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Pregled bibliografske jedinice broj: 1041288

Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents


Racané, Livio; Ptiček, Lucija; Fajdetić, Glorija; Tralić-Kulenović, Vesna; Klobučar, Marko; Kraljević Pavelić, Sandra; Perić, Mihaela; Čipčić Paljetak, Hana; Verbanac, Donatella; Starčević, Kristina
Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents // Bioorganic chemistry, 95 (2020), 103537, 10 doi:10.1016/j.bioorg.2019.103537 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1041288 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents

Autori
Racané, Livio ; Ptiček, Lucija ; Fajdetić, Glorija ; Tralić-Kulenović, Vesna ; Klobučar, Marko ; Kraljević Pavelić, Sandra ; Perić, Mihaela ; Čipčić Paljetak, Hana ; Verbanac, Donatella ; Starčević, Kristina

Izvornik
Bioorganic chemistry (0045-2068) 95 (2020); 103537, 10

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

Ključne riječi
green synthesis ; benzothiazoles ; antitumor activity ; antibacterial activity ; antioxidative activity ; HIF-1 protein

Sažetak
We present a new efficient green synthetic protocol for introduction of substituents to the C-6 position of 2-arylbenzothiazole nuclei. Newly synthesized compounds were designed to study the influence of the hydroxy and methoxy groups on the 2-arylbenzothiazole scaffold, as well as the influence of the type of substituents placed on the C-6 position of benzothiazole moiety on biological activity, including antibacterial, antitumor and antioxidant activity. Modest activity was observed against the tested Gram-positive and Gram-negative bacterial strains for only amidino derivatives 5d and 6d. The tested compounds exhibited moderate to strong antiproliferative activity towards the tumor cell lines tested. The SAR study revealed that the introduction of substituents into the benzene ring of the benzothiazole nuclei is essential for antiproliferative activity, while introduction of the hydroxy group into the 2- aryl moiety of the 2-arybenzothiazole scaffold significantly improved selectivity against tumor cell lines. The observed results revealed several novel 6-substituted-2-arylbenzothiazole compounds, 5b, 5c, 5f and 6f, with strong and selective antiproliferative activity towards HeLa cells in micro and submicromolar concentrations, with the most selective compounds being 6-ammonium-2-(2- hydroxy/methoxyphenyl)benzothiazoles 5f and 6f. The compound 5f bearing the hydroxy group on the 2-arylbenzothiazole core showed the most promising antioxidative activity evaluated by DPPH, ABTS and FRAP in vitro assays. The presence of the amino protonated group attached at the benzothiazole moiety was essential for the antiproliferative and antioxidant activity observed, exerted through a change in the levels of the reactive oxygen species-modulated HIF-1 protein.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA


Projekti:
HRZZ-IP-2016-06-3163 - Lipidi hrane, spol i dob u patogenezi metaboličkog sindroma (DietMetSyn) (Starčević, Kristina, HRZZ - 2016-06) ( POIROT)
HRZZ-IP-2018-01-4379 - Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa (AntioxPot) (Hranjec, Marijana, HRZZ - 2018-01) ( POIROT)

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb,
Veterinarski fakultet, Zagreb,
Medicinski fakultet, Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Sveučilište u Rijeci - Odjel za biotehnologiju

Citiraj ovu publikaciju

Racané, Livio; Ptiček, Lucija; Fajdetić, Glorija; Tralić-Kulenović, Vesna; Klobučar, Marko; Kraljević Pavelić, Sandra; Perić, Mihaela; Čipčić Paljetak, Hana; Verbanac, Donatella; Starčević, Kristina
Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents // Bioorganic chemistry, 95 (2020), 103537, 10 doi:10.1016/j.bioorg.2019.103537 (međunarodna recenzija, članak, znanstveni)
Racané, L., Ptiček, L., Fajdetić, G., Tralić-Kulenović, V., Klobučar, M., Kraljević Pavelić, S., Perić, M., Čipčić Paljetak, H., Verbanac, D. & Starčević, K. (2020) Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents. Bioorganic chemistry, 95, 103537, 10 doi:10.1016/j.bioorg.2019.103537.
@article{article, year = {2020}, pages = {10}, DOI = {10.1016/j.bioorg.2019.103537}, chapter = {103537}, keywords = {green synthesis, benzothiazoles, antitumor activity, antibacterial activity, antioxidative activity, HIF-1 protein}, journal = {Bioorganic chemistry}, doi = {10.1016/j.bioorg.2019.103537}, volume = {95}, issn = {0045-2068}, title = {Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents}, keyword = {green synthesis, benzothiazoles, antitumor activity, antibacterial activity, antioxidative activity, HIF-1 protein}, chapternumber = {103537} }
@article{article, year = {2020}, pages = {10}, DOI = {10.1016/j.bioorg.2019.103537}, chapter = {103537}, keywords = {green synthesis, benzothiazoles, antitumor activity, antibacterial activity, antioxidative activity, HIF-1 protein}, journal = {Bioorganic chemistry}, doi = {10.1016/j.bioorg.2019.103537}, volume = {95}, issn = {0045-2068}, title = {Green synthesis and biological evaluation of 6- substituted-2-(2- hydroxy/methoxyphenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents}, keyword = {green synthesis, benzothiazoles, antitumor activity, antibacterial activity, antioxidative activity, HIF-1 protein}, chapternumber = {103537} }

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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