Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety

被引:64
作者
Bingul, Murat [1 ,2 ]
Tan, Owen [2 ]
Gardner, Christopher R. [1 ,2 ]
Sutton, Selina K. [2 ]
Arndt, Greg M. [2 ,3 ]
Marshall, Glenn M. [2 ,4 ]
Cheung, Belamy B. [2 ]
Kumar, Naresh [1 ]
Black, David StC. [1 ]
机构
[1] Univ New South Wales Australia, Sch Chem, Sydney, NSW 2052, Australia
[2] Univ New South Wales Australia, Childrens Canc Inst Australia Med Res, Lowy Canc Res Ctr, Sydney, NSW 2031, Australia
[3] Univ New South Wales Australia, Childrens Canc Inst Australia Med Res, ACRF Drug Discovery Ctr Childhood Canc, Lowy Canc Res Ctr, Sydney, NSW 2052, Australia
[4] Sydney Childrens Hosp, Kids Canc Ctr, Randwick, NSW 2031, Australia
来源
MOLECULES | 2016年 / 21卷 / 07期
基金
澳大利亚国家健康与医学研究理事会; 澳大利亚研究理事会;
关键词
quinoline; hydrazide-hydrazone; anticancer; neuroblastoma; breast cancer; SUBEROYLANILIDE HYDROXAMIC ACID; KINASE INHIBITOR P27; HISTONE DEACETYLASE INHIBITOR; ANTIPROLIFERATIVE EVALUATION; CYTOTOXIC ACTIVITY; HUMAN CANCER; LUNG-CANCER; DNA-BINDING; APOPTOSIS; LEUKEMIA;
D O I
10.3390/molecules21070916
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Identification of the novel (E)-N-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio)propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19-26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G(1) cell cycle arrest, as well as upregulation of the p27(kip1) cell cycle regulating protein.
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页数:19
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