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Pregled bibliografske jedinice broj: 1030240

Antitumor and antiviral activities of 4- substituted 1, 2, 3-triazolyl-2, 3-dibenzyl-L- ascorbic acid derivatives


Meščić Macan, Andrijana; Harej, Anja; Cazin, Ines; Klobučar, Marko; Stepanić, Višnja; Pavelić, Krešimir; Kraljević Pavelić, Sandra; Schols, Dominique; Snoeck, Robert; Andrei, Graciela; Raić-Malić, Silvana
Antitumor and antiviral activities of 4- substituted 1, 2, 3-triazolyl-2, 3-dibenzyl-L- ascorbic acid derivatives // European journal of medicinal chemistry, 184 (2019), 111739, 17 doi:10.1016/j.ejmech.2019.111739 (međunarodna recenzija, članak, znanstveni)


Naslov
Antitumor and antiviral activities of 4- substituted 1, 2, 3-triazolyl-2, 3-dibenzyl-L- ascorbic acid derivatives

Autori
Meščić Macan, Andrijana ; Harej, Anja ; Cazin, Ines ; Klobučar, Marko ; Stepanić, Višnja ; Pavelić, Krešimir ; Kraljević Pavelić, Sandra ; Schols, Dominique ; Snoeck, Robert ; Andrei, Graciela ; Raić-Malić, Silvana

Izvornik
European journal of medicinal chemistry (0223-5234) 184 (2019); 111739, 17

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

Ključne riječi
Vitamin C ; Butenolide ; 1, 2, 3-Triazole ; HIF-1 ; NOS2 ; Antitumoral ; Antiviral activity

Sažetak
Two series of 6-(1, 2, 3-triazolyl)-2, 3- dibenzyl- l-ascorbic acid derivatives with the hydroxyethylene (8a−8u) and ethylidene linkers (10c−10p) were synthesized and evaluated for their antiproliferative activity against seven malignant tumor cell lines and antiviral activity against a broad range of viruses. Conformationally unrestricted spacer between the lactone and 1, 2, 3-triazole units in 8a−8u series had a profound effect on antitumor activity. Besides, the introduction of a long side chain at C-4 of 1, 2, 3-triazole that led to the synthesis of decyl-substituted 2, 3- dibenzyl-l- ascorbic acid 8m accounted for a selective and potent antiproliferative activity on breast cancer MCF-7 cells cells in the nM range. Further analysis showed that compound 8m strongly enhanced expression of hypoxia inducible transcription factor 1 α (HIF-1α) and to some extent decreased expression of nitric oxide synthase 2 (NOS2) suggesting its role in regulating HIF-1α signalling pathway. The p- methoxyphenyl-substituted derivative 10g displayed specific anti-cytomegalovirus (CMV) potential, whereas aliphatic-substituted derivatives 8l and 8m had the most potent, yet relatively non-specific, anti-varicella-zoster (VZV) activity

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2018-01-4682 - Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja (Silvana Raić-Malić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb,
Sveučilište u Rijeci - Odjel za biotehnologiju

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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