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Pregled bibliografske jedinice broj: 1244152

Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking

Krstulović, Luka; Leventić, Marijana; Rastija, Vesna Rastija; Kristina Starčević; Jirouš, Maja; Janić, Ivana; Karnaš, Maja; Lasić, Kornelija; Bajić, Miroslav; Glavaš-Obrovac, Ljubica
Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking // Molecules, 28 (2023), 28020540, 28 doi:10.3390/ molecules28020 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 1244152 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking

Autori
Krstulović, Luka ; Leventić, Marijana ; Rastija, Vesna Rastija ; Kristina Starčević ; Jirouš, Maja ; Janić, Ivana ; Karnaš, Maja ; Lasić, Kornelija ; Bajić, Miroslav ; Glavaš-Obrovac, Ljubica

Izvornik
Molecules (1420-3049) 28 (2023); 28020540, 28

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

Ključne riječi
aminoquinoline-benzimidazole hybrids ; anticancer ; in silico ADME, docking ; cell-cycle perturba-tion ; mitochondrial membrane potential ; apoptosis

Sažetak
In this study, new 7‐chloro‐4‐aminoquinoline‐ benzimidazole compounds were synthesized and characterized by NMR, MS, and elemental analysis. These novel hybrids differ in the type of linker and in the substituent on the benzimidazole moiety. Their antiproliferative activities were evaluated on one non‐tumor (MDCK1) and seven selected tumor (CaCo‐2, MCF‐7, CCRF‐CEM, Hut78, THP‐1, and Raji) cell lines by MTT test and flow cytometry analysis. The compounds with different types of linkers and an unsubstituted benzimidazole ring, 5d, 8d, and 12d, showed strong cytotoxic activity (the GI50 ranged from 0.4 to 8 μM) and effectively suppressed the cell cycle progression in the leukemia and lymphoma cells. After 24 h of treatment, compounds 5d and 12d induced the disruption of the mitochondrial membrane potential as well as apoptosis in HuT78 cells. The drug‐like properties and bioavailability of the compounds were calculated using the Swiss ADME web tool, and a molecular docking study was performed on tyrosine‐protein kinase c‐Src (PDB: 3G6H). Compound 12d showed good solubility and permeability and bound to c‐Src with an energy of −119.99 kcal/mol, forming hydrogen bonds with Glu310 and Asp404 in the active site and other residues with van der Waals interactions. The results suggest that compound 12d could be a leading compound in the further design of effective antitumor drugs.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA

Ustanove:
Veterinarski fakultet, Zagreb,
Fakultet agrobiotehničkih znanosti Osijek,
Medicinski fakultet, Osijek

Profili:

Avatar Url Maja Karnaš (autor)

Avatar Url Miroslav Bajić (autor)

Avatar Url Vesna Rastija (autor)

Avatar Url Maja Jirouš (autor)

Avatar Url Ljubica Glavaš Obrovac (autor)

Avatar Url Kristina Starčević (autor)

Avatar Url Luka Krstulović (autor)

Poveznice na cjeloviti tekst rada:

Pristup cjelovitom tekstu rada doi

Citiraj ovu publikaciju:

Krstulović, Luka; Leventić, Marijana; Rastija, Vesna Rastija; Kristina Starčević; Jirouš, Maja; Janić, Ivana; Karnaš, Maja; Lasić, Kornelija; Bajić, Miroslav; Glavaš-Obrovac, Ljubica
Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking // Molecules, 28 (2023), 28020540, 28 doi:10.3390/ molecules28020 (međunarodna recenzija, članak, znanstveni)
Krstulović, L., Leventić, M., Rastija, V., Kristina Starčević, Jirouš, M., Janić, I., Karnaš, M., Lasić, K., Bajić, M. & Glavaš-Obrovac, L. (2023) Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking. Molecules, 28, 28020540, 28 doi:10.3390/ molecules28020.
@article{article, author = {Krstulovi\'{c}, Luka and Leventi\'{c}, Marijana and Rastija, Vesna Rastija and Jirou\v{s}, Maja and Jani\'{c}, Ivana and Karna\v{s}, Maja and Lasi\'{c}, Kornelija and Baji\'{c}, Miroslav and Glava\v{s}-Obrovac, Ljubica}, year = {2023}, pages = {28}, DOI = {10.3390/ molecules28020}, chapter = {28020540}, keywords = {aminoquinoline-benzimidazole hybrids, anticancer, in silico ADME, docking, cell-cycle perturba-tion, mitochondrial membrane potential, apoptosis}, journal = {Molecules}, doi = {10.3390/ molecules28020}, volume = {28}, issn = {1420-3049}, title = {Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking}, keyword = {aminoquinoline-benzimidazole hybrids, anticancer, in silico ADME, docking, cell-cycle perturba-tion, mitochondrial membrane potential, apoptosis}, chapternumber = {28020540} }
@article{article, author = {Krstulovi\'{c}, Luka and Leventi\'{c}, Marijana and Rastija, Vesna Rastija and Jirou\v{s}, Maja and Jani\'{c}, Ivana and Karna\v{s}, Maja and Lasi\'{c}, Kornelija and Baji\'{c}, Miroslav and Glava\v{s}-Obrovac, Ljubica}, year = {2023}, pages = {28}, DOI = {10.3390/ molecules28020}, chapter = {28020540}, keywords = {aminoquinoline-benzimidazole hybrids, anticancer, in silico ADME, docking, cell-cycle perturba-tion, mitochondrial membrane potential, apoptosis}, journal = {Molecules}, doi = {10.3390/ molecules28020}, volume = {28}, issn = {1420-3049}, title = {Novel 7-chloro-4-aminoquinoline-benzimidazole hybrids as inhibitors of cancer cells growth: synthesis, antiproliferative activity, in silico ADME predictions, and docking}, keyword = {aminoquinoline-benzimidazole hybrids, anticancer, in silico ADME, docking, cell-cycle perturba-tion, mitochondrial membrane potential, apoptosis}, chapternumber = {28020540} }

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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