Copper(II) complexes with different diamines as inhibitors of bacterial quorum sensing activity

Ivana M Stanojević; Ivana Aleksić; Nenad S Drašković; Biljana Dj Glišić; Sandra Vojnović; Jasmina Nikodinović-Runić

doi:10.2298/JSC170706087S

PDF (2,797 kB) Supplementary Material (2,13 MB)

Published: Dec 30, 2017

DOI: https://doi.org/10.2298/JSC170706087S

Keywords:

metal complexes nitrogen-donor ligands antimicrobial activity cytotoxicity interbacterial communication

Ivana M Stanojević

University of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac

Ivana Aleksić

Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade

Nenad S Drašković

University of Priština, Faculty of Agriculture, Kopaonička bb, 38228 Lešak

Biljana Dj Glišić

University of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac

Sandra Vojnović

Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade

Jasmina Nikodinović-Runić

Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade

Abstract

Three copper(II) complexes, trans-[Cu(1,3-pd)₂Cl₂]^.H₂O (Cu1; 1,3-pd is 1,3-propanediamine), trans-[Cu(2,2-diMe-1,3-pd)₂Cl₂] (Cu2; 2,2-diMe-1,3-pd is 2,2-dimethyl-1,3-propanediamine) and trans-[Cu(1,3-pnd)₂Cl₂]^.H₂O (Cu3; 1,3-pnd is (±)-1,3-pentanediamine), were synthesized and structurally characterized by elemental microanalyses, IR, electronic absorption and reflectance spectra and molar conductivity measurements. The antimicrobial efficiency of the complexes against four clinically relevant microorganisms and their antiproliferative effect on the normal human lung fibroblast cell line MRC-5 were evaluated. Since in many bacteria, pathogenicity is regulated by an intercellular communication process called quorum sensing (QS), the effect of the copper(II) complexes Cu1-3 on bacterial QS has been examined. The obtained results showed that these complexes inhibited violacein production in Chromobacterium violaceum CV026, indicating their anti-QS activity via homoserine lactone (HSL) pathway. Two biosensor strains were used to determine which pathway, C4-HSL (N-butanoyl-homoserine lactone) or 3OC12-HSL (N-3-oxododecanoyl-homoserine lactone), was affected by the copper(II) complexes. The biological activities of the copper(II) complexes were compared with those for the nickel(II) complexes of the general formula trans-[Ni(L)₂(H₂O)₂]Cl₂ (L = 1,3-pd, 2,2-diMe-1,3-pd and 1,3-pnd).

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

How to Cite

[1]

I. M. Stanojević, I. Aleksić, N. S. Drašković, B. D. Glišić, S. Vojnović, and J. Nikodinović-Runić, “Copper(II) complexes with different diamines as inhibitors of bacterial quorum sensing activity”, J. Serb. Chem. Soc., vol. 82, no. 12, pp. 1357–1367, Dec. 2017.

Issue

Vol. 82 No. 12 (2017)

Section

Inorganic Chemistry

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

References

K. D. Mjos, C. Orvig, Chem. Rev. 114 (2014) 4540

G. Gasser, N. Metzler-Nolte, Curr. Opin. Chem. Biol. 16 (2012) 84

M. Shabbir, Z. Akhter, J. Ahmad, S. Ahmed, V. McKee, H. Ismail, B. Mirza, Polyhedron 124 (2017) 117

C. Santini, M. Pellei, V. Gandin, M. Porchia, F. Tisato, C. Marzano, Chem. Rev. 114 (2014) 815

Z. L. Harris, J. D. Gitlin, Am. J. Clin. Nutr. 63 (1996) 836s

S. Labbe, D. J. Thiele, Trends Microbiol. 7 (1999) 500

L. Ruiz-Azuara, M. E. Bravo-Gomez, Curr. Med. Chem. 17 (2010) 3606

M. M. Harding, Acta Crystallogr., Sect. D: Biol. Crystallogr. 55 (1999) 1432

M. Diez, M. Arroyo, F. J. Cerdan, M. Munoz, M. A. Martin, J. L. Balibrea, Oncology 46 (1989) 230

K. Geraki, M. J. Farquharson, D. A. Bradley, Phys. Med. Biol. 47 (2002) 2327

D. Yoshida, Y. Ikeda, S. Nakazawa, J. Neurooncol. 16 (1993) 109

S. B. Nayak, V. R. Bhat, D. Upadhyay, S. L. Udupa, Indian J. Physiol. Pharmacol. 47 (2003) 108

M. E. Maragoudakis, Gen. Pharmacol. 35 (2000) 225

J. Folkman, Nat. Med. 1 (1995) 27

P. Szymański, T. Frączek, M. Markowicz, E. Mikiciuk-Olasik, Biometals 25 (2012) 1089

B. K. Singh, N. Bhojak, P. Mishra, B. S. Garg, Spectrochim. Acta, A 70 (2008) 758

A. P. Singh, N. K. Kaushik, A. K. Verma, G. Hundal, R. Gupta, Eur. J. Med. Chem. 44 (2009) 1607

M. N. Patel, P. A. Parmar, D. S. Gandhi, Bioorg. Med. Chem. 18 (2010) 1227

N. S. Ng, M. J. Wu, C. E. Jones, J. R. Aldrich-Wright, J. Inorg. Biochem. 162 (2016) 62

J. do Couto Almeida, I. M. Marzano, M. Pivatto, N. P. Lopes, A. M. Da Costa Ferreira, F. R. Pavan, I. C. Silva, E. C. Pereira-Maia, G. Von Poelhsitz, W. Guerra, Inorg. Chim. Acta 446 (2016) 87

B. Đ. Glišić, I. Aleksic, P. Comba, H. Wadepohl, T. Ilic-Tomic, J. Nikodinovic-Runic, M. I. Djuran, RSC Adv. 6 (2016) 86695

M. A. Welsh, N. R. Eibergen, J. D. Moore, H. E. Blackwell, J. Am. Chem. Soc. 137 (2015) 1510

S. Atkinson, P. Williams, J. R. Soc., Interface 6 (2009) 959

M. Juhas, L. Eberl, B. Tümmler, Environ. Microbiol. 7 (2005) 459

N. S. Drašković, B. Đ. Glišić, S. Vojnovic, J. Nikodinovic-Runic, M. I. Djuran, J. Serb. Chem. Soc. 82 (2017) 389

M. B. Hansen, S. E. Nielsen, K. Berg, J. Immunol. Methods 119 (1989) 203

K. H. McClean, M. K. Winson, L. Fish, A. Taylor, S. R. Chhabra, M. Camara, M. Daykin, J. H. Lamb, S. Swift, B. W. Bycroft, G. S. Stewart, P. Williams, Microbiology 143 (1997) 3703

F. Massai, F. Imperi, S. Quattrucci, E. Zennaro, P. Visca, L. Leoni, Biosens. Bioelectron. 26 (2011) 3444

K. Duan, M. G. Surette, J. Bacteriol. 189 (2007) 4827

K. S. Siddiqi, H. Afaq, S. A. A. Nami, A. Umar, Synth. React. Inorg. Met. – Org. Chem. 33 (2003) 1459

G. B. El-Hefnawy, M. El-Kersh, S. H. Etaiw, R. El-Tabbakh, Polyhedron 16 (1997) 3997

S. J. Obrey, S. G. Bott, A. R. Barron, J. Organomet. Chem. 643–644 (2002) 53

A. Wutkowski, C. Näther, W. Bensch, Inorg. Chim. Acta 379 (2011) 16

B. J. Hathaway, in Comprehensive Coordination Chemistry, Vol. 5, G. Wilkinson, R. D. Gillard, J. A. McCleverty, Eds., Pergamon, Oxford, 1987, p. 533

N. S. Drašković, D. D. Radanović, U. Rychlewska, B. Warżajtis, I. M. Stanojević, M. I. Djuran, Polyhedron 43 (2012)185

W. J. Geary, Coord. Chem. Rev. 7 (1971) 81

M. C. Sneed, J. L. Maynard, General Inorganic Chemistry, Van Nostrand, New York, 1942

G. G. Mohamed, Spectrochim. Acta, Part A 64 (2006) 188

S. Chattopadhyay, P. Chakraborty, M. G. B. Drew, A. Ghosh, Inorg. Chim. Acta 362 (2009) 502

K. Nakamoto, Infrared spectra of inorganic and coordination compounds, 2nd ed., Wiley, New York, 1970

M. Mousa AL-Noaimi, M. I. Choudhary, F. F. Awwadi, W. H. Talib, T. B. Hadda, S. Yousuf, A. Sawafta, I. Warad, Spectrochim. Acta, Part A 127 (2014) 225

Y.-H. Hu, W. Dang, C.-S. Liu, L. Sun, Lett. Appl. Microbiol. 50 (2010) 97

T. Nakayama, N. Nomura, M. Matsumura, J. Appl. Microbiol. 102 (2007) 1300.

Article Sidebar

Main Article Content

Abstract

Downloads

Metrics

Article Details

References

Most read articles by the same author(s)