A Schiff Base Sensor Selective to Anions, Biological Activity and Spectral Studies

Nuray Yıldırım; Mustafa Yıldız

doi:10.18596/jotcsa.431554

Research Article

A Schiff Base Sensor Selective to Anions, Biological Activity and Spectral Studies

Year 2018, Volume: 5 Issue: 3, 1271 - 1278, 01.09.2018

Nuray Yıldırım Mustafa Yıldız

https://doi.org/10.18596/jotcsa.431554

Cited By: 6

Abstract

In this study, synthesis, characterization, anion sensor properties, and DNA binding of a benzothiazole-based Schiff base 4-bromo-2-((6-methoxybenzo[d]thiazol-2-ylimino)methyl)phenol have been investigated. The structure of the Schiff base was revealed with elemental analysis and spectroscopic methods. The colorimetric and fluorescent anion sensor properties of the Schiff base in DMSO were investigated by adding an equivalent amount of anions. In this context, the solution containing Schiff base had a color change after the addition of F^-, CN^-, AcO^-, H₂PO₄^- and OH^- anions, while the color change was not observed with the addition of Br^-, I^-, SCN^-, ClO₄^- and HSO₄^- anions. The anion-binding power of the compound was found to be F^->OH^->AcO^->CN^->H₂PO₄^- using UV-Vis spectrophotometry, respectively. The antimicrobial activity of the compound was investigated against some microorganisms. The compound showed activity against bacteria and yeast. Schiff base showed a similar effect against both bacteria and yeast. Interactions between the compound and CT-DNA were studied with UV-Vis spectra. The UV-Vis

Keywords

Schiff base, Spectroscopy, Anion Sensors, DNA-Binding

References

1. Kajal A, Bala S, Kamboj S, Saini V. Schiff Bases: A versatile pharmacophore. J. Catal. 2013 August; 1-14.
2. Kumar S. Protease inhibiting and other biological activities of Schiff base derivatives. IJRT. 2016; 2(7):439-54.
3. Luo H, Xia Y-F, Sun B-F, Huang L-R, Wang X-H, Lou H-Y, Zhu X-H, Pan W-D, Zhang X-D. Synthesis and evaluation of in vitro antibacterial and antitumor activities of novel N,N-disubstituted Schiff bases. Biochem. Res. Int. 2017 Jun; 2017:6257240.
4. Guo Z, Xing R, Liu S, Zhong Z, Ji X, Wang L, Li P. Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydr. Res. 2007; 342(10):1329–32.
5. Przybylski P, Huczynski A, Pyta K, Brzezinski B, Bartl F. Biological properties of Schiff bases and azo derivatives of phenols. Curr. Org. Chem. 2009; 13(2):124–48.
6. Li H-G, Yang Z-Y, Qin D.D. A new Schiff-base type selective fluorescent chemosensor for Cu2+. Inorg. Chem. Commun. 2009 June; 12 (6):494-7.
7. Zhu W, Yang L, Fang M, Wu Z, Zhang Q, Yin F, Huang Q, Li C. New carbazole-based Schiff base: Colorimetric chemosensor for Fe3+ and fluorescent turn-on chemosensor for Fe3+ and Cr3+. J. Lumin. 2015 February; 158:38-43.
8. Gupta V.K, Singh A.K, Kumawat L.K. Thiazole Schiff base turn-on fluorescent chemosensor for Al3+ ion. Sens. Actuat. B: Chem. 2014 May; 195:98-100.
9. Singh T.S, Paul P.C, Pramanik H.A. Fluorescent chemosensor based on sensitive Schiff base for selective detection of Zn2+. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014; 121:520-6.
10. Xu Y, Aderinto S.O, Wu H, Peng H, Zhang H, Zhang J, Fan X. A highly selective fluorescent chemosensor based on naphthalimide and Schiff base units for Cu2+ detection in aqueous medium. Z. Naturforsch. B. 2016; 72(1):35–41.
11. Hijji Y.M, Barare B, Kennedy A.P, Butcher R. Synthesis and photophysical characterization of a Schiff base as anion sensor. Sens. Actuators B: Chem. 2009 March; 136(2): 297-302.
12. Dalapati S, Jana S, Guchhait N. Anion recognition by simple chromogenic and chromo-fluorogenic salicylidene Schiff base or reduced-Schiff base receptors. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014 Aug; 129:499-508.
13. Mohammadi A, Jabbari J. Simple naked-eye colorimetric chemosensors based on Schiff-base for selective sensing of cyanide and fluoride ions. Can. J. Chem. 2016; 94(7): 631-6.
14. Yıldız M, Demir N, Ünver H, Sahiner N. Synthesis, characterization, and application of a novel water-soluble polyethyleneimine-based Schiff base colorimetric chemosensor formetal cations and biological activity. Sens. Actuators B: Chem. 2017 May; 252: 55–61.
15. Zeyrek C.T, Boyacioğlu B, Yıldız M, Ünver H, Yolal D, Demir N, Elmali A, Tadesse S, Aslan K. Synthesis, characterization, and evaluation of (E)-methyl-2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor. Bioorg. Med. Chem. 2016 Sept.; 24:5592–601.
16. Ünver H, Boyacıoglu B, Zeyrek C.T, Yıldız M, Demir N, Yıldırım N, Karaosmanoğlu O.K, Sivas H, Elmalı A. Synthesis, spectral and quantum chemical studies and use of (E)-3-[(3,5-bis(trifluoromethyl)- phenylimino)methyl]benzene-1,2-diol and its Ni(II) and Cu(II) complexes as an anion sensor, DNA binding, DNA cleavage, anti-microbial, anti-mutagenic and anti-cancer agent. J. Mol. Struct. 2016 June; 1125:162-76.
17. Barare B, Yıldız M, Ünver H, Aslan K. Characterization and use of (E)-2-[(6-methoxybenzo[d]thiazol-2-ylimino)methyl]phenol as an anion sensor and a DNA-binding agent. Tetrahedron Lett. 2016; 57:537–42.
18. Yıldız M, Tan E, Demir N, Yıldırım N, Ünver H, Kiraz A, Mestav B. Synthesis and spectral, antimicrobial, anion sensing, and DNA binding properties of Schiff base podands and their metal Complexes1. Russ. J. Gen. Chem. 2015; 85(9):2149–62.
19. Barare B, Yıldız M, Alpaslan G, Dilek N, Ünver H, Tadesse S, Aslan K. Synthesis, characterization, theoretical calculations, DNA binding and colorimetric anion sensing applications of 1-[(E)-[(6-methoxy-1,3-benzothiazol-2-yl)imino]methyl]naphthalen-2-ol. Sens. Actuat. B: Chem., 2015 March; 215:52–61.
20. Yıldız M, Karpuz Ö, Zeyrek C.T, Boyacioğlu B, Dal H, Demir N, Yıldırım N, Ünver H. Synthesis, biological activity, DNA binding and anion sensors, molecular structure and quantum chemical studies of a novel bidentate Schiff base derived from 3,5-bis(triflouromethyl)aniline and salicylaldehyde. J. Mol. Struct. 2015 April; 1094:148–60.
21. Yeap G.-Y, Ha S.-T, Ishizawa N, Suda K, Boey P.-L, Mahmood W.A.K, Synthesis, crystal structure and spectroscopic study of parasubstituted 2-hydroxy-3-methoxybenzalideneanilines. J. Mol. Struct. 2003; 658:87-99.
22. Martínez-Máñez R, Sancenón F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 2003; 103:4419-76.
23. Uysal UD, Berber H, Ercengiz D. Theoretical investigation on solvent dependent shift and electronic transition properties of certain Schiff bases. JOTCSA, 2018; (4-sp.is.1): 111-30.
24. Kang J, Song E.J, Kim H, Kim Y-H, Kim Y, Kim S-J, Kim C. Specific naked eye sensing of cyanide by chromogenic host: studies on the effect of solvents. Tetrahedron lett. 2013 february; 54:1015-19.
25. Piątek P, Jurczak J, A selective colorimetric anion sensor based on an amide group containing macrocycle. Chem. Commun. 2002; 20:2450-1.
26. Gan C, Zhou L, Zhao Z, Wang H. Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer’s disease. Med. Chem. Res. 2013; 22(9): 4069-74.
27. Piscitelli F, Ballatore C, Smith A. Solid phase synthesis of 2-aminobenzothiazoles. Bioorg. Med. Chem. Lett. 2010; 20(2):644-8.
28. Ali R, Siddiqui N. Biological Aspects of Emerging Benzothiazoles: A Short Review. J. Chem. 2013; 1-12.
29. Vijayalakshmi R, Kanthimathi M, Parthasarathi R, Nair B.U, Interaction of chromium(III) complex of chiral binaphthyl tetradentate ligand with DNA. Bioorg. Med. Chem. 2006 May; 14:3300-6.
30. Li F, Feterl M, Mulyana Y,. Warner J.M, Collins J.G, Keene F.R. In vitro susceptibility and cellular uptake for a new class of antimicrobial agents: Dinuclear ruthenium(II) complexes. J. Antimicrob. Chemother. 2012; 67:2686-95.
31. Marmur J. A procedure for the isolation of deoxyribonucleic acid from micro-organisms. J. Mol. Biol. 1961 April; 3:208-18.
32. Nazır H, Yıldız M, Yılmaz H, Tahir M.N, Ülkü D. Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2-oxo-1-naphthylidenemethylamine. J. Mol. Struct. 2000 June; 524:241-50.