. Antioxid. Redox Signaling 2012, 16, 153. doi: 10.1089/ars.2011.3959
14. [14]
  Zhang, W.-Q.; Atkin, A. J.; Thatcher, R. J.; Whitwood, A. C.; Fairlamb, I. J. S.; Lynam, J. M. Dalton Trans. 2009, 4351.
15. [15]
  Zhang, W.-Q..; Whitwood, A. C.; Fairlamb, I. J. S.; Lynam, J. M. Inorg. Chem. 2010, 49, 8941. doi: 10.1021/ic101230j
16. [16]
  Rimmer, R. D.; Richter, H.; Ford, P. C. Inorg. Chem. 2010, 49, 1180. doi: 10.1021/ic902147n
17. [17]
  Heldt, J. M.; Nathalie, F. D.; Salmain, M.; Vessières, A.; Jaouen, G. J. Organomet. Chem. 2004, 689, 4775. doi: 10.1016/j.jorganchem.2004.09.035
18. [18]
  Seixas, J. D.; Coelho, A. C.; Romão, C. C. Dalton Trans. 2015, 44, 5058. doi: 10.1039/C4DT02966F
19. [19]
  Crespy, D.; Landfester, K.; Schubert, U. S.; Schiller, A. Chem. Commun. 2010, 46, 6651. doi: 10.1039/c0cc01887b
20. [20]
  Furci, L. M.; Lopes, P.; Eakanunkul, S.; Zhong, S. J.; MacKerell, A. D.; Wilks, A. J. Med. Chem. 2007, 50, 3804. doi: 10.1021/jm0700969
21. [21]
  Edwards, E. I.; Epton, R.; Marr, G. J. Organomet. Chem. 1979, 168, 59.
22. [22]
  Edwards, E. I.; Epton, R.; Marr, G. J. Organomet. Chem. 1976, 122, C49. doi: 10.1016/S0022-328X(00)82406-7
23. [23]
  Edwards, E. I.; Epton, R.; Marr, G. J. Organomet. Chem. 1975, 85, C23.
24. [24]
  Andrews, J. M. J. Antimicrob. Chemother. 2001, 48, 5. doi: 10.1093/jac/48.suppl_1.5
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1.
沈阳化工大学材料科学与工程学院沈阳 110142