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Pregled bibliografske jedinice broj: 1003049

Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase


Bosak, Anita; Opsenica, Dejan M.; Šinko, Goran; Zlatar, Matija; Kovarik, Zrinka
Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase // Chemico-Biological Interactions, 308 (2019), 101-109 doi:10.1016/j.cbi.2019.05.024 (međunarodna recenzija, članak, znanstveni)


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Naslov
Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase

Autori
Bosak, Anita ; Opsenica, Dejan M. ; Šinko, Goran ; Zlatar, Matija ; Kovarik, Zrinka

Izvornik
Chemico-Biological Interactions (0009-2797) 308 (2019); 101-109

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

Ključne riječi
Cholinesterase ; Alzheimer's disease ; pKa value ; Quinoline-based compounds ; Selectivity

Sažetak
Eight derivatives of 4-aminoquinolines differing in the substituents attached to the C(4)-amino group and C(7) were synthesised and tested as inhibitors of human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Both enzymes were inhibited by all of the compounds with inhibition constants (Ki) ranging from 0.50 to 50 μM exhibiting slight selectivity toward AChE over BChE. The most potent inhibitors of AChE were compounds with an n-octylamino chain or adamantyl group. The shortening of the chain length resulted in a decrease in AChE inhibition by 5–20 times. Docking studies revealed that the quinoline group within the AChE active site was positioned in the choline binding site, while the C(4)-amino group substituents, depending on their lipophilicity, could establish hydrogen bonds or π-interactions with residues of the peripheral anionic site. The most potent inhibitors of BChE were compounds with the most voluminous substituent on C(4)-amino group (adamantyl) or those with a stronger electron withdrawing substituent on C(7) (trifluormethyl group). Based on AChE inhibition, compounds with an n-octylamino chain or adamantyl substituent were shown to possess the capacity for further development as potential drugs for treatment of neurodegenerative diseases.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekti:
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

Profili:

Avatar Url Goran Šinko (autor)

Avatar Url Zrinka Kovarik (autor)

Avatar Url Anita Bosak (autor)

Citiraj ovu publikaciju

Bosak, Anita; Opsenica, Dejan M.; Šinko, Goran; Zlatar, Matija; Kovarik, Zrinka
Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase // Chemico-Biological Interactions, 308 (2019), 101-109 doi:10.1016/j.cbi.2019.05.024 (međunarodna recenzija, članak, znanstveni)
Bosak, A., Opsenica, D., Šinko, G., Zlatar, M. & Kovarik, Z. (2019) Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase. Chemico-Biological Interactions, 308, 101-109 doi:10.1016/j.cbi.2019.05.024.
@article{article, year = {2019}, pages = {101-109}, DOI = {10.1016/j.cbi.2019.05.024}, keywords = {Cholinesterase, Alzheimer's disease, pKa value, Quinoline-based compounds, Selectivity}, journal = {Chemico-Biological Interactions}, doi = {10.1016/j.cbi.2019.05.024}, volume = {308}, issn = {0009-2797}, title = {Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase}, keyword = {Cholinesterase, Alzheimer's disease, pKa value, Quinoline-based compounds, Selectivity} }
@article{article, year = {2019}, pages = {101-109}, DOI = {10.1016/j.cbi.2019.05.024}, keywords = {Cholinesterase, Alzheimer's disease, pKa value, Quinoline-based compounds, Selectivity}, journal = {Chemico-Biological Interactions}, doi = {10.1016/j.cbi.2019.05.024}, volume = {308}, issn = {0009-2797}, title = {Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase}, keyword = {Cholinesterase, Alzheimer's disease, pKa value, Quinoline-based compounds, Selectivity} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
  • Scopus
  • MEDLINE


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