Pretražite po imenu i prezimenu autora, mentora, urednika, prevoditelja

Napredna pretraga

Pregled bibliografske jedinice broj: 1070822

Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases


Maraković, Nikola; Knežević, Anamarija; Rončević, Igor; Brazzolotto, Xavier; Kovarik, Zrinka; Šinko, Goran
Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases // Biochemical Journal, 477 (2020), 2771-2790 doi:10.1042/bcj20200192 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1070822 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases

Autori
Maraković, Nikola ; Knežević, Anamarija ; Rončević, Igor ; Brazzolotto, Xavier ; Kovarik, Zrinka ; Šinko, Goran

Izvornik
Biochemical Journal (0264-6021) 477 (2020); 2771-2790

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

Ključne riječi
cholinesterase ; hydroxyiminoacetamide ; reactivation ; stereoselectivity ; PM7R6 method

Sažetak
The enantiomers of racemic 2-hydroxyimino-N-(azidophenylpropyl)acetamide-derived triplebinding oxime reactivators were separated, and tested for inhibition and reactivation of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibited with tabun (GA), cyclosarin (GF), sarin (GB), and VX. Both enzymes showed the greatest affinity toward the methylimidazole derivative (III) of 2-hydroxyimino-N-(azidophenylpropyl)acetamide (I). The crystal structure was determined for the complex of oxime III within human BChE, confirming that all three binding groups interacted with active site residues. In the case of BChE inhibited by GF, oximes I (kr = 207 M-1 min-1) and III (kr = 213 M-1 min-1) showed better reactivation efficiency than the reference oxime 2-PAM. Finally, the key mechanistic steps in the reactivation of GF-inhibited BChE with oxime III were modelled using the PM7R6 method, stressing the importance of proton transfer from Nε of His438 to Oγ of Ser203 for achieving successful reactivation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Javno zdravstvo i zdravstvena zaštita, Farmacija



POVEZANOST RADA


Projekti:
HRZZ-IP-2013-11-4307 - Dizajn, sinteza i evaluacija novih protuotrova kod trovanja živčanim bojnim otrovima i pesticidima (CHOLINESTERASE) (Kovarik, Zrinka, HRZZ - 2013-11) ( POIROT)
HRZZ-IP-2018-01-7683 - Analiza interakcija butirilkolinesteraze s novim inhibitorima i reaktivatorima (AnalyseBChE) (Kovarik, Zrinka, HRZZ - 2018-01) ( POIROT)

Ustanove:
Institut za medicinska istraživanja i medicinu rada, Zagreb,
Institut "Ruđer Bošković", Zagreb

Poveznice na cjeloviti tekst rada:

doi doi.org portlandpress.com

Citiraj ovu publikaciju:

Maraković, Nikola; Knežević, Anamarija; Rončević, Igor; Brazzolotto, Xavier; Kovarik, Zrinka; Šinko, Goran
Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases // Biochemical Journal, 477 (2020), 2771-2790 doi:10.1042/bcj20200192 (međunarodna recenzija, članak, znanstveni)
Maraković, N., Knežević, A., Rončević, I., Brazzolotto, X., Kovarik, Z. & Šinko, G. (2020) Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases. Biochemical Journal, 477, 2771-2790 doi:10.1042/bcj20200192.
@article{article, author = {Marakovi\'{c}, Nikola and Kne\v{z}evi\'{c}, Anamarija and Ron\v{c}evi\'{c}, Igor and Brazzolotto, Xavier and Kovarik, Zrinka and \v{S}inko, Goran}, year = {2020}, pages = {2771-2790}, DOI = {10.1042/bcj20200192}, keywords = {cholinesterase, hydroxyiminoacetamide, reactivation, stereoselectivity, PM7R6 method}, journal = {Biochemical Journal}, doi = {10.1042/bcj20200192}, volume = {477}, issn = {0264-6021}, title = {Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases}, keyword = {cholinesterase, hydroxyiminoacetamide, reactivation, stereoselectivity, PM7R6 method} }
@article{article, author = {Marakovi\'{c}, Nikola and Kne\v{z}evi\'{c}, Anamarija and Ron\v{c}evi\'{c}, Igor and Brazzolotto, Xavier and Kovarik, Zrinka and \v{S}inko, Goran}, year = {2020}, pages = {2771-2790}, DOI = {10.1042/bcj20200192}, keywords = {cholinesterase, hydroxyiminoacetamide, reactivation, stereoselectivity, PM7R6 method}, journal = {Biochemical Journal}, doi = {10.1042/bcj20200192}, volume = {477}, issn = {0264-6021}, title = {Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases}, keyword = {cholinesterase, hydroxyiminoacetamide, reactivation, stereoselectivity, PM7R6 method} }

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:





    Contrast
    Increase Font
    Decrease Font
    Dyslexic Font