For citation:
Pankratov A. N., Tsivileva O. M., Drevko B. I., Nikitina V. E. Quantum Chemical Study and QSAR Properties of 3-Seleno- pentanediones-1,5 Aromatic Derivatives: Prerequisites for Inter action with the Carbohydrate-Binding Proteins. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2010, vol. 10, iss. 1, pp. 7-13. DOI: 10.18500/1816-9775-2010-10-1-7-13
Quantum Chemical Study and QSAR Properties of 3-Seleno- pentanediones-1,5 Aromatic Derivatives: Prerequisites for Inter action with the Carbohydrate-Binding Proteins
The role of spatial and electronic structure, hydrophobic properties and concentration of organoselenium compounds on their interaction with fungal metabolites - carbohydrate-binding proteins, extracellular lectins of Lentinula edodes (shiitake mushroom) has been consi dered. By the hybrid density functional theory method at the B3LYP/6-31G(d,p) theory level, spatial and electronic structure of the 1,5-di(4-R-phenyl)-3-selenopentanediones-1,5 molecules has been studied. By means of the QSAR properties evaluation by the atomic- bonding-additive schemes, the distinct hydrophobicity of these com pounds has been demonstrated. The theoretical characteristics thus obtained have been used for interpreting the experimental data on the lectin activity enhancement in the presence of 1,5-di(4-R-phenyi)- 3-selenopentanediones-1,5, as well as on the greatest efficiency of ethoxy derivative.
|
1. |
Whanger P.D. Selenocompounds in Plants and Animals and Their Biological Significance // J. Amer. Coll. Nutr. 2002, Vol.21, №3.P.223-232. |
|
2. |
Mikiashvili N., Elisashvili V., Wasset- S.P., Nevo E. Comparative Study of Lectin Activity of Higher Basidiomycetes // Int. J. Med. Mushrooms. 2006. Vol.8, Iss.l. P.31-38. EDN: MHAKKP |
|
3. |
Яуцик М.Д., Панамок Е.К, Луцик А.Д. Лектины. Львов, 1981. 156 с. |
|
4. |
Цивилева О.М., Никитина В.Е., Лощинина Е.А. Выделение и характеристика внеклеточных лектинов Lentinus edodes (Berk.) Sing // Биохимия. 2008. T.73, №10. С.1438-1446. EDN: JUUYOR |
|
5. |
Цивилева О.М, Никитина В. Е., Панкратов А.Я, Древко Б.И., Лощинина Е.А., Гарыбова Л.В. Влияние селенсо-держащего препарата ДАФС-25 на рост и лектиновую активность Lentinus edodes i/ Биотехнология. 2005. №2. С.56-62. EDN: HVTSAT |
|
6. |
Кон В. Электронная структура вещества - волновые функции и функционалы плотности // УФН. 2002, Т. 172, №3. С.336-348. |
|
7. |
Becke A.D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior // Physical Review A. 1988. Vol.38, №6. P.3098-3100. EDN: SMQBQL |
|
8. |
Becke А.D. Density-Functional Thermochemistry. III. The Role of Exact Exchange // J. Chem. Phys. 1993. Vol.98, №7. P.5648-5652. EDN: SGUIWZ |
|
9. |
Lee C, Yang W, Parr R.G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density // Physical Review B. 1988. Vol.37, №2. P.785-789. |
|
10. |
Ditchfield R., Hehre WJ., Popte J.A. A Self-Consistent Molecular-Orbital Methods. ГХ. An Extended Gaussian-Type Basis for Molecular-Orbital Studies of Organic Molecules // J. Chem. Phys. 1971. Vol.54, №2. P.724-728. |
|
11. |
Blessing H., Kraus S., Heindl P., Bal W., Hartwig A. Interaction of selenium compounds with zinc finger proteins involved in DNA repair // Eur. J. Biochem. 2004. Vol.271, №15. P.3190-3199. EDN: MGJYRL |
|
12. |
Jacob C, Maret W., Vallee B.L. Selenium redox biochemistry of zinc-sulfur coordination sites in proteins and enzymes // Proc. Natl. Acad. Sci. USA. 1999. Vol.96, №5. P.1910-1914. |
|
13. |
Turan В., Eliss H., Desilets M. Oxidants increase the intracellular free Zn2 concentration in rabbit ventricular myocytes // Amer. J. Physiol. 1997. Vol.272, №5 (Pt.2). P.2095-2106. |
|
14. |
Ganther H.E. Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thiore-doxin reductase // Carcinogenesis. 1999. Vol.20, №9. P.1657-1666. EDN: IMVBLV |
|
15. |
Jacob C, Giles G.I., Giles N.M., Sies H. Sulfur and selenium: the role of oxidation state in protein structure and function // Angew. Chem. Int. Ed. Engl. 2003. Vol.42, №39. P.4742-4758. |
|
16. |
Лахтин В.М. Биотехнология лектинов // Биотехнология. 1989. T.5, №6. C.676-691. EDN: IEXDQO |
|
17. |
Лахтин В.М. Молекулярная организация лектинов // Молекулярная биология. 1994. Т.28, вып.2. С.245-273. EDN: NFBRGS |
|
18. |
Elgavish S., Shaanan В. Eectin-Carbohydrate Interactions: Different Folds, Common Recognition Principles // Trends Biochem. Sci. 1997. Vol.22, №12. P.462-467. EDN: AKOHSZ |
|
19. |
Hasel W., Hendrickson Т.Е., Still W.C. A Rapid Approximation to the Solvent-Accessible Surface Areas of Atoms // Tetrahedron Computer Methodology. 1988. Vol.1, №2. P.103-116. |
|
20. |
Still W.C., Tempczyk A., Haw ley R.C., Hendrickson Th, Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics // J. Amer. Chem. Soc. 1990. Vol.112, №16. P.6127-6129. |
|
21. |
Bodor N., Gabanyi Z., Wong Chu-Kuok. A New Method for the Estimation of Partition Coefficient // J. Amer. Chem. Soc. 1989. Vol.111, №11. P.3783-3786. |
|
22. |
Gavezotti A. The Calculation of Molecular Volumes and the Use of Volume Analysis in the Investigation of Structured Media and of Solid-State Organic Reactivity // J. Amer. Chem. Soc. 1983. Vol.105, №16. P.5220-5225. |
|
23. |
Ghose A.K., Crippen G.M. Atomic Physicochemical Parameters for Three-Dimensional Structure-Directed Quantitative Structure - Activity Relationships. I. Partition Coefficients As a Measure of Hydrophobicity // J. Comput. Chem. 1986. Vol.7,№4.P.565-577. |
|
24. |
Ghose A.K., Crippen G.M. Atomic Physicochemical Parameters for Three-Dimensional-Structure-Directed Quantitative Structure - Activity Relationships. 2. Modelling Disperse and Hydrophobic Interactions // J. Chem. Inf. and Comput. Sci. 1987. Vol.27, №1.P.21-35. |
|
25. |
Viswanadhan V.N., Ghose A.K., Revankar G.N., Robins R.K. Atomic Physicochemical Parameters for Three Dimensional Structure Directed Quantitative Structure - Activity Relationships. 4. Additional Parameters for Hydrophobic and Dispersive Interactions and Their Application for an Automated Superposition of Certain Naturally Occurring Nucleoside Antibiotics // J. Chem. Inf. and Comput. Sci. 1989. Vol.29, №3. P.163-172. |
|
26. |
Miller K.J. Additivity Methods in Molecular Polarisability //J. Amer. Chem. Soc. 1990. Vol.112, №23. P.8533-8542. |
|
27. |
Ghose A.K., Pritchett A., Crippen G.M. Atomic Physico-chemical Parameters for Three Dimensional Structure Directed Quantitative Structure - Activity Relationships III. Modelling Hydrophobic Interactions // J. Comput. Chem. 1988. Vol.99, №l.P.80-90. |