ANTIMICROBIAL EFFECT OF ORGANOTIN COMPOUNDS DERIVED FROM PHENOLIC SCHIFF BASES

Ane Francielly da Silva Santos; José Roberto da Silveira Maia

doi:10.18540/jcecvl5iss5pp0452-0459

Auteurs

Ane Francielly da Silva Santos Federal Institute of Mato Grosso
José Roberto da Silveira Maia Universidade federal de Viçosa https://orcid.org/0000-0001-5715-8763

DOI :

https://doi.org/10.18540/jcecvl5iss5pp0452-0459

Mots-clés :

Organotin(IV) compounds, Characterization, Antimicrobial effect, Bactericide

Résumé

Several organotin(IV) derivatives of phenolic Schiff bases were prepared and investigated by spectroscopic methods. These compounds were bioassayed to evaluate their bacterial effect against Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli and Salmonella typhimurium) microorganisms. Dimeric and monomeric compounds were characterized by infrared in solid state. Metallic centers having penta-, hexa-, and heptacoordination were identified by multinuclear NMR (¹H, ¹³C and ¹¹⁹Sn) in solution. The di- and triorganotin(IV) derivatives were also investigated by conductimetric measurements in methanol, elemental analysis and melting point. The bioassay of these tin(IV) compounds showed that the best resulting activity was against S. aureus for the triphenyltin(IV) phenolic Schiff base derivatives, presenting MICs of 1.1 µM (0.6 mg mL^-1) and 2.2 µM (1.3 mg mL^-1).

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Bibliographies de l'auteur

Ane Francielly da Silva Santos, Federal Institute of Mato Grosso

Química / Química Inorgânica

José Roberto da Silveira Maia, Universidade federal de Viçosa

Departamento de Química / Química Inogânica

Références

ABDALLAH, S. M. et al. Spectroscopic study of molecular structures of novel Schiff base derived from o-phthaldehyde and 2-aminophenol and its coordination compounds together with their biological activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 73, n. 5, p. 833-840, 2009. ISSN 1386-1425. Available at: http://www.sciencedirect.com/science/article/pii/S1386142509001620.

ABDEL AZIZ, A. A. et al. Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M(II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure, v. 1010, p. 130-138, 2012/02/29/ 2012. ISSN 0022-2860. Available at: http://www.sciencedirect.com/science/article/pii/S0022286011009264.

ALAGHAZ, A.-N. M. A. et al. Synthesis, spectroscopic identification, thermal, potentiometric and antibacterial activity studies of 4-amino-5-mercapto-S-triazole Schiff’s base complexes. Journal of Molecular Structure, v. 1087, p. 60-67, 2015. ISSN 0022-2860. Available at: https://www.sciencedirect.com/science/article/pii/S002228601500054X.

BARNES, J. M.; STONER, H. B. The toxicology of tin compounds. Pharmacological Reviews, v. 11, n. 2, p. 211-231, 1959. ISSN 0031-6997. Available at: Go to ISI://A1959WT75100003.

BELTRÁN, H. I. et al. Synthesis and characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures. Journal of Inorganic Biochemistry, v. 101, n. 7, p. 1070-1085, 2007/07/01/ 2007. ISSN 0162-0134. Available at: http://www.sciencedirect.com/science/article/pii/S0162013407000724.

CHANDRA, S.; SHARMA, A. K. Nickel(II) and copper(II) complexes with Schiff base ligand 2,6-diacetylpyridine bis(carbohydrazone): Synthesis and IR, mass, 1H NMR, electronic and EPR spectral studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 72, n. 4, p. 851-857, 2009. ISSN 1386-1425. Available at: http://www.sciencedirect.com/science/article/pii/S1386142508006707.

CHANS, G. M. et al. Synthesis and biological activity of trinuclear seven-coordinated tin(IV) complexes derived from tridentate ligands and trimesic acid. Journal of Coordination Chemistry, v. 68, n. 20, p. 3741-3758, 2015.

DAS, V. G. K. et al. Synthesis, spectroscopic study, and x-ray crystal structure of bis[3-(2-pyridyl)-2-thienyl-C,N]diphenyltin(IV): the first example of a six-coordinate tetraorganotin compound. Organometallics, v. 6, n. 1, p. 10-14, 1987/01/01 1987. ISSN 0276-7333. Available at: https://doi.org/10.1021/om00144a003.

DEÁK, A. et al. Synthesis and Structural Characterization of Tin(IV) N-nitroso-N-phenylhydroxylaminato Complexes: Crystal Structures of Sn(O2N2Ph)4, Ph2Sn(O2N2Ph)2 and [Me2Sn(O2N2Ph)2]2. European Journal of Inorganic Chemistry, v. 2000, n. 1, p. 127-132, 2000. ISSN 1434-1948. Available at: https://onlinelibrary.wiley.com/doi/abs/10.1002/%28SICI%2910990682%28200001%292000%3A1%3C127%3A%3AAIDEJIC127%3E3.0.CO%3B2-Q.

DUBEY, R. K.; SINGH, A. P. Dimeric and monomeric six-coordinate tin(IV) complexes: synthesis and spectral (IR, NMR (¹H, 13C, 119Sn), TOF-MS, and ESI-MS) studies. Journal of Coordination Chemistry, v. 66, n. 12, p. 2201-2207, 2013. ISSN 00958972. Available at: http://search.ebscohost.com/login.aspx?direct=true&d=aph&AN=88960534&lang=pt-br&site=ehost-live &authtype=ip,cookie,uid.

GEARY, W. J. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, v. 7, p. 81-122, 1971.

GIELEN, M. Tin-based antitumour drugs. Coordination Chemistry Reviews, v. 151, p. 41-51, Jun 1996. ISSN 0010-8545. Available at: Go to ISI://WOS:A1996UV86400003.

HU, X. M. et al. Synthesis, crystal structures, and antimicrobial activity of copper(II) and zinc(II) complexes derived from 2-bromo-4-chloro-6-[(2-morpholin-4-ylethylimino)methyl]phenol. Russian Journal of Coordination Chemistry, v. 42, n. 6, p. 418-422, June 01 2016. ISSN 1608-3318. Available at:https://doi.org/10.1134/S107032841605002X.

NAKAMOTO, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 5th. New York: John Wiley & Sons Inc., 1997. 385 ISBN ISBN 0-471-16392-9.

NATH, M. et al. New triorganotin (IV) derivatives of dipeptides as models for metal–protein interactions: Synthesis, structural characterization and biological studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 63, n. 1, p. 66-75, 2006/01/01/ 2006. ISSN 1386-1425. Available at :http://www.sciencedirect.com/science/article/pii/S1386142505002131.

NATH, M. et al. New di- and triorganotin(IV) derivatives of tyrosinylphenylalanine as models for metal-protein interactions: Synthesis and structural characterization. Crystal structure of Me2Sn(Tyr-Phe) center dot MeOH. Journal of Organometallic Chemistry, v. 693, n. 15, p. 2541-2550, Jul 2008. Available at: Go to ISI://000257290900012.

NCCLS. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. In: (Ed.). NCCLS document M27-A2. Approved Standard - Second Edition. Pennsylvania, USA: Wayne, v.22, 2002. ISBN ISBN 1-56238-469-4.

NCCLS. Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. In: (Ed.). NCCLS document M7-A6. Pennsylvania, USA, 2003. ISBN ISBN 1-56238-486-4.

POLLER, R. C. The Chemistry of Organotin Compounds. New York: Academic Press, 1970.

ROY, M. et al. Synthesis, characterization, crystal structures and in vitro antimicrobial activities of triorganotin(IV) complexes of azo-dicarboxylates. Inorganica Chimica Acta, v. 426, n. 0, p. 89-98, 2015. ISSN 0020-1693. Available at: http://www.sciencedirect.com/science/article/pii/S0020169314007294.

SANTOS, A. F. D. S. et al. Novel Zinc(II) of phenol Schiff bases: synthesis, characterisation, crystal structure and antimicrobial activity derivatives. The Journal of Engineering and Exact Sciences, v. 4, n. 1, p. 0019-0027, 2018. ISSN ISSN 2527-1075.

SARKAR, B. et al. Potentiality of organotin(IV) compounds in the control of foliar blight disease of wheat (Triticum aestivum) caused by Bipolaris sorokiniana. Archives of Phytopathology and Plant Protection, v. 44, n. 18, p. 1754-1769, Nov 2011 2011.

SINGH, H. L.; SINGH, J. Synthesis, spectral, 3D molecular modeling and antibacterial studies of dibutyltin (IV) Schiff base complexes derived from substituted isatin and amino acids. Natural Science, v. Vol.04No.03, p. 9, 2012. Available at: //www.scirp.org/journal/PaperInformation.aspx? PaperID=18067.

TAVMAN, A.; BOZ, I.; BIRTEKSÖZ, A. S. Spectral characterization and antimicrobial activity of 2-(5-chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols and their zinc(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 77, n. 1, p. 199-206, 2010. ISSN 1386-1425. Available at: http://www.sciencedirect.com/science/article/pii/S1386142510002593.

WASI, N. et al. Synthesis of metal complexes of antimalarial drugs and in vitro evaluation of their activity against plasmodium falciparum. Inorganica Chimica Acta, v. 135, n. 2, p. 133-137, 1987/02/01/ 1987. ISSN 0020-1693. Available at: http://www.sciencedirect.com/science/article/pii/S0020169300832776.

ZACCHINO, S. A.; GUPTA, M. P. Manual de técnicas in vitro para la deteccíon de compuestos antifúngicos. Corpus Libros Médicos y Científicos, 2007. ISBN 978-950-9030-40-4.