Sulfonate Group Containing Schiff Base Ligand and Their Transition Metal Complexes: Synthesis, Structural Characterization and Antimicrobial Activity Studies

Öz

In this study, H4L Schiff base ligand which can form stable complexes with 4,4′-Diamino-2,2′-stilbenedisulfonic acid compound having primary diamine and disulfonic acid group in its molecular structure was synthesized. Cu(II), Zn(II) and Cd(II) complex compounds of the H4 Lligand were synthesized. Molecular structures of the compounds obtained were characterized using analytical and spectroscopic methods. Gram positive(5), gram negative(6), probiotic bacteria(2) antimicrobial and antifungal activities (MIC, MBC) of all compounds were studied. MIC values of the compounds on indicator bacteria at concentrations of 500, 250, 62.5, 31.2, 15.63 and 7.81 μg/mL, 250 mg/mL for H4L, 31.5 mg/mL for [Cu2H2L(CH3COO)2(H2O)2], 62.5 mg/mL for [Cd2H2LCl2(H2O2] and 125 mg/mL for [Zn2H2L(CH3COO)2(H2O)2], the complexes were determined to be more effective than the ligand. Bactericidal effects were determined in the MBC test at concentrations of 500-250 mg/mL. In the agar well diffusion test, the compounds were tested only at 500 mg/ml and different inhibition diameters were determined.

Anahtar Kelimeler

• Complex compounds
• antimicrobial activity
• gram positive

Sülfonat Grubu İçeren Schiff Bazı Ligandı ve Geçiş Metal Kompleksleri: Sentezi, Yapısal Karakterizasyonları ve Antimikrobiyal Aktivitelerinin İncelenmesi

Öz

Bu çalışmada, molekül yapısında primer diamin ve disülfonik asit grubu bulunduran 4,4′-Diamino-2,2′-stilbendisülfonik asit bileşiği ile 2,4-dihidroksi benzaldehit kullanılarak kararlı kompleksler oluşturabilen H4L Schiff bazı ligandı sentezlenmiştir. H4L ligandının Cu(II), Zn(II) ve Cd(II) kompleks bileşikleri sentezlenmiştir. Elde edilen bileşiklerin molekül yapıları analitik ve spektroskopik yöntemler kullanılarak karakterize edilmiştir. Tüm bileşiklerin gram pozitif (5), gram negatif (6) ve probiyotik bakterileri (2) kullanılarak antimikrobiyal aktiviteleri ve antifungal aktivite (MIC, MBC) çalışmaları yapılmıştır. Bileşiklerin 500, 250, 62.5, 31.2, 15.63 ve 7.81 μg/mL konsantrasyonlarda indikatör bakterileri üzerine MIC değerleri, H4L için 250 mg/mL, [Cu2H2L(CH3COO)2(H2O)2] için 31.5 mg/mL, [Cd2H2LCl2(H2O)2] için 62.5 mg/mL, [Zn2H2L(CH3COO)2(H2O)2] için 125 mg/mL olarak komplekslerin ligantdan daha etkili olduğu belirlenmiştir. MBC testinde 500-250 mg/mL konsantrasyonlarında bakterisid etki belirlenmiştir. Agar kuyu difüzyon testinde ise bileşikler sadece 500 mg/ml’de test edilmiş ve farklı inhibisyon çapları belirlenmiştir.

Anahtar Kelimeler

• Kompleks bileşikler
• antimikrobiyal aktivite
• gram pozitif

Kaynakça

1. Al-Qadsy I., Saeed WS., Al-Odayni A., Al-Faqeeh L.A.S., Alghamdi A.A., Farooqui M., 2020. Novel Metformin-Based Schiff Bases: Synthesis, Characterization, and Antibacterial Evaluation. Materials 13:514.
2. Atahan, A., Durmus S., 2015. “1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: Selective synthesis and photophysical properties” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 144:61–67.
3. Aytar M., Oryaşın E., Başbülbül G., Bozdoğan B., 2019. Agar Well Difüzyon Yönteminde Standardizasyon Çalışması. JONAS 2 (2): 138-145.
4. Bagul U.S., Sivakumar S.M., 2016. Antibiotic Susceptibility Testing: A Review On Current Practices. Int J Pharm 6(3): 11-17.
5. Bharti, S., Choudhary, M., Mohan, B., Rawat, S.P., Sharma, S.R., Ahmad K., 2018. “Syntheses, spectroscopic characterization, SOD-like properties and antibacterial activities of dimer copper (II) and nickel (II) complexes based on imine ligands containing 2-aminothiophenol moiety: X-ray crystal structure determination of disulfide Schiff bases” J. Mol. Struct. 1164:137-154.
6. Foni, B.B., Tapashi, G.R., Atiar, R., and Talha, B.E. (2014). An in vitro antibacterial and antifungal effects of cadmium(II) complexes of hexamethyltetraazacyclotetradecadiene and isomers of its saturated analogue. Asian Pac. J. Trop. Med. 7(Suppl 1): S534-S539.
7. Gonelimali FD., Lin J., Miao W., Xuan J., Charles F., Chen M., Hatab SR. 2018. Antimicrobial Properties and Mechanism of Action of Some Plant Extracts Against Food Pathogens and Spoilage Microorganisms. Frontiers in Microbiology 9:1639.
8. Hossain Md.M., Bashar Md.A., Khan Md.N., Roy PK., Ali Md.S., Farooque Md.A., 2018. Preparation, Physical Characterization and Antibacterial Activity of Ni (II), Cu (II), Co (II), Cd (II), Zn (II) and Cr (III) Schiff Base Complex Compounds. Science Journal of Chemistry 6(2): 17-23.

9. Kus F., Tasaltin C., Albakour M. Gürek AG., Gürol İ., 2019. Macromolecular hexa-asymmetric zinc(II) phthalocyanines bearing triazole-modified triphenylene core: Synthesis, spectroscopy and analysis towards volatile organic compounds on Surface Acoustic Wave devices. J. Porphyrins Phthalocyanines 23: 477–488.
10. Lalitha, M.K. (2009) Manual on Antimicrobial Susceptibility Testing. (Under the Auspices of Indian Association of Medical Microbiologists). American Society for Microbiology, Washington DC.
11. Li, B., Webster, T.J., 2018. “Bacteria Antibiotic Resistance: New Challenges and Opportunities for Implant-Associated Orthopaedic Infections” J. Orthop Res. 36(1): 22–32.
12. Rice, LB. 2006. “Unmet medical needs in antibacterial therapy” Biochem Pharmacol 71(7):991–5.
13. Salas H., Gutiérrez-Bouzán C., López-Grimau V., Vilaseca M., 2019. Respirometric Study of Optical Brighteners in TextileWastewater. Materials12:785.
14. Saranya J., Kirubavathy SJ., Chitra S., Zarrouk A., Kalpana K., Lavanya K., Ravikiran B., 2020. Tetradentate Schiff Base Complexes of Transition Metals for Antimicrobial Activity. Arabian Journal for Science and Engineering 45:4683–4695.
15. Shaikha, A.B., Barachea, U.B., Anuseb, M.A., Gaikwada, S.H., 2016. “4-(4’-Nitrobenzylideneimino)-3-methyl-5-mercapto-1, 2, 4-triazole, A New Chromogenic Reagent for Extractive Spectrophotometric Determination of Copper (II) in Pharmaceutical and Alloy Samples” S. Afr. J. Chem., 69, 157–165.
16. Tunçel, M., Serin, S., 2003. “Synthesis and Characterization of Copper(II), Nickel(II), and Cobalt(II) Chelates with Tridentate Schiff Base Ligands Derived from 4-Amino-5-hydroxynaphthalene-2,7-disulfonic Acid” Synth React Inorg M. 33:985–998.
17. Wan, M., Hua, L., Zeng Y., Jiao, P., Xie, D., Tong Z., Wu G., Zhou, Y., Tang Q., Mo, F., 2017. Synthesis and properties of novel stilbene-twelve alkyl quaternary ammonium salts as antibacterial optica whitening agents. Cellulose 24:3209–3218.