Synthesis, spectroscopic and thermogravimetric interpretations of UO2(II), ZrO(II), Zr(IV), VO(II) and V(V) ciprofloxacin antibiotic drug complexes

Albedair, Lamia A.

doi:10.2478/pjct-2021-0007

Abstract

New five ciprofloxacin (CIP) complexes of dioxouranium(II), oxozirconium(II), zirconium(IV), oxovanadium(II) and vanadium(IV) in the proportion 1:2 have been prepared using CIP as a drug chelate with UO₂(NO₃)₂. 6H₂O, ZrOCl₂. _8H2O, ZrCl₄, VOSO₄. xH₂O and V₂O₅ respectively. The CIP complexes have been characterized based on the elemental analysis, molar conductance, magnetic, (FTIR & ¹HNMR) spectral and thermal studies. The molar conductance studies of the synthesized complexes in DMSO solvent with concentration of 10^–3 M indicate their non-electrolytic properties. At room temperature, the magnetic moment measurements revealed a diamagnetic behavior for all CIP prepared complexes. The different formulas of the new complexes can be represented as [UO₂(CIP)₂(NO₃)₂] (I), [VO(CIP)₂(SO₄)(H₂O)] (II), [V₂(O)(O₂)₂(CIP)₂] (III), [Zr(O)(CIP)₂(Cl)₂] (IV), and [Zr(CIP)₂(Cl)₄] (V). The thermal analysis data of the complexes indicates the absence of coordinated water molecules except for vanadyl(II) complex (II). The CIP chelate is a uni-dentate ligand coordinated to the mentioned metal ion through terminal piperazinyl nitrogen. The transmission electron microscopy (TEM) investigation confirms the nano-structured form of the complexes.

References

1. Shen, G.Z., Zou, G.H., Li, H.Y. & Zou, Y.L. (2019). Crystal structure and antibacterial activity of polyoxometalate cobalt-ciprofloxacin complex. J. Mol. Struct., 1198, 126831. DOI: 10.1016/j.molstruc.2019.07.078.10.1016/j.molstruc.2019.07.078
Search in Google Scholar Back to article
2. Ma, J., Xiong, Y., Dai, X. & Yu, F. (2020). Coadsorption behavior and mechanism of ciprofloxacin and Cu(II) on graphene hydrogel wetted surface. Chem. Engineering J., 38015, 122387. DOI: 10.1016/j.cej.2019.122387.10.1016/j.cej.2019.122387
Search in Google Scholar Back to article
3. George, J.M., Priyanka, R.N. & Mathew, B. (2020). Bimetallic Ag–Au nanoparticles as pH dependent dual sensing probe for Mn(II) ion and ciprofloxacin. Microchemical J., 155, 104686. DOI: 10.1016/j.microc.2020.104686.10.1016/j.microc.2020.104686
Search in Google Scholar Back to article
4. Kumar, M., Sodhi, K.K., Singh, P., Agrawal, P.K. & Singh, D.K. (2019). Synthesis and characterization of antibiotic-metal complexes [FeCl3(L1)2H2O and Ni(NO3)2(L2)2H2O] and enhanced antibacterial activity. Environ. Nanotechnol., Monitoring & Management, 11, 100209. DOI: 10.1016/j.enmm.2019.100209.10.1016/j.enmm.2019.100209
Search in Google Scholar Back to article
5. Drevenšek, P., Ulrih, N.P., Majerle, A. & Turel, I. (2006). Synthesis, characterization and DNA binding of magnesium–ciprofloxacin (cfH) complex [Mg(cf)2]·2.5H2O. J. Inorg. Biochem., 100, 1705–1713. DOI: 10.1016/j.jinorgbio.2006.06.003.10.1016/j.jinorgbio.2006.06.00316876251
Search in Google Scholar Back to article
6. Turel, I., Šonc, A., Zupančič, M., Sepčić, K. & Turk, T. (2000). Biological activity of some magnesium(II) complexes of quinolones. Met. Based Drugs, 7, 101–104.10.1155/MBD.2000.101236520118475931
Search in Google Scholar Back to article
7. Turel, I., Živec, P., Pevec, A., Tempelaar, S. & Psomas, G. (2008). Compounds of antibacterial agent ciprofloxacin and magnesium – crystal structures and molecular modeling calculations. Eur. J. Inorg. Chem., 23, 3718–3727. DOI: 10.1002/ejic.200800338.10.1002/ejic.200800338
Search in Google Scholar Back to article
8. Al-Mustafa, J. & Taha, Z.A. (2011). Thermodynamics of the complexation of ciprofloxacin with calcium and magnesium perchlorate. Thermochim. Acta, 521, 9–13. DOI: 10.1016/j. tca.2011.03.033.
Search in Google Scholar Back to article
9. Zupančič, M., Cerc Korošec, R. & Bukovec, P. (2001). The thermal-stability of ciprofloxacin complexes with magnesium (II), zinc (II) and cobalt (II). J. Therm. Anal. Calorim., 63, 787–795. DOI: 10.1023/a:1010100423044.10.1023/A:1010100423044
Search in Google Scholar Back to article
10. Breda, S.A., Jimenez-Kairuz, A.F., Manzo, R.H. & Oli-vera, M.E. (2009). Solubility behavior and biopharmaceutical classification of novel high-solubility ciprofloxacin and norfloxacin pharmaceutical derivatives. Int. J. Pharmaceut., 371, 106–113. DOI: 10.1016/j.ijpharm.2008.12.026.10.1016/j.ijpharm.2008.12.02619150493
Search in Google Scholar Back to article
11. Shaikh, A.R., Giridhar, R., Megraud, F. & Yadav, M.R. (2009). Metalloantibiotics: Synthesis, characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter Pylori. Acta Pharm., 59, 259–271. DOI: 10.2478/v10007-009-0027-6.10.2478/v10007-009-0027-619819823
Search in Google Scholar Back to article
12. Turel, I., Golobič, A., Klavžar, A., Pihlar, B., Buglyó, P., Tolis, E., Rehder, D. & Sepčić, K. (2003). Interactions of oxovanadium(IV) and the quinolone family member—ciprofloxacin. J. Inorg. Biochem., 95, 199–207. DOI: 10.1016/S0162-0134(03)00123-5.10.1016/S0162-0134(03)00123-5
Search in Google Scholar Back to article
13. Anacona, J.R. & Toledo, C. (2001). Synthesis and antibacterial activity of metal complexes of ciprofloxacin. Trans. Met. Chem., 26, 228–231. DOI: 10.1023/A:1007154817081.10.1023/A:1007154817081
Search in Google Scholar Back to article
14. Psomas, G. (2008). Mononuclear metal complexes with ciprofloxacin: Synthesis, characterization and DNA-binding properties. J. Inorg. Biochem., 102, 1798–1811. DOI: 10.1016/j. jinorgbio.2008.05.012.
Search in Google Scholar Back to article
15. Lopez-Gresa, M.P., Ortiz, R., Perelló, L., Latorre, J., Liu-González, M., García-Granda, S., Pérez-Priede, M. & Canton, E. (2002). Interaction of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin). Spectroscopic and X-ray structural characterization. Antibacterial studies. J. Inorg. Biochem., 92, 65–74. DOI: 10.1016/S0162-0134(02)00487-7.10.1016/S0162-0134(02)00487-7
Search in Google Scholar Back to article
16. Zupančič, M., Cerc Korošec, R. & Bukovec, P. (2001). The thermal-stability of ciprofloxacin complexes with magnesium (II), zinc (II) and cobalt (II). J. Therm. Anal. Calorim., 63, 787–795. DOI: 10.1023/a:1010100423044.10.1023/A:1010100423044
Search in Google Scholar Back to article
17. Hernandez-Gil, J., Perello, L., Ortiz, R., Alzuet, G., Gonzalez-Alvarez, M. & Liu-Gonzalez, M. (2009). Synthesis, structure and biological properties of several binary and ternary complexes of copper(II) with ciprofloxacin and 1,10 phenanthroline. Polyhedron, 28, 138–144. DOI: 10.1016/j.poly.2008.09.018.10.1016/j.poly.2008.09.018
Search in Google Scholar Back to article
18. Wallis, S.C., Gahan, L.R., Charles, B.G., Hambley, T.W. & Duckworth, P.A. (1996). Copper (II) complexes of the fluoroquinolone antimicrobial ciprofloxacin: Synthesis, X-ray structural characterization and potentiometric study. J. Inorg. Biochem., 62, 1–16. DOI: 10.1016/0162-0134(95)00082-8.10.1016/0162-0134(95)00082-8
Search in Google Scholar Back to article
19. Turel, I. & Leban, I. (1994). Bukovec, N. Synthesis, characterization, and crystal structure of a copper(II) complex with quinolone family member (ciprofloxacin): Bis(1)-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazin-1ylquinoline-3-carbox-ylate) copper(II) chloride hexahydrate. J. Inorg. Biochem., 56, 273–282. DOI: 10.1016/0162-0134(94)85107-7.10.1016/0162-0134(94)85107-7
Search in Google Scholar Back to article
20. Jiménez-Garrido, N., Perelló, L., Ortiz, R., Alzuet, G., González-Álvarez, M., Cantón, E., Liu-González, M., García Granda, S. & Pérez-Priede, M. (2005). Antibacterial studies, DNA oxidative cleavage, and crystal structures of Cu(II) and Co(II) complexes with two quinolone family members, ciprofloxacin and enoxacin. J. Inorg. Biochem., 99, 677–689. DOI: 10.1016/j.jinorgbio.2004.11.016.10.1016/j.jinorgbio.2004.11.01615708788
Search in Google Scholar Back to article
21. Drevenšek, P., Zupančič, T., Pihlar, B., Jerala, R., Kolitsch, U., Plaper, A. & Turel, I. (2005). Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of L-histidine: Comparison of biological activities of various copper–ciprofloxacin compounds. J. Inorg. Biochem., 99, 432–442. DOI: 10.1016/j.jinorgbio.2004.10.018.10.1016/j.jinorgbio.2004.10.01815621275
Search in Google Scholar Back to article
22. Uivarosi, V., Badea, M., Olar, R., Marinescu, D., Nicolescu, T.O. & Nitulescu, G.M. (2011). Thermal degradation behavior of some ruthenium complexes with fluoroquinolone derivatives as potential antitumor agents. J. Therm. Anal. Calorim., 105, 645–650. DOI: 10.1007/s10973-010-1222-x.10.1007/s10973-010-1222-x
Search in Google Scholar Back to article
23. Tanimoto, M.K., Dias, K., Dovidauskas, S. & Nikolaou, S. (2012). Tuning the reaction products of ruthenium and ciprofloxacin for studies of DNA interactions. J. Coord Chem., 65, 1504–1517. DOI: 10.1080/00958972.2012.675434.10.1080/00958972.2012.675434
Search in Google Scholar Back to article
24. Vieira, L.M.M., de Almeida, M.V., Lourenço, M.C.S., Bezerra, F.A.F.M. & Fontes, A.P.S. (2009). Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones. Eur. J. Med. Chem., 44, 4107–4111. DOI: 10.1016/j.ejmech.2009.05.001.10.1016/j.ejmech.2009.05.001
Search in Google Scholar Back to article
25. Čurman, D., Živec, P., Leban, I., Turel, I., Polishchuk, A., Klika, K.D., Karaseva, E. & Karasev, V. (2008). Spectral properties of Eu(III) compound with antibacterial agent cip-rofloxacin (cfqH). Crystal structure of [Eu(cfqH)(cfq)(H2O)4] Cl2· 4.55H2O. Polyhedron, 27, 1489–1496. DOI: 10.1016/j. poly.2008.01.014.
Search in Google Scholar Back to article
26. Geary, W.J. (1971). The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev., 7, 81. DOI: 10.1016/S0010-8545(00)80009-0.10.1016/S0010-8545(00)80009-0
Search in Google Scholar Back to article
27. Nakamoto, K. (2009). Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part A: Theory and Applications in Inorganic Chemistry, 6^th, John Wiley & Sons.10.1002/9780470405888
Search in Google Scholar Back to article
28. Mansingh, P.S., Mohanty, R.R., Jena, S. & Dash, K.C. (1996). Synthesis and characterization of dioxouranium(VI) and thorium(IV) complexes of 2-(2’-hydroxyphenyl) benzimidazole and 2-(2-pyridyl benzoxazole. Ind. J. Chem. 35A, 479–482.
Search in Google Scholar Back to article
29. Di Bella, S., Lanza, G., Gulino, A. & Fragalà, I. (1996). Electronic Structure of Bis(2,4-pentanedionato-O,O‘)oxovanadium(IV). A Photoelectron Spectroscopy, Electronic Spectroscopy, and ab Initio Molecular Orbital Study. Inorg. Chem., 35(13), 3885–3890. DOI: 10.1021/ic951457q.10.1021/ic951457q11666579
Search in Google Scholar Back to article
30. Nakanishi, K. & Solomon, P.H. (1977). “Infrared Absorption Spectroscopy”, 2^nd, Holden-Day, Inc., USA.
Search in Google Scholar Back to article
31. Selbin, J. (1965). The Chemistry of Oxovanadium(IV). Chem. Rev., 65, 153–175. DOI: 10.1021/cr60234a001.10.1021/cr60234a001
Search in Google Scholar Back to article
32. Srivastava, K.P., Jain, I.K. & Madhok, K.L. (1981). Vanadyl(V) chloride complexes of N-2 (4, 5, 6 monosubstituted pyridyl)-N′-substituted thio ureas. Proc. Indian Acad. Sci. (Chem. Sci.), 90(4), 309–316. DOI: 10.1007/BF02879405.10.1007/BF02879405
Search in Google Scholar Back to article
33. Lever, A.B.P. (1984). Electronic spectra of dⁿ ions Inorganic electronic spectroscopy. 2^nd Ed.
Search in Google Scholar Back to article

Synthesis, spectroscopic and thermogravimetric interpretations of UO2(II), ZrO(II), Zr(IV), VO(II) and V(V) ciprofloxacin antibiotic drug complexes

Abstract

Paradigm

My account