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

Napredna pretraga

Pregled bibliografske jedinice broj: 992935

Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity


Petrović Peroković, Vesna; Car, Željka; Usenik, Andrea; Opačak-Bernardi, Teuta; Jurić, Andrea; Tomić, Srđanka
Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity // Molecular diversity, 24 (2019), 1; 253-263 doi:10.1007/s11030-019-09948-1 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 992935 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity

Autori
Petrović Peroković, Vesna ; Car, Željka ; Usenik, Andrea ; Opačak-Bernardi, Teuta ; Jurić, Andrea ; Tomić, Srđanka

Izvornik
Molecular diversity (1381-1991) 24 (2019), 1; 253-263

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

Ključne riječi
Kojic acid ; Maltol ; Adamantyl ; Antiproliferation ; Cancer

Sažetak
Pyran-4-one (maltol, kojic acid and chlorokojic acid 1) esters of adamantan-1-ylacetic acid were prepared through eicient synthetic routes in good yields and evaluated for their in vitro antiproliferative activity on four cancer cell lines: K562 (chronic myelogenous leukemia), HeLa (cervical cancer), Caco-2 (colorectal adenocarcinoma) and NCI-H358 (bronchioalveolar carcinoma). The results indicate that the presence and the position of the adamantyl acyl group or chlorine atom are the necessary requirement for antitumor activity of pyranone systems. Derivatives of kojic acid with either free (compounds 1 and 8) or acylated 5-OH group (compounds 2 and 9) have shown good-to-moderate activity (IC50 values ranging from 13.1 to 43.0 μM) on all cell lines. Adamantyl kojic acid derivative 5 with a free OH group on the position 2 showed activity only on the K562 cell line. It seems that removal of halogen or adamantyl unit from position 2 elicits antileukemic activity, as observed in compound 5. The positive inluence of the adamantyl unit was also observed on a 3-OH acylated derivative of maltol I which was also selectively active on the same cell line. 5-O- benzylated adamantyl compounds 6 and 7 and unmodiied starting pyranones were found to be inactive. Antibacterial activity of compounds was also evaluated on S. aureus ATCC 13709, M. catarrhalis ATCC 23246, E. faecalis ATCC29212 and E. coli TolC-Tn10, but no activity was observed (MIC values 128–256 μg/mL).

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2014-09-7899 - Sinteza, strukturna analiza i biološka evaluacija peptidomimetika i glikonjugata (PEPTGLYCOSAR) (Tomić-Pisarović, Srđanka, HRZZ - 2014-09) ( POIROT)

Ustanove:
Prirodoslovno-matematički fakultet, Zagreb,
Medicinski fakultet, Osijek,
Sveučilište u Osijeku - Odjel za kemiju

Citiraj ovu publikaciju

Petrović Peroković, Vesna; Car, Željka; Usenik, Andrea; Opačak-Bernardi, Teuta; Jurić, Andrea; Tomić, Srđanka
Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity // Molecular diversity, 24 (2019), 1; 253-263 doi:10.1007/s11030-019-09948-1 (međunarodna recenzija, članak, znanstveni)
Petrović Peroković, V., Car, Ž., Usenik, A., Opačak-Bernardi, T., Jurić, A. & Tomić, S. (2019) Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity. Molecular diversity, 24 (1), 253-263 doi:10.1007/s11030-019-09948-1.
@article{article, year = {2019}, pages = {253-263}, DOI = {10.1007/s11030-019-09948-1}, keywords = {Kojic acid, Maltol, Adamantyl, Antiproliferation, Cancer}, journal = {Molecular diversity}, doi = {10.1007/s11030-019-09948-1}, volume = {24}, number = {1}, issn = {1381-1991}, title = {Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity}, keyword = {Kojic acid, Maltol, Adamantyl, Antiproliferation, Cancer} }

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