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Synthesis, Crystallographic, Quantum Chemical, Antitumor, and Molecular Docking/Dynamic Studies of 4-Hydroxycoumarin-Neurotransmitter Derivatives

DS. Dimić, GN. Kaluđerović, EH. Avdović, DA. Milenković, MN. Živanović, I. Potočňák, E. Samoľová, MS. Dimitrijević, L. Saso, ZS. Marković, JM. Dimitrić Marković

. 2022 ; 23 (2) : . [pub] 20220117

Jazyk angličtina Země Švýcarsko

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc22011308

Grantová podpora
TumorSelCoum 6388843 Science Fund of the Republic of Serbia (Serbian Science and Diaspora Collaboration Program: Knowledge Exchange Vouchers)
451-03-9/2021-14/200378, 51-03-09/2021-14/200122, and 451-03-68/2020-14/200146 Ministry of Education, Science and Technological Development of the Republic of Serbia
CZ.2.16/3.1.00/24510 Operation program Prague Competitiveness
VEGA 1/0148/19. Slovak grant agencies

In this contribution, four new compounds synthesized from 4-hydroxycoumarin and tyramine/octopamine/norepinephrine/3-methoxytyramine are characterized spectroscopically (IR and NMR), chromatographically (UHPLC-DAD), and structurally at the B3LYP/6-311++G*(d,p) level of theory. The crystal structure of the 4-hydroxycoumarin-octopamine derivative was solved and used as a starting geometry for structural optimization. Along with the previously obtained 4-hydroxycoumarin-dopamine derivative, the intramolecular interactions governing the stability of these compounds were quantified by NBO and QTAIM analyses. Condensed Fukui functions and the HOMO-LUMO gap were calculated and correlated with the number and position of OH groups in the structures. In vitro cytotoxicity experiments were performed to elucidate the possible antitumor activity of the tested substances. For this purpose, four cell lines were selected, namely human colon cancer (HCT-116), human adenocarcinoma (HeLa), human breast cancer (MDA-MB-231), and healthy human lung fibroblast (MRC-5) lines. A significant selectivity towards colorectal carcinoma cells was observed. Molecular docking and molecular dynamics studies with carbonic anhydrase, a prognostic factor in several cancers, complemented the experimental results. The calculated MD binding energies coincided well with the experimental activity, and indicated 4-hydroxycoumarin-dopamine and 4-hydroxycoumarin-3-methoxytyramine as the most active compounds. The ecotoxicology assessment proved that the obtained compounds have a low impact on the daphnia, fish, and green algae population.

Citace poskytuje Crossref.org

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