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Pregled bibliografske jedinice broj: 939296

Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs


Oanca, Gabriel; Stare, Jernej; Vianello, Robert; Mavri, Janez
Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs // European journal of pharmacology, 817 (2017), 46-50 doi:10.1016/j.ejphar.2017.05.061 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 939296 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs

Autori
Oanca, Gabriel ; Stare, Jernej ; Vianello, Robert ; Mavri, Janez

Izvornik
European journal of pharmacology (0014-2999) 817 (2017); 46-50

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Monoamine oxidase ; Molecular simulation ; QM/MM methodology ; Empirical valence bond ; Neurotransmitters ; Phenylethylamine

Sažetak
Phenylethylamine (PEA) is an endogenous amphetamine and its levels are increased by physical activity. As other biogenic monoamines, it is decomposed by monoamine oxidase (MAO) enzymes. The chemical mechanism of MAO, and flavoenzymes in general, is a subject of heated debate. We have previously shown that the rate-limiting step of MAO catalysis involves a hydride transfer from the substrate methylene group vicinal to the amino group to the N5 atom of the lumiflavin co-factor moiety. By using multiscale simulation on the Empirical Valence Bond (EVB) level, we studied the chemical reactivity of the monoamine oxidase B catalyzed decomposition of PEA and its two derivatives: p-chloro-β-methylphenylamine (p-CMP) and p-methoxy-β-methylphenethylamine (p-MMP). We calculated activation free energies of 17.1 kcal/mol (PEA), 18.4 kcal/mol (p-MMP) and 20.0 kcal/mol (p-CMP), which are in excellent agreement with the experimental values of 16.7 kcal/mol for PEA and 18.3 kcal/mol for p-MMP, while the experimental value for p-CMP is not available. This gives strong support to the validity of our hydride transfer mechanism for both MAO A and B isoforms. The results are discussed in the context of the interplay between MAO point mutations and neuropsychiatric disorders.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
EK-FP7-334493 - Korištenje računalnih tehnika istraživanja biogenih amina u mozgu za liječenje neuroloških bolesti (COMPBAND) (Vianello, Robert, EK ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Robert Vianello (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com

Citiraj ovu publikaciju:

Oanca, Gabriel; Stare, Jernej; Vianello, Robert; Mavri, Janez
Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs // European journal of pharmacology, 817 (2017), 46-50 doi:10.1016/j.ejphar.2017.05.061 (međunarodna recenzija, članak, znanstveni)
Oanca, G., Stare, J., Vianello, R. & Mavri, J. (2017) Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs. European journal of pharmacology, 817, 46-50 doi:10.1016/j.ejphar.2017.05.061.
@article{article, author = {Oanca, Gabriel and Stare, Jernej and Vianello, Robert and Mavri, Janez}, year = {2017}, pages = {46-50}, DOI = {10.1016/j.ejphar.2017.05.061}, keywords = {Monoamine oxidase, Molecular simulation, QM/MM methodology, Empirical valence bond, Neurotransmitters, Phenylethylamine}, journal = {European journal of pharmacology}, doi = {10.1016/j.ejphar.2017.05.061}, volume = {817}, issn = {0014-2999}, title = {Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs}, keyword = {Monoamine oxidase, Molecular simulation, QM/MM methodology, Empirical valence bond, Neurotransmitters, Phenylethylamine} }
@article{article, author = {Oanca, Gabriel and Stare, Jernej and Vianello, Robert and Mavri, Janez}, year = {2017}, pages = {46-50}, DOI = {10.1016/j.ejphar.2017.05.061}, keywords = {Monoamine oxidase, Molecular simulation, QM/MM methodology, Empirical valence bond, Neurotransmitters, Phenylethylamine}, journal = {European journal of pharmacology}, doi = {10.1016/j.ejphar.2017.05.061}, volume = {817}, issn = {0014-2999}, title = {Multiscale simulation of monoamine oxidase catalyzed decomposition of phenylethylamine analogs}, keyword = {Monoamine oxidase, Molecular simulation, QM/MM methodology, Empirical valence bond, Neurotransmitters, Phenylethylamine} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


Citati:





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