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SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES

Year 2023, , 40 - 55, 31.07.2023

Hasan Ufuk Celebioglu , Ebru Köroğlu , Recep Taş , Sevilay Günay , Yavuz Erden

https://doi.org/10.55930/jonas.1278393

Abstract

Schiff bases have been widely researched in vitro for their antimicrobial, antitumor, antiviral, antineoplastic, and antioxidant properties, owing to their strong chelating ability. Probiotics refer to “live microorganisms that, when administered in adequate amounts, confer a health benefit on the host”. Thus, this study aims to investigate the antibacterial, anticancer, and antioxidant effects of Schiff Bases N-methylene-N-phenylbenzenaminium and N-(5-oxopentylidene)-N-phenylbenzenaminium, as well as their impact on some properties of probiotic bacteria, Lactobacillus acidophilus and Lacticaseibacillus rhamnosus. Results indicate that these Schiff bases promote the growth of probiotic bacteria while inhibiting pathogenic bacteria. They demonstrate potent antibacterial and antioxidant activities, and cytotoxicity assays reveal that both compounds exert a high degree of inhibition on human colon and breast cancer cells. Additionally, there is significant modulation in auto-aggregation and surface hydrophobicity of Lactobacillus acidophilus and Lacticaseibacillus rhamnosus. In conclusion, the Schiff bases investigated in this study possess significant therapeutic potential.

Keywords

Antibacterial anticancer antioxidant Lactobacillus probiotics Schiff bases

Supporting Institution

Bartın Üniversitesi

Project Number

2020-FEN-A-006

Thanks

The authors are grateful to Chr. Hansen, Turkey for the probiotic strains. This work was partly financed by Bartin University Scientific Research Project Coordination Unit (Project No: 2020-FEN-A-006).

References

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Year 2023, , 40 - 55, 31.07.2023

Hasan Ufuk Celebioglu , Ebru Köroğlu , Recep Taş , Sevilay Günay , Yavuz Erden

https://doi.org/10.55930/jonas.1278393

Abstract

Project Number

2020-FEN-A-006

References

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  • 5. Arena, M.P., Capozzi, V., Spano, G. & Fiocco, D. (2017). The potential of lactic acid bacteria to colonize biotic and abiotic surfaces and the investigation of their interactions and mechanisms. Applied Microbiology and Biotechnology, 101(7), 2641-2657.
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  • 12. Çelebi, B., Taş, R., Akşit, A. & Celebioglu, H.U. (2020). Effects of loganic acid isolated from Vinca soneri on surface hydrophobicity and auto-aggregation of probiotic bacteria, Lactobacillus acidophilus and Lactobacillus rhamnosus. Erzincan University Journal of Science and Technology. 13(1), 115-122.
  • 13. Celebioglu, H.U., Ejby, M., Majumder, A., Kobler, C., Goh, Y.J., Thorsen, K., Schmidt, B., Flaherty, S., Hachem, M.A., Lahtinen, S.J., Jacobsen, S., Klaenhammer, T.R., Brix, S., Molhave, K. & Svensson, B. (2016). Differential proteome and cellular adhesion analyses of the probiotic bacterium Lactobacillus acidophilus NCFM grown on raffinose - an emerging prebiotic. Proteomics. 16(9), 1361-1375.
  • 14. Celebioglu, H.U., Kesici, A. & Taş, R. (2020a). Investigation of possibilities of using Nerium oleander L. extract as prebiotic for Lactobacillus acidophilus and Lactobacillus rhamnosus. Erzincan University Journal of Science and Technology. 13(3), 1147-1157.
  • 15. Celebioglu, H.U., Erden, Y., Hamurcu, F., Taslimi, P., Şentürk, O.S., Özmen, Ü.Ö., Tuzun, B. & Gülçin, İ. (2020b). Cytotoxic effects, carbonic anhydrase isoenzymes, α-glycosidase and acetylcholinesterase inhibitory properties, and molecular docking studies of heteroatom-containing sulfonyl hydrazone derivatives. Journal of Biomolecular Structure and Dynamics, 1-12.
  • 16. Celebioglu, H.U. & Svensson, B. (2018). Dietary nutrients, proteomes, and adhesion of probiotic lactobacilli to mucin and host epithelial cells. Microorganisms. 6(3).
  • 17. Charalampopoulos, D., Pandiella, S.S. & Webb, C. (2002). Growth studies of potentially probiotic lactic acid bacteria in cereal-based substrates. Journal of Applied Microbiology. 92(5), 851-859.
  • 18. Collado, M.C., Meriluoto, J. & Salminen, S. (2008). Adhesion and aggregation properties of probiotic and pathogen strains. European Food Research and Technology. 226(5), 1065-1073.
  • 19. Dagogo-Jack, I & Shaw, A.T. (2018). Tumour heterogeneity and resistance to cancer therapies. Nat Rev Clin Oncol. 15(2), 81-94.
  • 20. Das, A., Trousdale, M.D., Ren, S.J. & Lien, E.J. (1999). Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of aminohydroxyguanidine tosylate. Antiviral Research. 44(3), 201-208.
  • 21. De Souza, A.O., Galetti, F.C.S., Silva, C.L., Bicalho, B., Parma, M.M., Fonseca, S.F., Marsaioli, A.J., Trindade, A.C., Gil, R.P., Bezerra, F.S., Neto, M.A. & Oliveira, M.C. (2007). Antimycobacterial and cytotoxicity activity of synthetic and natural compounds. Quimica Nova. 30(7), 1563-1566.
  • 22. Drisko, J.A., Giles, C.K. & Bischoff, B.J. (2003). Probiotics in health maintenance and disease prevention. Alternative medicine review.8(2), 143-155.
  • 23. Durackova, Z., Mendiola, M.A., Sevilla, M.T. & Valent, A. (1999). Thiohydrazone copper(II) complexes. The relationship between redox properties and superoxide dismutase mimetic activity. Bioelectrochemistry and Bioenergetics. 48(1), 109-116.
  • 24. Fioravanti, R., Biava, M., Donnarumma, S. & Porretta, G.C. (1996). Synthesis and microbiological evaluations of (N-heteroaryl)arylmethanamines and their Schiff bases. Farmaco. 51(10), 643-652.
  • 25. Galini, M., Salehi, M., Kubicki, M., Amiri, A. & Khaleghian, A. (2017). Structural characterization and electrochemical studies of Co(II), Zn(II), Ni(II) and Cu(II) Schiff base complexes derived from 2-((E)-(2-methoxyphenylimino)methyl)-4-bromophenol; Evaluation of antioxidant and antibacterial properties. Inorganica Chimica Acta. 461, 167-173.
  • 26. Gonzalez-Rodriguez, I., Ruiz, L., Gueimonde, M., Margolles, A. & Sanchez, B. (2013). Factors involved in the colonization and survival of bifidobacteria in the gastrointestinal tract. Fems Microbiology Letters. 340(1), 1-10.
  • 27. Gupta, S. & Ravishankar, S. (2005). A comparison of the antimicrobial activity of garlic, ginger, carrot, and turmeric pastes against Escherichia coli O157 : H7 in laboratory buffer and ground beef. Foodborne Pathogens and Disease. 2(4), 330-340.
  • 28. Hajrezaie, M., Paydar, M., Zorofchian Moghadamtousi, S., Hassandarvish, P., Gwaram, N.S., Zahedifard, M., Rouhollahi, E., Karimian, H., Looi, C.Y., Ali, H.M., Majid, N.A. & Abdulla, M.A. (2014). A Schiff Base-derived copper (II) complex is a potent inducer of apoptosis in colon cancer cells by activating the intrinsic pathway. The Scientific World Journal.
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There are 63 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Hasan Ufuk Celebioglu 0000-0001-7207-2730

Ebru Köroğlu 0000-0002-0710-5716

Recep Taş 0000-0002-3743-7770

Sevilay Günay

Yavuz Erden

Project Number 2020-FEN-A-006
Publication Date July 31, 2023
Published in Issue Year 2023

Cite

APA Celebioglu, H. U., Köroğlu, E., Taş, R., Günay, S., et al. (2023). SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES. Bartın University International Journal of Natural and Applied Sciences, 6(1), 40-55. https://doi.org/10.55930/jonas.1278393
AMA Celebioglu HU, Köroğlu E, Taş R, Günay S, Erden Y. SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES. JONAS. July 2023;6(1):40-55. doi:10.55930/jonas.1278393
Chicago Celebioglu, Hasan Ufuk, Ebru Köroğlu, Recep Taş, Sevilay Günay, and Yavuz Erden. “SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES”. Bartın University International Journal of Natural and Applied Sciences 6, no. 1 (July 2023): 40-55. https://doi.org/10.55930/jonas.1278393.
EndNote Celebioglu HU, Köroğlu E, Taş R, Günay S, Erden Y (July 1, 2023) SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES. Bartın University International Journal of Natural and Applied Sciences 6 1 40–55.
IEEE H. U. Celebioglu, E. Köroğlu, R. Taş, S. Günay, and Y. Erden, “SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES”, JONAS, vol. 6, no. 1, pp. 40–55, 2023, doi: 10.55930/jonas.1278393.
ISNAD Celebioglu, Hasan Ufuk et al. “SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES”. Bartın University International Journal of Natural and Applied Sciences 6/1 (July 2023), 40-55. https://doi.org/10.55930/jonas.1278393.
JAMA Celebioglu HU, Köroğlu E, Taş R, Günay S, Erden Y. SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES. JONAS. 2023;6:40–55.
MLA Celebioglu, Hasan Ufuk et al. “SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES”. Bartın University International Journal of Natural and Applied Sciences, vol. 6, no. 1, 2023, pp. 40-55, doi:10.55930/jonas.1278393.
Vancouver Celebioglu HU, Köroğlu E, Taş R, Günay S, Erden Y. SYNTHESIS AND FUNCTIONAL PROPERTIES OF DIPHENYLAMINE-CONTAINING SCHIFF BASES. JONAS. 2023;6(1):40-55.