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Pregled bibliografske jedinice broj: 575778

Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors


Gredičak, Matija; Abramić, Marija; Jerić, Ivanka
Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors // Amino acids (Wien), 43 (2012), 5; 2087-2100 doi:10.1007/s00726-012-1292-0 (međunarodna recenzija, članak, znanstveni)


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Naslov
Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors

Autori
Gredičak, Matija ; Abramić, Marija ; Jerić, Ivanka

Izvornik
Amino acids (Wien) (0939-4451) 43 (2012), 5; 2087-2100

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

Ključne riječi
aminopeptidase N; enediyne-peptide conjugate; enzyme inhibitors; amino acids

Sažetak
Enediyne-peptide conjugates were designed with the aim to inhibit aminopeptidase N, a widespread ectoenzyme with a variety of functions, like protein digestion, inactivation of cytokines in the immune system and endogenous opioid peptides in the central nervous system. Enediyne moiety was embedded within the 12-membered ring with hydrophobic amino acid alanine, valine, leucine or phenylalanine used as carriers. Aromatic part of the enediyne bridging unit and the amino acid side-chains were considered pharmacophores for the binding to the APN active site. Additionally, the fused enediyne-amino acid "heads" were bound through a flexible linker to the L-lysine, an amino group donor. The synthesis included building the aromatic enediyne core at the C-terminal of amino acids and subsequent intramolecular N- alkylation. APN inhibition test revealed that the alanine-based derivative 9a inhibits the APN with IC50 of 34 ± 11 M. Enediyne-alanine conjugate 12 missing the flexible linker was much less effective in the APN inhibition. These results show that enediyne-fused amino acids have potential as new pharmacophores in the design of APN inhibitors.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
098-0982933-2936 - Kemijske preobrazbe prirodnih spojeva (Varga-Defterdarović, Lidija, MZOS ) ( POIROT)
098-1191344-2938 - Molekularna enzimologija i proteinske interakcije hidrolaza (Abramić, Marija, MZOS ) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Matija Gredičak (autor)

Avatar Url Marija Abramić (autor)

Avatar Url Ivanka Jerić (autor)

Citiraj ovu publikaciju

Gredičak, Matija; Abramić, Marija; Jerić, Ivanka
Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors // Amino acids (Wien), 43 (2012), 5; 2087-2100 doi:10.1007/s00726-012-1292-0 (međunarodna recenzija, članak, znanstveni)
Gredičak, M., Abramić, M. & Jerić, I. (2012) Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors. Amino acids (Wien), 43 (5), 2087-2100 doi:10.1007/s00726-012-1292-0.
@article{article, year = {2012}, pages = {2087-2100}, DOI = {10.1007/s00726-012-1292-0}, keywords = {aminopeptidase N, enediyne-peptide conjugate, enzyme inhibitors, amino acids}, journal = {Amino acids (Wien)}, doi = {10.1007/s00726-012-1292-0}, volume = {43}, number = {5}, issn = {0939-4451}, title = {Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors}, keyword = {aminopeptidase N, enediyne-peptide conjugate, enzyme inhibitors, amino acids} }
@article{article, year = {2012}, pages = {2087-2100}, DOI = {10.1007/s00726-012-1292-0}, keywords = {aminopeptidase N, enediyne-peptide conjugate, enzyme inhibitors, amino acids}, journal = {Amino acids (Wien)}, doi = {10.1007/s00726-012-1292-0}, volume = {43}, number = {5}, issn = {0939-4451}, title = {Cyclic Enediyne-Amino Acid Chimeras as New Aminopeptidase N Inhibitors}, keyword = {aminopeptidase N, enediyne-peptide conjugate, enzyme inhibitors, amino acids} }

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


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