Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety

Murat Bingul, Owen Tan, Christopher R. Gardner, Selina K. Sutton, Greg M. Arndt, Glenn M. Marshall, Belamy B. Cheung, Naresh Kumar, David St C. Black

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Identification of the novel (E)-N1-((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 G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.

LanguageEnglish
Article number916
Number of pages19
JournalMolecules
Volume21
Issue number7
DOIs
Publication statusPublished - 1 Jul 2016
Externally publishedYes

Fingerprint

hydrazides
quinoline
cancer
Cells
Derivatives
synthesis
Neuroblastoma
cultured cells
Neoplasms
Cyclin-Dependent Kinase Inhibitor p27
multiple docking adapters
G1 Phase Cell Cycle Checkpoints
Cell Line
Hydrazones
Cell Cycle Proteins
hydrazones
cycles
Carboxylic Acids
viability
methylene

Bibliographical note

Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • Anticancer
  • Breast cancer
  • Hydrazide-hydrazone
  • Neuroblastoma
  • Quinoline

Cite this

Bingul, M., Tan, O., Gardner, C. R., Sutton, S. K., Arndt, G. M., Marshall, G. M., ... Black, D. S. C. (2016). Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety. Molecules, 21(7), [916]. https://doi.org/10.3390/molecules21070916
Bingul, Murat ; Tan, Owen ; Gardner, Christopher R. ; Sutton, Selina K. ; Arndt, Greg M. ; Marshall, Glenn M. ; Cheung, Belamy B. ; Kumar, Naresh ; Black, David St C. / Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety. In: Molecules. 2016 ; Vol. 21, No. 7.
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Bingul, M, Tan, O, Gardner, CR, Sutton, SK, Arndt, GM, Marshall, GM, Cheung, BB, Kumar, N & Black, DSC 2016, 'Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety', Molecules, vol. 21, no. 7, 916. https://doi.org/10.3390/molecules21070916

Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety. / Bingul, Murat; Tan, Owen; Gardner, Christopher R.; Sutton, Selina K.; Arndt, Greg M.; Marshall, Glenn M.; Cheung, Belamy B.; Kumar, Naresh; Black, David St C.

In: Molecules, Vol. 21, No. 7, 916, 01.07.2016.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Marshall, Glenn M.

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AU - Kumar, Naresh

AU - Black, David St C.

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Y1 - 2016/7/1

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