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Pregled bibliografske jedinice broj: 1212105

Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity


Beus, Maja; Persoons, Leentje; Daelemans, Dirk; Schols, Dominique; Savijoki, Kirsi; Varmanen, Pekka; Yli‑Kauhaluoma, Jari; Pavić, Kristina; Zorc, Branka
Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity // Molecular diversity, 26 (2021), 2595-2612 doi:10.1007/s11030-021-10347-8 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1212105 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity

Autori
Beus, Maja ; Persoons, Leentje ; Daelemans, Dirk ; Schols, Dominique ; Savijoki, Kirsi ; Varmanen, Pekka ; Yli‑Kauhaluoma, Jari ; Pavić, Kristina ; Zorc, Branka

Izvornik
Molecular diversity (1381-1991) 26 (2021); 2595-2612

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

Ključne riječi
Anthranilamide ; · Quinoline ; β-Carboline ; Anticancer ; Antiviral ; Quorum sensing (QS) inhibition

Sažetak
In the present study, we report the design and synthesis of novel amide-type hybrid molecules based on anthranilic acid and quinoline or β- carboline heterocyclic scaffolds. Three types of biological screenings were performed: (i) in vitro antiproliferative screening against a panel of solid tumor and leukemia cell lines, (ii) antiviral screening against several RNA viruses, and (iii) anti-quorum sensing screening using gram-negative Chromobacterium violaceum as the reporter strain. Antiproliferative screening revealed a high activity of several compounds. Anthranilamides 12 and 13 with chloroquine core and halogenated anthranilic acid were the most active agents toward diverse cancer cell lines such as glioblastoma, pancreatic adenocarcinoma, colorectal carcinoma, lung carcinoma, acute lymphoblastic, acute myeloid, chronic myeloid leukemia, and non-Hodgkin lymphoma, but also against noncancerous cell lines. Boc-protected analogs 2 and 3 showed moderate activities against the tested cancer cells without toxic effects against noncancerous cells. A nonhalogenated quinoline derivative 10 with N-benzylanthranilic acid residue was equally active as 12 and 13 and selective toward tumor cells. Chloroquine and quinoline anthranilamides 10–13 exerted pronounced antiviral effect against human coronaviruses 229E and OC43, whereas 12 and 13 against coronavirus OC43 ( EC50 values in low micromolar range ; selectivity indices from 4.6 to > 10.4). Anthranilamides 14 and 16 with PQ core inhibited HIV-1 with EC50 values of 9.3 and 14.1 μM, respectively. Compound 13 displayed significant anti-quorum/biofilm effect against the quorum sensing reporter strain ( IC50 of 3.7 μM) with no apparent bactericidal effect.

Izvorni jezik
Engleski

Znanstvena područja
Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA


Projekti:
IP-2014-09-1501 - Dizajniranje, sinteza i evaluacija derivata primakina, vorinostata i sorafeniba kao potencijalnih citostatika (PVSderivatives) (HRZZ - 2014-09) ( CroRIS)

Profili:

Avatar Url Branka Zorc (autor)

Avatar Url Kristina Pavić (autor)

Avatar Url Maja Beus (autor)

Poveznice na cjeloviti tekst rada:

doi link.springer.com

Citiraj ovu publikaciju:

Beus, Maja; Persoons, Leentje; Daelemans, Dirk; Schols, Dominique; Savijoki, Kirsi; Varmanen, Pekka; Yli‑Kauhaluoma, Jari; Pavić, Kristina; Zorc, Branka
Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity // Molecular diversity, 26 (2021), 2595-2612 doi:10.1007/s11030-021-10347-8 (međunarodna recenzija, članak, znanstveni)
Beus, M., Persoons, L., Daelemans, D., Schols, D., Savijoki, K., Varmanen, P., Yli‑Kauhaluoma, J., Pavić, K. & Zorc, B. (2021) Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity. Molecular diversity, 26, 2595-2612 doi:10.1007/s11030-021-10347-8.
@article{article, author = {Beus, Maja and Persoons, Leentje and Daelemans, Dirk and Schols, Dominique and Savijoki, Kirsi and Varmanen, Pekka and Yli‑Kauhaluoma, Jari and Pavi\'{c}, Kristina and Zorc, Branka}, year = {2021}, pages = {2595-2612}, DOI = {10.1007/s11030-021-10347-8}, keywords = {Anthranilamide, · Quinoline, β-Carboline, Anticancer, Antiviral, Quorum sensing (QS) inhibition}, journal = {Molecular diversity}, doi = {10.1007/s11030-021-10347-8}, volume = {26}, issn = {1381-1991}, title = {Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity}, keyword = {Anthranilamide, · Quinoline, β-Carboline, Anticancer, Antiviral, Quorum sensing (QS) inhibition} }
@article{article, author = {Beus, Maja and Persoons, Leentje and Daelemans, Dirk and Schols, Dominique and Savijoki, Kirsi and Varmanen, Pekka and Yli‑Kauhaluoma, Jari and Pavi\'{c}, Kristina and Zorc, Branka}, year = {2021}, pages = {2595-2612}, DOI = {10.1007/s11030-021-10347-8}, keywords = {Anthranilamide, · Quinoline, β-Carboline, Anticancer, Antiviral, Quorum sensing (QS) inhibition}, journal = {Molecular diversity}, doi = {10.1007/s11030-021-10347-8}, volume = {26}, issn = {1381-1991}, title = {Anthranilamides with quinoline and β‑carboline scaffolds: design, synthesis, and biological activity}, keyword = {Anthranilamide, · Quinoline, β-Carboline, Anticancer, Antiviral, Quorum sensing (QS) inhibition} }

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:





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