Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism
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2015
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Sulfur-pi interactions / DFT calculations / Molecular dynamics / Dopamine D-2 receptorIzvor:
Structural Chemistry, 2015, 26, 4, 1139-1149Izdavač:
- Springer/Plenum Publishers, New York
Finansiranje / projekti:
- Proučavanje odnosa strukture i aktivnosti novosintetisanih biološki aktivnih supstanci (RS-MESTD-Basic Research (BR or ON)-172032)
DOI: 10.1007/s11224-015-0574-z
ISSN: 1040-0400
WoS: 000358063000022
Scopus: 2-s2.0-84937817235
Institucija/grupa
IHTMTY - JOUR AU - Senćanski, Milan AU - Došen-Mićović, Ljiljana AU - Šukalović, Vladimir AU - Kostić Rajačić, Slađana PY - 2015 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1617 AB - 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 substituent 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. PB - Springer/Plenum Publishers, New York T2 - Structural Chemistry T1 - Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism VL - 26 IS - 4 SP - 1139 EP - 1149 DO - 10.1007/s11224-015-0574-z ER -
@article{ author = "Senćanski, Milan and Došen-Mićović, Ljiljana and Šukalović, Vladimir and Kostić Rajačić, Slađana", year = "2015", 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 substituent 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.", publisher = "Springer/Plenum Publishers, New York", journal = "Structural Chemistry", title = "Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism", volume = "26", number = "4", pages = "1139-1149", doi = "10.1007/s11224-015-0574-z" }
Senćanski, M., Došen-Mićović, L., Šukalović, V.,& Kostić Rajačić, S.. (2015). Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism. in Structural Chemistry Springer/Plenum Publishers, New York., 26(4), 1139-1149. https://doi.org/10.1007/s11224-015-0574-z
Senćanski M, Došen-Mićović L, Šukalović V, Kostić Rajačić S. Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism. in Structural Chemistry. 2015;26(4):1139-1149. doi:10.1007/s11224-015-0574-z .
Senćanski, Milan, Došen-Mićović, Ljiljana, Šukalović, Vladimir, Kostić Rajačić, Slađana, "Theoretical insight into sulfur aromatic interactions with extension to D-2 receptor activation mechanism" in Structural Chemistry, 26, no. 4 (2015):1139-1149, https://doi.org/10.1007/s11224-015-0574-z . .