Cefoperazone metal complexes and their antimicrobial investigations

Mehmet Emin Çınar; Taner Erdoğan; Ayşegül Gölcü

doi:10.18596/jotcsa.721414

Research Article

Cefoperazone metal complexes and their antimicrobial investigations

Year 2021, Volume: 8 Issue: 2, 375 - 390, 31.05.2021

Mehmet Emin Çınar Taner Erdoğan Ayşegül Gölcü

https://doi.org/10.18596/jotcsa.721414

Cited By: 1

Abstract

Transition metal (Cd(II), Co(II), Cu(II), Fe(III), Ni(II), Pd(II), Pt(II), Ru(III), Zn(II)) complexes of cefoperazone (CFP) were synthesized and their spectroscopic (IR, UV-Vis), magnetic, thermal (DTA-TG) and mass investigations were conducted to characterize the metal-based complexes. Detailed insights into the electronic structures were provided by performing density functional theory (DFT) computations. Their antimicrobial studies were realized rendering their activities compared to that of the commercial cefoperazone.

Keywords

Cefoperazone, metal complexes, antimicrobial studies, computation

Supporting Institution

TUBITAK

Project Number

105T371

Thanks

The authors wish to thank TUBITAK (Project No: 105T371) for the financial support; Kahramanmaras Sutcu Imam University, Chemistry Department for laboratory environments; and Kahramanmaras Sutcu Imam University, Biology Department for cell culture studies. We thank the Istanbul Technical University for the laboratory (L105) facilities to redo the experiments. We are indebted to the Kocaeli University for the computer time provided.

References

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7. Ceylan BI.Oxovanadium(IV)-containing N2O2 chelate complex; crystal structure determination and DFT. Journal of the Turkish Chemical Society, Section A: Chemistry. 2016;3:393-402.
8. Akdemir N. Synthesis, characterization, and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, computational and experimental studies of 4-(2,3,5-trimethylphenoxy)phthalonitrile. Journal of the Turkish Chemical Society, Section A: Chemistry. 2016;3:683-706.
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12. Lu T, Chen F. Multiwfn: A multifunctional wavefunction analyzer. J. Comput. Chem. 2012;33:580-92.
13. O'Boyle NM, Tenderholt AL, Langner KM. cclib: A library for package–independent computational chemistry algorithms. J. Comp. Chem. 2008;29:839-45.
14. Cancès E, Mennucci B, Tomasi J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 1997;107:3032-41.
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16. Mennucci B, Cancès E, Tomasi J. Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications. J. Phys. Chem. B. 1997;101:10506-17.
17. Anacona J, Silva GD. Synthesis and antibacterial activity of cefotaxime metal complexes. J. Chil. Chem. Soc. 2005;50:447-50.
18. Fuliaş A, Bobric A, Vlase G, Vlase T, Doca N. Thermal stability and biological interactions. of some cephalosporins. Rev. Roum. Chim. 2011;56:959-66.
19. Barnes DJ, Chapman RL, Stephens FS, Vagg RS. Studies on the metal-amide bond. VII. Metal complexes of the flexible N4 ligand N,N′-bis(2′- pyridinecarboxamide)1,2-ethane. Inorg. Chim. Acta. 1981;51:155-62.
20. Garg BS, Bhojak N, Dwivedi P, Kumar V. Copper(II) complexes of acid amide derivatives of 2-aminopyridineand an exogenous ligand. Transit. Metal. Chem. 1999;24: 463-6.
21. Anacona JR, Bravo A, Lopez ME, Antibacterial Activity of Cefoperazone Metal Complexes. Lat. Am. J. Pharm. 2012;31:27-31.
22. Franchini GC, Giusti A, Preti C, Tosi L, Zannini P. Coordinating ability of methylpiperidine dithiocarbamates towards platinum group metals. Polyhedron, 1985, 9, 1553-1558.
23. Castillo M, Criado JJ, Macias B, Vaquero MV. Chemistry of dithiocarbamate derivatives of amino acids. I. Study of some dithiocarbamate derivatives of linear α-amino acids and their nickel(II) complexes. Inorg. Chim. Acta. 1986;124:127-32.
24. El-Aziz AOA, El-Dars FM, Radowan AA. Novel all-solid contact Copper (II) - selective sensor based on Cefoperazone and poly(3,4-ethylenedioxythiophene) (PEDOT) as conducting polymer. Journal of Inventions in Biomedical and Pharmaceutical Sciences (JIBPS). 2016;1:24-31.
25. Shungu, DL, Tutlane V, Gadebusch HH. Multicenter evaluation of the proposed quality control limits and interpretive zone standards for in vitro susceptibility testing with norfloxacin. J. Clin. Microbiol. 1983;18:988-91.
26. Shungu DL, Weinberg E, Gadebusch, HH. Tentative interpretive standards for disk diffusion susceptibility testing with norfloxacin (MK-0366, AM-715). Antimicrob. Agents Chemother. 1983;23:256-60.

Year 2021, Volume: 8 Issue: 2, 375 - 390, 31.05.2021

Mehmet Emin Çınar Taner Erdoğan Ayşegül Gölcü

https://doi.org/10.18596/jotcsa.721414

Cited By: 1

Abstract

Project Number

105T371

References

1. Badr IHA, Saleh GA, Sayed SM, Nour El-Deen DAM. A Novel Membrane Sensor for Batch and Flow Injection Potentiometric Determination of Cefazolin Sodium in Pharmaceutical Preparations. Int. J. Electrochem. Sci. 2014;9:1621-36.
2. Percin-Ozkorucuklu S, Uka B, Yildirim-Bastemur G. Voltammetric analysis of cephalexin and cefazolin in pharmaceutical formulations and biological samples. Journal of the Turkish Chemical Society, Section A: Chemistry. 2019;6:217-24.
3. Masoud MS, Ali AE, Elasala GS, Kolkaila SA. Spectroscopic Studies and Thermal Analysis on Cefoperazone Metal Complexes. J. Chem. Pharm. Res. 2017;9:171-9.
4. Alekseev VG. Metal complexes of penicillins and cephalosporins. Pharm. Chem. J. 2012;45:679-97.
5. Anacona JR, Bravo A, Lopez ME. Cefoperazone metal complexes: synthesis and characterization. J. Chil. Chem. Soc. 2013;58:1520-3.
6. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 09, Rev.D.01, Gaussian, Inc., Wallingford CT, 2013.
7. Ceylan BI.Oxovanadium(IV)-containing N2O2 chelate complex; crystal structure determination and DFT. Journal of the Turkish Chemical Society, Section A: Chemistry. 2016;3:393-402.
8. Akdemir N. Synthesis, characterization, and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, computational and experimental studies of 4-(2,3,5-trimethylphenoxy)phthalonitrile. Journal of the Turkish Chemical Society, Section A: Chemistry. 2016;3:683-706.
9. Irikura KK, Johnson RD, Kacker RN. Uncertainties in scaling factors for ab initio vibrational frequencies. J. Phys. Chem. A. 2005;109:8430-37.
10. Dennington R, Keith T, Millam J. GaussView, Version 5. 2009, Semichem Inc.: Shawnee Mission, KS.
11. Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GRJ. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. Cheminformatics. 2012;4:1-17.
12. Lu T, Chen F. Multiwfn: A multifunctional wavefunction analyzer. J. Comput. Chem. 2012;33:580-92.
13. O'Boyle NM, Tenderholt AL, Langner KM. cclib: A library for package–independent computational chemistry algorithms. J. Comp. Chem. 2008;29:839-45.
14. Cancès E, Mennucci B, Tomasi J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 1997;107:3032-41.
15. Cancès E, Mennucci B. New applications of integral equations methods for solvation continuum models: ionic solutions and liquid crystals. J. Math. Chem. 1998;23:309-26.
16. Mennucci B, Cancès E, Tomasi J. Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications. J. Phys. Chem. B. 1997;101:10506-17.
17. Anacona J, Silva GD. Synthesis and antibacterial activity of cefotaxime metal complexes. J. Chil. Chem. Soc. 2005;50:447-50.
18. Fuliaş A, Bobric A, Vlase G, Vlase T, Doca N. Thermal stability and biological interactions. of some cephalosporins. Rev. Roum. Chim. 2011;56:959-66.
19. Barnes DJ, Chapman RL, Stephens FS, Vagg RS. Studies on the metal-amide bond. VII. Metal complexes of the flexible N4 ligand N,N′-bis(2′- pyridinecarboxamide)1,2-ethane. Inorg. Chim. Acta. 1981;51:155-62.
20. Garg BS, Bhojak N, Dwivedi P, Kumar V. Copper(II) complexes of acid amide derivatives of 2-aminopyridineand an exogenous ligand. Transit. Metal. Chem. 1999;24: 463-6.
21. Anacona JR, Bravo A, Lopez ME, Antibacterial Activity of Cefoperazone Metal Complexes. Lat. Am. J. Pharm. 2012;31:27-31.
22. Franchini GC, Giusti A, Preti C, Tosi L, Zannini P. Coordinating ability of methylpiperidine dithiocarbamates towards platinum group metals. Polyhedron, 1985, 9, 1553-1558.
23. Castillo M, Criado JJ, Macias B, Vaquero MV. Chemistry of dithiocarbamate derivatives of amino acids. I. Study of some dithiocarbamate derivatives of linear α-amino acids and their nickel(II) complexes. Inorg. Chim. Acta. 1986;124:127-32.
24. El-Aziz AOA, El-Dars FM, Radowan AA. Novel all-solid contact Copper (II) - selective sensor based on Cefoperazone and poly(3,4-ethylenedioxythiophene) (PEDOT) as conducting polymer. Journal of Inventions in Biomedical and Pharmaceutical Sciences (JIBPS). 2016;1:24-31.
25. Shungu, DL, Tutlane V, Gadebusch HH. Multicenter evaluation of the proposed quality control limits and interpretive zone standards for in vitro susceptibility testing with norfloxacin. J. Clin. Microbiol. 1983;18:988-91.
26. Shungu DL, Weinberg E, Gadebusch, HH. Tentative interpretive standards for disk diffusion susceptibility testing with norfloxacin (MK-0366, AM-715). Antimicrob. Agents Chemother. 1983;23:256-60.

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Details

Primary Language	English
Journal Section	Articles
Authors	Mehmet Emin Çınar This is me 0000-0002-9822-0946 Taner Erdoğan 0000-0001-7294-0331 Ayşegül Gölcü 0000-0001-5228-1682
Project Number	105T371
Publication Date	May 31, 2021
Submission Date	April 16, 2020
Acceptance Date	January 14, 2021
Published in Issue	Year 2021 Volume: 8 Issue: 2

Cite

Vancouver	Çınar ME, Erdoğan T, Gölcü A. Cefoperazone metal complexes and their antimicrobial investigations. JOTCSA. 2021;8(2):375-90.

Cited By

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Journal of Drug Delivery Science and Technology

https://doi.org/10.1016/j.jddst.2022.103328

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