Molecular modeling study of intercalation complexes of tricyclic carboxamides with d(CCGGCGCCGG)2 and d(CGCGAATTCGCG)2

dc.contributor.author	Βαρβαρέσου, Αθανασία	el
dc.contributor.author	Ιακώβου, Κρίτων	el
dc.date.accessioned	2015-04-28T14:27:07Z
dc.date.available	2015-04-28T14:27:07Z
dc.date.issued	2015-04-28
dc.identifier.uri	http://hdl.handle.net/11400/9161
dc.rights	Αναφορά Δημιουργού-Μη Εμπορική Χρήση-Όχι Παράγωγα Έργα 3.0 Ηνωμένες Πολιτείες	*
dc.rights.uri	http://creativecommons.org/licenses/by-nc-nd/3.0/us/	*
dc.source	http://link.springer.com	el
dc.subject	Καλλυντικά
dc.subject	Χημικά σκευάσματα
dc.subject	Δερματικές αντιδράσεις
dc.subject	Cosmetics
dc.subject	Chemical preparations
dc.subject	Skin reactions
dc.title	Molecular modeling study of intercalation complexes of tricyclic carboxamides with d(CCGGCGCCGG)2 and d(CGCGAATTCGCG)2	en
heal.type	journalArticle
heal.classification	Aesthetics
heal.classification	Chemistry
heal.classification	Αισθητική
heal.classification	Χημεία
heal.classificationURI	http://id.loc.gov/authorities/subjects/sh85001441
heal.classificationURI	http://id.loc.gov/authorities/subjects/sh85022986
heal.classificationURI	N/A-Αισθητική
heal.classificationURI	N/A-Χημεία
heal.identifier.secondary	10.1007/s00894-010-0891-5
heal.language	en
heal.access	campus
heal.recordProvider	Τεχνολογικό Εκπαιδευτικό Ίδρυμα Αθηνών. Σχολή Επαγγελμάτων Υγείας και Πρόνοιας. Τμήμα Αισθητικής και Κοσμητολογίας	el
heal.publicationDate	2011-08
heal.bibliographicCitation	Varvaresou, A. and Iakovou, K. (2010) Molecular modeling study of intercalation complexes of tricyclic carboxamides with d(CCGGCGCCGG)2 and d(CGCGAATTCGCG)2. "Journal of Molecular Modeling", 17 (8), p.2041-2050	en
heal.abstract	Tricyclic dyes with different mesoatoms such as xanthenes (fluorescein, eosin) anthracenes and acridines (proflavine) approved by the Food and Drug Administration (FDA) for use in foods, pharmaceuticals and cosmetic preparations interact with DNA, and some of them do so through intercalation. Hyperchem 7.5, Spartan 04, Yasara 10.5.14 program packages and molecular modeling, molecular mechanics and dynamics techniques with the oligonucleotides d(CCGGCGCCGG)2 and d(CGCGAATTCGCG)2 were utilized in order to examine the mode of binding to DNA of a range of tricyclic carboxamides bearing N,N-dimethylaminoethyl side chain, i.e., 9-amino-DACA, anthracene, acridine-1-carboxamide, acridine-4-carboxamide (DACA), azacridine, phenazine, pyridoquinoxaline, oxopyridoquinoxaline, phenoxazine and xanthenone or N,N-dimethylaminobutyl moiety, i.e., phenazine and acridine. The bicyclic quinoline-8-carboxamide was also examined for comparison reasons. On the basis of our data, prerequisite for the interaction between protonated N,N-dimethylaminoethyl moiety and guanine is the formation of only one internal hydrogen bond between carboxamide and peri NH + in the case of 9-amino-DACA or peri N in the cases of DACA, azacridine, phenazine and pyridoquinoxaline. The presence of an additional internal hydrogen bond between oxygen carboxamide and protonated N,N-dimethylamino group in the cases of tricyclic systems bearing peri NH (phenoxazine) or O (xanthenone) group, prevents the interaction between side chain and guanine. Also, the formation of one internal hydrogen bond between oxygen carboxamide and protonated N,N-dimethylamino group inhibits the interaction between side chain and guanine in the case of acridine-1-carboxamide. Our findings are in accordance with previously reported results obtained from the kinetic studies of the binding of acridine and related tricyclic carboxamides to DNA.	en
heal.publisher	Springer	el
heal.journalName	Journal of Molecular Modeling	en
heal.journalType	peer-reviewed
heal.fullTextAvailability	false
heal.dateCreated	2010-12-14