Naslov
Antiproliferative and Antioxidant Activities of Synthetic, Tryptamine-Derived Granulatamide B and Its Structural Analogues

Autori
Matulja, Dario ; Grbčić, Petra ; Kraljević Pavelić, Sandra ; Marković, Dean

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
18th Hellenic Symposium on Medicinal Chemistry, Abstracts Book / - , 2021, 1-1

Skup
18th Hellenic Symposium on Medicinal Chemistry (HSMC-18)

Mjesto i datum
Atena, Grčka, 25.02.2021. - 27.02.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
granulatamide B, N-fatty acyl analogues, antiproliferative, antioxidant

Sažetak
Granulatamide B, a tryptamine-based alkaloid, characterized by unsaturated N-fatty acyl moiety, was previously isolated from organic extract of gorgonian coral, Eunicella granulata and found to exhibit high cytotoxicity against various cancer cell lines. In addition, numerous N-fatty acyl derivatives of tryptamine isolated from other natural resources or synthesized, showed significant anticancer, antibacterial or antioxidant activities. As part of the project, Bioprospecting of the Adriatic Sea, we have synthesized granulatamide B following the procedure of Fürstner’s Fe- catalyzed synthesis as well as structural analogues by the modification of the side chain (number of C-atoms, saturation degree and other structural modifications). Currently, total of seven compounds have been prepared and examined for antiproliferative and antioxidant activities applying MTT (3-(4, 5- dimethylthiazol-2-yl)-2, 5- diphenyltetrazolium bromide) and ABTS (2, 2'- azino-bis(3- ethylbenzothiazoline-6-sulfonic acid)) assays, respectively. Granulatamide B and analogues with chains of different lengths, but with the similar unsaturation pattern and isomeric configuration displayed the highest antiproliferative effect against SW620, CFPAC- 1, MCF-7 and HepG2 cancer cells with determined IC50 values in the range 25- 38 µM. Furthermore, all tested compounds showed promising antioxidant activities, especially those containing unsaturated fatty acid chains. The presented results highlight the importance of the indole skeleton as the pharmacophore group in medicinal chemistry and potential of fatty acid to modulate pharmacological properties of target molecules. Further studies regarding the synthesis of other derivatives, mechanism of action and/or screening for other biological activities of aforementioned compounds will be performed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Interdisciplinarne prirodne znanosti, Biotehnologija u biomedicini (prirodno područje, biomedicina i zdravstvo, biotehničko područje)

POVEZANOST RADA