Evaluation of Antimicrobial Effect against Some Microorganisms and Apoptotic Activity against Candida Species of New Vanillin Derivatives

Öz

Eleven vanillin derivatives was synthesized, characterized successfully and their antibacterial and anticandidal properties were investigated on seven bacterial species and four candida species. These bacterial species are Staphylococcus aureus, Enterococcus faecalis, Listeria monocytogenes, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, and Bacillus subtilis and candidal species are Candida albicans, Candida glabrata, Candida krusei and Candida parapsilosis. Most of the synthesized compounds were showed good activity against studied microorganisms compared with Chloramphenicol. Compounds 2c, 2d and 2k were exhibited remarkable antibacterial activities especially on Escherichia coli. In addition, Klebsiella pneumoniae, Pseudomonas aeruginosa and Bacillus subtilis were found to be the most susceptible species amongst the investigated microorganisms

Anahtar Kelimeler

• Antimicrobial,Vanillin,Schiff base

Kaynakça

1. 1. Hoiby, N, Bjarnsholt, T, Givskov, M, Molin, S, Ciofu, O. 2010. Antibiotic resistance of bacterial biofilms. International Journal of Antimicrobial Agents; 35: 322-332.
2. 2. Wright, GD. 2005. Bacterial resistance to antibiotics: Enzymatic degradation and modification. Advanced Drug Delivery Reviews; 57: 1451-1470.
3. 3. Fisher, JF, Meroueh, SO, Mobashery, S. 2011. Bacterial resistance to β-lactam antibiotics: compelling opportunism compelling opportunity, Chemical Reviews; 105: 395−424.
4. 4. Kuete, V, Alibert-Franco, S, Eyong, KO, Ngameni, B, Folefoc, GN, Nguemeving, JR. 2011. Antibacterial activity of some natural products against bacteria expressing a multidrug resistant phenotype, International Journal of Antimicrobial Agents; 37: 156-161.
5. 5. Stavri, M, Piddock, LJV, Gibbons, S. 2007. Bacterial efflux pump inhibitors from natural resources. Journal of Antimicrobial Chemotheraphy. 59(6): 1247-1260.
6. 6. Sun, J, Yin, Y, Sheng, GH, Yang, ZB, Zhu, HL. 2013. Synthesis, molecular modelling and structural characterization of vanillin derivatives as antimicrobial agents. Journal of Molecular Structure; 1039: 214-218.
7. 7. Harini, ST, Kumar, HV, Rangaswamy, J, Naik, N. 2012. Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core. Bioorganic & Medicinal Chemistry Letters; 22: 7588-7592.
8. 8. Kamat, JP, Ghosh, A, Devasagayam, TPA. 2000. Vanillin as an antioxidant in rat liver mitochondria: Inhibition of protein oxidation and lipid peroxidation induced by photosensitization, Molecular and Cellular Biochemistry; 209:47-53.

9. 9. Naz, H, Tarique, M, Khan, P, Luqman, S, Ahamad, S, Islam, A, Ahmad, F, Hassan, MI. 2018. Evidence of vanillin binding to CAMKIV explains the anti-cancer mechanism in human hepatic carcinoma and neuroblastoma cells. Molecular and Cellular Biochemistry; 438: 35-45.
10. 10. Jung, HJ, Song, YS, Kim, K, Lim, CJ, Park, EH. 2010. Assessment of the anti-angiogenic, anti-inflammatory and anti-nociceptive properties of ethyl vanillin. Archives of Pharmacal Research; 33:309-316.
11. 11. King, AA, Shaughnessy, DT, Mure, K. 2007. Antimutagenicity of cinnamaldehyde and vanillin in human cells: Global gene expression and possible role of DNA damage and repair. Mutation Research; 616: 60-69.
12. 12. Segura, JL, Mancheno, MJ, Zamora, F. 2016. Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications. Chemical Society Reviews; 45: 5635-5671.
13. 13. Vitago, PA, Tamburini, S. 2004. The challenge of cyclic and acyclic schiff bases and related derivatives. Coordination Chemistry Reviews; 248: 1717-2128.
14. 14. Guerriero, P, Vigato, PA, Fenton, DE, Hellier, PC. 1992. Synthesis and Application of Macrocyclic and Macroactclic Schiff bases. Acta Chemica Scandinavica; 46: 1025-1046.
15. 15. Zayed, EM, Zayed, MA. 2015. Synthesis of novel schiff’s bases of highly potential biological activities and their structure investigation. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 143: 81-90.
16. 16. Ceylan, S. 2016. Synthesis and biological evaluation of new Mannich and Schiff bases containing 1,2,3-triazole and 1,3,4-oxadiazole nucleus. Medicinal Chemistry Research; 25: 1958-1970.
17. 17. Maja, M, Milan, C, Zrinusic, Z. 2012. Synthesis and antioxidant evaluation of Schiff bases derived from 2,6-pyridinedicarboxylic acid, Letters in Organic Chemistry; 9: 401-410.
18. 18. Gomez, RC, Witter, SK, Hieke, M. 2014. Vanillin-derived antiproliferative compounds influence Plk1 activity, Bioorganic and Medicinal Chemistry Letters; 24: 5063-5069.
19. 19. Engeland, M, Luc, JW, Frans, CS, Chris, PM. 1998. Annexin V-Affinity Assay: A Review on an Apoptosis Detection System Based on Phosphatidylserine Exposure. Cytometry; 31: 1-9.
20. 20. Faria, NCG, Kim, JH, Goncalves, LAP. 2011. Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus. Letters in Applied Microbiology; 52: 5.