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Computational Studies on Effects of MDMA as an Anticancer Drug on DNA
Author(s) -
Riahi Siavash,
Eynollahi Solmaz,
Ganjali Mohammad R.
Publication year - 2010
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2010.01027.x
Subject(s) - thymine , guanine , cytosine , stacking , chemistry , dna , intercalation (chemistry) , mdma , base pair , nucleobase , nucleic acid , stereochemistry , computational chemistry , nucleotide , biochemistry , biology , pharmacology , organic chemistry , gene
This research is designed to further understand the effects of the novel drug MDMA on biologic receptor of DNA. The ultimate goal is to design drugs that have higher affinity with DNA. Understanding the physicochemical properties of the drug as well as the mechanism by which it interacts with DNA should ultimately enable the rational design of novel anticancer or antiviral drugs. Molecular modeling on the complex formed between MDMA and DNA presented this complex to be fully capable of participating in the formation of a stable intercalation site. Furthermore, the molecular geometries of MDMA and DNA bases (Adenine, Guanine, Cytosine, and Thymine) were optimized with the aid of the B3LYP/6‐31G* method. The properties of the isolated intercalator and its stacking interactions with adenine···thymine (AT) and guanine···cytosine (GC) nucleic acid base pairs were studied with the DFTB method. DFTB method is an approximate version of the DFT method that was extended to cover the London dispersion energy. The B3LYP/6‐31G* stabilization energies of the intercalator···base pair complexes were found to be −9.40 and −12.57 kcal/mol for AT···MDMA and GC···MDMA, respectively. Results from comparison of the DFTB method and HF method conclude close results and support each other.