(E)-2-Benzylidenecycloalkanones XII.* Kinetic Measurement of Bovine and Human Serum Albumine Interaction with Selected Chalcones and Their Cyclic Chalcone Analogues by UV Spectrophotometry

Beáta Veliká¹, Vladimíra Tomečková¹, Krisztina Fodor², Ivan Kron¹, Pál Perjési^2*

¹Department of Medical Chemistry, Biochemistry and Clinical Biochemistry, Faculty of Medicine UPJS, Trieda SNP 1, Kosice, Slovakia.
²Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, Hungary.

DOI: 10.4236/sar.2015.31001                

Abstract

UV-VIS spectroscopic investigations of interaction of bovine and human serum albumin with selected chalcones (1) and their cyclic chalcone analogues: (E)-2-(4’-X-benzylidene-1-tetralones (3), benzosuberones (4) with dimethylamino and methoxy substituents and (E)-2-(2’,4’-dimethox- ybenzylidene)-1-indanone (2) were performed in polar respiration medium. Absorption maxima of the tested compounds were investigated in the presence of bovine and human serum albumin at the 0, 10, 30 and 60 minute timepoints of the interaction. The absorbance of all studied compounds in the presence of proteins decreased after one hour of the reaction. Molecule 4a showed the strongest and fastest kinet initial interaction with both albumins.

Keywords

Chalcones, Cyclic Chalcone Analogues, UV Spectra, Kinetic Measurements, Binding Constant Bovine Serum Albumin, Human Serum Albumin

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Huber, I., Zupkó, I., Kovács, I.J., Minorics, R., Gulyás-Fekete, G., Maász, G. and Perjési, P. (2015) Synthesis and Antiproliferative Activity of Cyclic Arylidene Ketones: Direct Comparison of Monobenzylidene and Dibenzylidene Derivatives. Monatshefte für Chemie.
[2]	Rozmer, Z. and Perjési, P. (2014) Naturally Occuring Chalcones and Their Biological Activities. Phytochemistry Reviews. http://dx.doi.org/10.1007/s11101-014-9387-8
[3]	Go, M.L., Wu, X. and Liu, X.L. (2005) Chalcones: An Update on Cytotoxic and Chemoprotective Properties. Current Medicinal Chemistry, 12, 483-499. http://dx.doi.org/10.2174/0929867053363153
[4]	Dimmock, J.R., Kandepu, N.M., Nazarali, A.J., Kowalchuk, T.P., Motaganahalli, N., Quail, J.W., Mykytiuk, P., Audette, G.F., Prasad, L., Perjési, P., Allen, T.M., Santos, C.L., Szydlowski, J., De Chercq, E. and Balzarini, J. (1999) Conformational and Quantitative Structure-Activity Relationship Study of Cytotoxic 2-arylidenebenzocycloalkanones. Journal of Medicinal Chemistry, 42, 1358-1366. http://dx.doi.org/10.1021/jm9806695
[5]	Dimmock, J.R., Zello, G.A., Oloo, E.O., Quail, J.W., Kraatz, H.-B., Perjési, P., Aradi, F., Takács-Novák, K., Allen, T.M., Santos, C.L., Balzarini, J., DeClerq, E. and Stables, J.P. (2002) Correlations between Cytotoxicity and Topography of Some 2-arylidenebenzocycloalkanones Determined by X-Ray Crystallography. Journal of Medicinal Chemistry, 45, 3103-3111. http://dx.doi.org/10.1021/jm010559p
[6]	Perjési, P., Das, U., De Clercq, E., Balzarini, J., Kawase, M., Sakagami, H., Stables, J.P., Loránd, T., Rozmer, Z. and Dimmock, J.R. (2008) Design, Synthesis and Antiproliferative Activity of Some 3-benzylidene-2,3-dihydro-1-benzo- pyran-4-ones Which Display Selective Toxicity for Malignant Cells. European Journal of Medicinal Chemistry, 43, 839-845. http://dx.doi.org/10.1016/j.ejmech.2007.06.017
[7]	Fodor, K., Tomeckova, V., K?szegi, T., Kron, I. and Perjési, P. (2011) (E)-2-Benzylidenebenzocyclanones: Part VI. Solvent Effect on the UV and Fluorescence Properties of Some Chalcones and Their Cyclic Analogues. Interaction of 4-Dimethylaminochalcones with Bovine and Human Serum Albumin: A UV-vis Study. Monatshefte für Chemie— Chemical Monthly, 142, 463-468. http://dx.doi.org/10.1007/s00706-011-0463-0
[8]	Tomecková, V., Perjési, P., Guzy, J., Kusnír, J., Chovanova, Z., Chavkova, Z. and Marekova, M. (2004) Comparison of Effect of Selected Synthetic Chalcone Analogues on Mitochondrial Outer Membrane Determined by Fluorescence Spectroscopy. Journal of Biochemical and Biophysical Methods, 6, 135-141. http://dx.doi.org/10.1016/j.jbbm.2004.04.010
[9]	Tomeckova, V., Poskrobova, M., Stefanisinova, M. and Perjési, P. (2009) Some Fluorescence Properties of Dimethylaminochalcone and Its Novel Cyclic Analogues. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74, 1242-1246. http://dx.doi.org/10.1016/j.saa.2009.09.048
[10]	Pengfei, W. and Shikang, W. (1994) A Study on the Spectroscopy and Photophysical Behaviour of Chalcone Derivatives. Journal of Photochemistry and Photobiology A: Chemistry, 77, 127-131.
[11]	Wang, P.F. and Wu, S.K. (1995) Spectroscopy and Photophysics of Bridged Enone Derivatives: Effect of Molecular Structure and Solvent. Journal of Photochemistry and Photobiology A: Chemistry, 86, 109-113. http://dx.doi.org/10.1016/1010-6030(94)03921-G
[12]	Wang, H., Mei, M., Xie, H.Z., Fang, Y., Zhang, X.H. and Wu, S.K. (2003) A Study on the Fluorescence Quenching of Modified β-Cyclodextrin by Transition Metal Ions in Different Solvents. ARKIVOC, 2, 173-181.
[13]	Fayed, T.A. and Awad, M.K. (2004) Dual Emission of Chalcone-Analogue Dyes Emitting in the Red Region. Chemical Physics, 303, 317-326. http://dx.doi.org/10.1016/j.chemphys.2004.06.023
[14]	Perjési, P., Nusser, T., Tarczay, Gy. and Sohár, P. (1999) E-2-Benzylidenebenzocycloalkanones. Stereostructure and NMR Spectroscopic Investigation. Journal of Molecular Structure, 479, 13-19. http://dx.doi.org/10.1016/S0022-2860(98)00805-9
[15]	Perjési, P., Perjessy, A., Kolehmainen, E., Osz, E., Samalikova, M., Linnanto, J. and Virtanen, E. (2004) E-2-Benzy- lidenebenzocyclanones III. Studies on Transmission of Substituent Effects on IR Carbonyl Stretching Frequencies and 13C NMR Chemical Shifts of E-2-(X-benzylide)-1-Indanones. Comparison of the IR Data of E-2-(X-benzylide)-1-In- danones, -Tetralones and -Benzosuberones. Journal of Molecular Structure, 697, 41-47. http://dx.doi.org/10.1016/j.molstruc.2004.02.006
[16]	Perjési, P., Linnanto, J., Kolehmainen, E., Osz, E. and Virtanen, E. (2005) E-2-Benzylidenebenzocycloalkanones IV. Studies on Transmission of Substituent Effects on 13C NMR Chemical Shifts of E-2-(X-benzylidene)-1-tetralones, and -benzosuberones. Comparison with the 13C NMR Data of Chalcones and E-2-(X-benzylidene)-1-Indanones. Journal of Molecular Structure, 740, 81-89. http://dx.doi.org/10.1016/j.molstruc.2004.10.013
[17]	Wolfbeis, O.S., Begum, M. and Geiger, H. (1984) Fluorescence Properties of Hydroxyl- and Methoxyflavones and the Effect of Shift Reagents. Zeitschrift für Naturforschung, 39, 231-237.
[18]	Asiri, A.M. (2003) Synthesis and Absorption Spectral Properties of Bis-Methine Dyes Exemplified by 2,5-Bis-Aryli- dene-1-Dicyanomethylene-Cyclopentanes. Bulletin of the Korean Chemical Society, 24, 426-430. http://dx.doi.org/10.5012/bkcs.2003.24.4.426
[19]	Zhang, C.H., Chen, Z.B. and Jiang, Y.B. (2004) Intramolecular Charge Transfer Dual Fluorescence of p-dimethylami- nobenzoates. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 60, 2729-2732. http://dx.doi.org/10.1016/j.saa.2004.01.011
[20]	Reichardt, C. (1994) Solvatochromic Dyes as Solvent Polarity Indicators. Chemical Reviews, 94, 2319-2358. http://dx.doi.org/10.1021/cr00032a005
[21]	Wang, H., Borguet, E. and Eisenthal, K.B. (1997) Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy. Journal of Physical Chemistry A, 101, 713-718. http://dx.doi.org/10.1021/jp962074w
[22]	Marder, S.R., Cheng, L.T., Tiemann, B.G., Friedli, A.C., BlanchardDesce, M., Perry, J.W. and Skindhoj, J. (1994) Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity. Science, 263, 511-514. http://dx.doi.org/10.1126/science.263.5146.511
[23]	Domagalska, B.W., Wilk, K.A. and Zielinski, R. (2006) Spectroscopic and Electrochemical Properties of New Amphiphilic Donor-Acceptor Conjugated Polyenes. Journal of Photochemistry and Photobiology A: Chemistry, 184, 193- 203. http://dx.doi.org/10.1016/j.jphotochem.2006.04.015