Document Type

Journal Article

Authors

Qiwei Wang, Department of Chemistry, Centre for Advanced Luminescence Materials, Hong Kong Baptist University
Marcus Chun-Wah Yuen, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Guo-Liang Lu, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Cheuk-Lam Ho, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Gui-Jiang Zhou, Department of Chemistry, Centre for Advanced Luminescence Materials, Hong Kong Baptist University
Oi-Mei Keung, Department of Chemistry, Centre for Advanced Luminescence Materials, Hong Kong Baptist University
Kim-Hung Lam, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Roberto Gambari, BioPharmaNet, Department of Biochemistry and Molecular Biology, University of Ferrara
Xiao-Ming Tao, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Raymond Siu-Ming Wong, Haematology Division, Department of Medicine and Therapeutics, Prince of Wales Hospital
See-Wai Tong, Haematology Division, Department of Medicine and Therapeutics, Prince of Wales Hospital
Kit-Wah Chan, Haematology Division, Department of Medicine and Therapeutics, Prince of Wales Hospital
Fung-Yi Lau, Haematology Division, Department of Medicine and Therapeutics, Prince of Wales Hospital
Filly Cheung, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Gregory Yin-Ming Cheng, Haematology Division, Department of Medicine and Therapeutics, Prince of Wales Hospital
Chung-Hin Chui, Institute of Textiles and Clothing, Hong Kong Polytechnic University
Wai-Yeung Wong, Department of Chemistry, Centre for Advanced Luminescence Materials, Hong Kong Baptist UniversityFollow

Department/Unit

Department of Chemistry

Title

Synthesis of 9,9-dialkyl-4,5-diazafluorene derivatives and their structure–activity relationships toward human carcinoma cell lines

Language

English

Abstract

A homologous set of 9,9-dialkyl-4,5-diazafluorene compounds were prepared by alkylation of 4,5-diazafluorene with the appropriate alkyl bromide and under basic conditions. The structures of these simple organic compounds were confirmed by spectroscopic techniques (FTIR, NMR, and FABMS). Their biological effects toward a panel of human carcinoma cells, including Hep3B hepatocellular carcinoma, MDAMB-231 breast carcinoma, and SKHep-1 hepatoma cells, were investigated; a structure-activity correlation was established with respect to the length of the alkyl chain and the fluorene ring structure. The relationship between the mean potency [log(1/IC50)] and alkyl chain length was systematically studied. The results show that compounds with butyl, hexyl, and octyl chains exhibit good growth inhibitory effects toward these three human carcinoma cell lines, and the 9,9-dihexyl-4,5-diazafluorene further exhibits antitumor activity in athymic nude mice Hep3B xenograft models. For the structurally related dialkylfluorenes that lack the diaza functionality, in vitro cytotoxicity was not observed at clinically relevant concentrations. © 2010 Wiley-VCH Verlag GmbHand Co. KGaA, Weinheim.

Keywords

Cytotoxicity, Diazafluorenes, Hepatoma, Synthesis, Xenografts

Publication Date

2010

Source Publication Title

ChemMedChem

Volume

5

Issue

4

Start Page

559

End Page

566

Publisher

Wiley-VCH Verlag

DOI

10.1002/cmdc.201000034

Link to Publisher's Edition

http://dx.doi.org/10.1002/cmdc.201000034

ISSN (print)

18607179

ISSN (electronic)

18607187

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