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Yeni bir imin bileşiğinin yapısal karakterizasyonu ve DNA bağlanma özellikleri

Year 2020, Volume: 41 Issue: 2, 407 - 412, 25.06.2020

Muhammet Köse , Ozge Gungör Julide Nacaroglu Ballı Hilal Kırpık

https://doi.org/10.17776/csj.594938

Abstract

Bu çalışmada, o-vanilin ve 4-izopropilanilin
reaksiyonundan yeni bir imin bileşiği (M) sentezlenmiştir. Bileşiğin yapısı,
spektroskopik ve analitik yöntemlerle karakterize edilmiştir. Bileşiğin tekli
kristalleri elde edilerek katı hal yapısı X-ışını kırınım çalışması ile
karakterize edilmiştir. Bileşiğin UV-Vis absorpsiyon ve emisyon özellikleri
farklı çözücülerde çalışılmıştır. Ayrıca, bileşiğin DNA bağlama kabiliyeti
araştırılmış ve standart DNA bağlayıcı ajanlarla karşılaştırılmıştır. Bileşik,
spermin ve etidyum bromüre yakın bağlanma sabiti (4 x 105 M-1) sahip olduğu bulunmuştur.

References

  • [1] Ceyhan G, Köse M., Tümer M. and Demirtaş I. Anticancer, photoluminescence and electrochemical properties of structurally characterized two imine derivatives. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 149 (2015) 731-743.
  • [2] Al Zoubi W. and Ko, Y. G. Schiff base complexes and their versatile applications as catalysts in oxidation of organic compounds: part I. Applied Organometallic Chemistry, 31 (2017) 3574.
  • [3] Al Zoubi W., Kandil F. and Chebani, M. K. Solvent extraction of chromium and copper using Schiff base derived from terephthaldialdehyde and 5-amino-2-methoxy-phenol. Arabian Journal of Chemistry, 9 (2016) 526-531.
  • [4] Kandil F., Al Zoubi W. and Chebani M. K., The synthesis and characterization of new Schiff bases and investigating them in solvent extraction of chromium and copper. Separation Science and Technology, 47 (2012) 754-1761.
  • [5] Köse M., Ceyhan G., Tümer M., Demirtaş I., Gönül I. and McKee V. Monodentate Schiff base ligands: Their structural characterization, photoluminescence, anticancer, electrochemical and sensor properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 137 (2015) 477-485.
  • [6] Oliveira-Brett A. M., Diculescu V. and Piedade J. A. P. Electrochemical oxidation mechanism of guanine and adenine using a glassy carbon microelectrode. Bioelectrochemistry, 55 (2002) 61-62.
  • [7] Kuetche V. An initio bubble-driven denaturation of double-stranded DNA: selfmechanical theory. Journal of Theoretical Biology, 401 (2016) 15-29.
  • [8] Sammriski E., Schwartz D. and Pablo J., A mesoscale model of DNA and its renaturation. Biophysical Journal, 96 (2009) 1675-1690.
  • [9] Sheldrick G.M., A short history of SHELX, Acta Crystallogr. Sect. A Found. Crystallogr, 64 (2007) 112-122.
  • [10] Sheldrick G.M., Crystal structure refinement with SHELXL, Acta Crystallogr. Sect. C: Struct. Chem., 71 (2015) 3-8.
  • [11] Gözel A., Kose M., Karakaş D., Atabey H., McKee V. and Kurtoglu M., Spectral, structural and quantum chemical computational and dissociation constant studies of a novel azo-enamine tautomer. Journal of Molecular Structure, 1074 (2014) 449-456.
  • [12] Strekowski L., Harden D. B., Wydra R. L., Stewart K. D. and Wilson W. D. Molecular basis for potentiation of bleomycin‐mediated degradation of DNA by polyamines. Experimental and molecular mechanical studies. Journal of Molecular Recognition, 2 (1989) 158-166.
  • [13] Chaires J. B., A thermodynamic signature for drug–DNA binding mode. Archives of biochemistry and biophysics, 453 (2006) 26-31.
  • [14] Strekowski L. and Wilson B. Noncovalent interactions with DNA: an overview. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 623 (2007) 3-13.

Structural characterization and DNA binding properties of a new imine compound

Year 2020, Volume: 41 Issue: 2, 407 - 412, 25.06.2020

Muhammet Köse , Ozge Gungör Julide Nacaroglu Ballı Hilal Kırpık

https://doi.org/10.17776/csj.594938

Abstract

In this study, a new imine compound (M) was prepared from the reaction of o-vanillin and 4-isopropylaniline. The structure of the compound was characterized by the spectroscopic and analytical methods. Single crystals of the compound were grown and solid-state structure of the compound was further characterized by X-ray diffraction study. The UV-Vis absorption and emission properties of the compound were studied in different solvents. Moreover, DNA binding ability of the compound was investigated and compared with the standard DNA binding agents. The compound showed similar binding constant (4 x 105 M-1) to those spermine and ethidiumbromide.

Keywords

Imine Absorption Emission X-ray DNA binding

References

  • [1] Ceyhan G, Köse M., Tümer M. and Demirtaş I. Anticancer, photoluminescence and electrochemical properties of structurally characterized two imine derivatives. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 149 (2015) 731-743.
  • [2] Al Zoubi W. and Ko, Y. G. Schiff base complexes and their versatile applications as catalysts in oxidation of organic compounds: part I. Applied Organometallic Chemistry, 31 (2017) 3574.
  • [3] Al Zoubi W., Kandil F. and Chebani, M. K. Solvent extraction of chromium and copper using Schiff base derived from terephthaldialdehyde and 5-amino-2-methoxy-phenol. Arabian Journal of Chemistry, 9 (2016) 526-531.
  • [4] Kandil F., Al Zoubi W. and Chebani M. K., The synthesis and characterization of new Schiff bases and investigating them in solvent extraction of chromium and copper. Separation Science and Technology, 47 (2012) 754-1761.
  • [5] Köse M., Ceyhan G., Tümer M., Demirtaş I., Gönül I. and McKee V. Monodentate Schiff base ligands: Their structural characterization, photoluminescence, anticancer, electrochemical and sensor properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 137 (2015) 477-485.
  • [6] Oliveira-Brett A. M., Diculescu V. and Piedade J. A. P. Electrochemical oxidation mechanism of guanine and adenine using a glassy carbon microelectrode. Bioelectrochemistry, 55 (2002) 61-62.
  • [7] Kuetche V. An initio bubble-driven denaturation of double-stranded DNA: selfmechanical theory. Journal of Theoretical Biology, 401 (2016) 15-29.
  • [8] Sammriski E., Schwartz D. and Pablo J., A mesoscale model of DNA and its renaturation. Biophysical Journal, 96 (2009) 1675-1690.
  • [9] Sheldrick G.M., A short history of SHELX, Acta Crystallogr. Sect. A Found. Crystallogr, 64 (2007) 112-122.
  • [10] Sheldrick G.M., Crystal structure refinement with SHELXL, Acta Crystallogr. Sect. C: Struct. Chem., 71 (2015) 3-8.
  • [11] Gözel A., Kose M., Karakaş D., Atabey H., McKee V. and Kurtoglu M., Spectral, structural and quantum chemical computational and dissociation constant studies of a novel azo-enamine tautomer. Journal of Molecular Structure, 1074 (2014) 449-456.
  • [12] Strekowski L., Harden D. B., Wydra R. L., Stewart K. D. and Wilson W. D. Molecular basis for potentiation of bleomycin‐mediated degradation of DNA by polyamines. Experimental and molecular mechanical studies. Journal of Molecular Recognition, 2 (1989) 158-166.
  • [13] Chaires J. B., A thermodynamic signature for drug–DNA binding mode. Archives of biochemistry and biophysics, 453 (2006) 26-31.
  • [14] Strekowski L. and Wilson B. Noncovalent interactions with DNA: an overview. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 623 (2007) 3-13.
There are 14 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Muhammet Köse 0000-0002-4597-0858

Ozge Gungör 0000-0003-3529-2704

Julide Nacaroglu Ballı 0000-0001-9736-7981

Hilal Kırpık 0000-0001-9097-6485

Publication Date June 25, 2020
Submission Date July 22, 2019
Acceptance Date April 17, 2020
Published in Issue Year 2020Volume: 41 Issue: 2

Cite

APA Köse, M., Gungör, O., Nacaroglu Ballı, J., Kırpık, H. (2020). Structural characterization and DNA binding properties of a new imine compound. Cumhuriyet Science Journal, 41(2), 407-412. https://doi.org/10.17776/csj.594938