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3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase


Odžak, Renata; Primožič, Ines; Tomić, Srđanka
3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase // Croatica Chemica Acta, 80 (2007), 1; 101-107 (međunarodna recenzija, članak, znanstveni)


Naslov
3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase

Autori
Odžak, Renata ; Primožič, Ines ; Tomić, Srđanka

Izvornik
Croatica Chemica Acta (0011-1643) 80 (2007), 1; 101-107

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

Ključne riječi
3-amidoquinuclidine; quaternary derivatives of 3-amidoquinuclidine; butyrylcholinesterase; chiral inhibitors

Sažetak
Racemates as well as (R)- and (S)-enantiomers of 3-pivalamidoquinuclidine (PivQ) and 3-acetamidoquinuclidine (AcQ) were prepared. Their quaternary racemic and enantiomerically pure N-benzyl derivatives (BnlPivQ and BnlAcQ) were synthesized as well. The amides were tested as substrates and inhibitors of butyrylcholinesterase (BChE) from horse serum (EC 3.1.1.8). No hydrolysis was observed under the experimental conditions used. On the contrary, the inhibition of BChE by (R)- and (S)-enantiomers of N-benzylquinuclidinium amides of pivalic acid was observed. The (S)-BnlPivQ with Ki=41.57 µ M was 3-fold more potent an inhibitor than the (R)-enantiomer. On the other hand both enantiomers of N-benzylquinuclidinum amides of acetic acid were shown to be inhibitors as well as activators depending on the concentrations of benzoylcholine (BzCh) which was used as a substrate of BChE.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

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


Uključenost u ostale bibliografske baze podataka:


  • Chemical Abstracts