Synthesis, crystal structure, DFT calculation and DNA binding studies of new water-soluble derivatives of dppz
| Autor: | Reza Kia, Mohammad Aminzadeh, Abbas Eslami, Roghayeh Aleeshah |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Steric effects
010405 organic chemistry Organic Chemistry Intercalation (chemistry) Phenazine Crystal structure 010402 general chemistry 01 natural sciences Binding constant 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Crystallography DNA Intercalation chemistry Spectroscopy DNA Methyl group |
| Zdroj: | Journal of Molecular Structure. 1145:141-151 |
| ISSN: | 0022-2860 |
| Popis: | Diquaternarization of dipyrido-[2,3-a:2′,3′-c]-phenazine,(dppz) and its analogous dipyrido-[2,3-a:2′,3′-c]-dimethylphenazine,(dppx) using 1,3-dibromopropane afford new water-soluble derivatives of phenazine, propylene-bipyridyldiylium-phenazine (1) and propylene-bipyridyldiylium-dimethylphenazine (2). The compounds have been characterized by means of FT-IR, NMR, elemental analysis and conductometric measurements and their structure were determined by X-ray crystallography. The experimental studies on the compounds have been accompanied computationally by Density Functional Theory (DFT) calculations. The DNA binding properties of both compounds to calf thymus DNA (ctDNA) were investigated by UV–Vis absorption and emission methods. The expanded UV–Vis spectral data matrix was analyzed by multivariate curve resolution-alternating least squares (MCR-ALS) technique to obtain the concentration profile and pure spectra of all reaction species which existed in the interaction procedure. Multivariate curve resolution may help us to give a better understanding of the 1(Cl)2–ctDNA and 2(Cl)2–ctDNA interaction mechanism. The results suggest that both compounds bind tightly to DNA through intercalation mechanism and the DNA binding affinity of 2 is slightly lower than that of 1 due to steric hindrance of the methyl group. Also, thermal denaturation studies reveal that these compounds show strong affinity for binding with calf thymus DNA. The thermodynamic parameters of the DNA binding process were obtained from the temperature dependence of the binding constants and the results showed that binding of both compounds to DNA is an enthalpically driven process that is in agreement with proposed DNA intercalation capability of these compounds. |
| Databáze: | OpenAIRE |
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