Synthesis and biological evaluation of quinoline derivatives as potential anti-prostate cancer agents and Pim-1 kinase inhibitors

Li, Kun; Liu, Ying; Zhou, Di; Fan, Yinbo; Guo, Hongye; Ma, Tianyi; Wen, Jiachen; Liu, Dan; Zhao, Liang

doi:10.1016/j.bmc.2016.03.016

Cited by 61 publications

(16 citation statements)

References 23 publications

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“…8-hydroxyquinoline (HQ) is a well-studied, privileged structure, with activity against a wide range of cell types (Prachayasittikul, Prachayasittikul, Ruchirawat, & Prachayasittikul, 2013;Song, Xu, Chen, Zhan, & Liu, 2015), including anticancer activity (Barilli et al, 2014;Bhat, Shim, Zhang, Chong, & Liu, 2012;Chang, Chen, Wang, Tzeng, & Chen, 2010;Feng et al, 2015;Li et al, 2016;Moret et al, 2009;Mrozek-Wilczkiewicz et al, 2015;Sosi c et al, 2013;Spaczy nska, Tabak, Malarz, & Musiol, 2014), antifungal activity (Cieslik et al, 2012;Musiol et al, 2006), and antibacterial activity (Warner, Musto, Turesky, & Soloway, 1975). The HQ are active against several bacterial species including Staphylococcus aureus and Staphylococcus epidermidis (Abouelhassan et al, 2014(Abouelhassan et al, , 2015Basak et al, 2016;Garrison et al, 2017;Lam et al, 2014), Enterococcus faecium (Basak et al, 2016;Garrison et al, 2017), Burkholderia pseudomallei (Wangtrakuldee et al, 2013), Neisseria gonorrhoeae, (Lawung et al, 2018), Listeria monocytogenes (Cherdtrakulkiat et al, 2016), and Mycobacterium avium (Hongmanee, Rukseree, Buabut, Somsri, & Palittapongarnpim, 2007;Kos et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

Odingo

Early

Smith

et al. 2019

Drug Development Research

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There is an urgent need for new treatments effective against Mycobacterium tuberculosis, the causative agent of tuberculosis. The 8‐hydroxyquinoline series is a privileged scaffold with anticancer, antifungal, and antibacterial activities. We conducted a structure–activity relationship study of the series regarding its antitubercular activity using 26 analogs. The 8‐hydroxyquinolines showed good activity against M. tuberculosis, with minimum inhibitory concentrations (MIC90) of <5 μM for some analogs. Small substitutions at C5 resulted in the most potent activity. Substitutions at C2 generally decreased potency, although a sub‐family of 2‐styryl‐substituted analogs retained activity. Representative compounds demonstrated bactericidal activity against replicating M. tuberculosis with >4 log kill at 10× MIC over 14 days. The majority of the compounds demonstrated cytotoxicity (IC50 of <100 μM). Further development of this series as antitubercular agents should address the cytotoxicity liability. However, the 8‐hydroxyquinoline series represents a useful tool for chemical genomics to identify novel targets in M. tuberculosis.

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Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

Odingo

Early

Smith

et al. 2019

Drug Development Research

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“…Proto-oncogene serine/threonine-protein kinase pim-1 (pim-1) is a proto-oncogene encoded by the pim-1 gene (8). It has been reported that pim-1 serves important roles in apoptosis, proliferation and differentiation of cancer cells and the progression of cancer (9).…”

Section: Introductionmentioning

confidence: 99%

Reduced pim‑1 expression increases chemotherapeutic drug sensitivity in human androgen‑independent prostate cancer cells by inducing apoptosis

et al. 2019

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Chemotherapeutic drug resistance is an obstacle for the successful therapy of prostate cancer. The aim of the present study was to identify the effects of proto-oncogene serine/threonine-protein kinase pim-1 (pim-1) in the proliferation of chemotherapeutic drug-resistant prostate cancer cells. Androgen-independent human prostate cancer cell lines PC3 and DU145 were used in the current study. Cisplatin-sensitive PC3 cells and cisplatin-resistant PC3/DDP cells were used in drug-resistance assays. The expression levels of pim-1, permeability glycoprotein (p-gp), caspase-3 and cleaved caspase-3 were determined using western blotting analysis; pim-1 was knocked down using pim-1-specific short hairpin RNA (shRNA); cell viability was determined using MTT assay and IC 50 values of the chemotherapeutic drugs in human prostate cancer cells tested were calculated using GraphPad 5 software. Androgen-independent human prostate cancer cell lines PC3 and DU145 were transfected with pim-1-targeted or control shRNA, and MTT results revealed that pim-1 knockdown significantly inhibited PC3 and DU145 cell viability in a time-dependent manner (P<0.01). Cisplatin-resistant cells PC3/DDP exhibited higher levels of pim-1 and p-gp expression compared with cisplatin-sensitive PC3 cells; and pim-1 knockdown markedly increased chemotherapeutic drug sensitivity in PC3/DDP cells. In addition, pim-1 knockdown increased chemotherapeutic drug sensitivity in PC3/DDP cells. The molecular mechanism of drug sensitivity was discovered to be partly due to pim-1 knockdown, as it significantly increased apoptosis in cisplatin-resistant PC3/DDP cells. The present study may provide a new strategy for the therapy of prostate cancer.

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“…Li et al have been synthesized quinoline derivatives as PIM-1 kinase inhibitors in the treatment of prostate cancer. [12] In another study, Fan et al have shown the synthesis of substituted pyrido[3, 2-d]-1,2,3-triazines as potential PIM-1 kinase inhibitors. They have shown the essential binding sites such as LYS 67, ASP 128, and PHE 49 [13] for the interaction of ligands with the PIM-1 kinase.…”

Section: Introductionmentioning

confidence: 99%

Virtual Screening, Molecular Docking, and DFT Studies of Some Thiazolidine‐2,4‐diones as Potential PIM‐1 Kinase Inhibitors

et al. 2018

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In the present study, ZINC database has been used for virtual screening of thousand of compounds based on previously reported pharmacophore against PIM-1 kinase. These compounds were further screened by Glide docking methodologies such as high throughput virtual screening (HTVS), standard precision (SP) and extra precision (XP), against PIM-1 kinase (PDB ID: 4DTK). Eight top-ranked compounds ZINC22066185, ZINC05678245, ZINC16431468, ZINC05773728, ZINC36633741, ZINC16779084, ZINC19909862 and ZINC15056464, were selected by virtual screening and docking studies. These compounds were showed better binding affinities towards PIM-1 kinase by using amino acid residues such as LYS67, GLU171, ASP128, and ASP186. The top-ranked compounds were showed their predicted binding energies with PIM-1 kinase in the range of À9.06, À8.45, À8.96, À8.78, À8.63, À8.56, À8.56 and À8.30 kcal/mol, respectively. Various reference ligands of PDB ID: 4DTK, 3VBQ and 3VC4, were also taken for docking study on protein kinase (PDB ID: 4DTK) to find out the comparative Glide score of receptor ligand complexes. To confirm the inhibitors potencies, the orbital energies, such as HOMO and LUMO, of the hit compounds were calculated. The results of the study showed that ZINC22066185 and ZINC16779084, may be considered as prototype compounds for further development of potential PIM-1 inhibitors.

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Synthesis and biological evaluation of quinoline derivatives as potential anti-prostate cancer agents and Pim-1 kinase inhibitors

Cited by 61 publications

References 23 publications

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

Reduced pim‑1 expression increases chemotherapeutic drug sensitivity in human androgen‑independent prostate cancer cells by inducing apoptosis

Virtual Screening, Molecular Docking, and DFT Studies of Some Thiazolidine‐2,4‐diones as Potential PIM‐1 Kinase Inhibitors

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