CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism

Authorized Users Only
2015
Authors
Senćanski, Milan
Došen-Mićović, Ljiljana
Šukalović, Vladimir
Kostić Rajačić, Slađana
Article (Published version)
Metadata
Show full item record
Abstract
Contacts between aromatic rings and sulfur-containing amino acids are frequent in proteins. However, little is known about the nature of their interactions particularly if substituents are present on aromatic ring. In this paper, DFT quantum chemical calculations were used to study substituted benzenes in complex with hydrogen sulfide (H2S), methanethiol (CH3SH), and (Methylsulfanyl)methane (CH3SCH3). It was found that SH(...)a interaction is more stabilizing than the S(...)a interaction in the case of benzene, but this is changed with increasing electronegativity of the substituent on benzene ring. Although the change of energy of SH...pi and S-...pi interaction follows the conventional model of substituent effect, where S-...pi interactions are maximized and SH...pi interactions are diminished with electron-withdrawing substituent on benzene as a result of changes in the aryl it-system, it was found that it is mainly a consequence of direct electrostatic interaction between substitue...nt and the sulfur-containing molecule. We also investigated the model system of Cys(...)Trp interaction, adjacent to a cluster of aromatic amino acids, in proteins, using explicit membrane molecular dynamics simulations results of D-3 dopamine receptor crystal structure as starting point. It was found that fluorination in aromatic cluster enhances the Cys(...)Trp interaction. The effect is maximized when transferred through the rest of aromatic system suggesting possible explanation for frequent contacts between sulfur-containing and aromatic amino acids in proteins and their effects on protein folding and stabilization.

Keywords:
Sulfur-pi interactions / DFT calculations / Molecular dynamics / Dopamine D-2 receptor
Source:
Structural Chemistry, 2015, 26, 4, 1139-1149
Publisher:
  • Springer/Plenum Publishers, New York
Projects:
  • Structure-activity relationship of newly synthesized biological active compound (RS-172032)

DOI: 10.1007/s11224-015-0574-z

ISSN: 1040-0400

WoS: 000358063000022

Scopus: 2-s2.0-84937817235
[ Google Scholar ]
9
9
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1617
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB