81-60-7Relevant articles and documents
Interaction of anthraquinone anti-cancer drugs with DNA:Experimental and computational quantum chemical study
Al-Otaibi, Jamelah S.,Teesdale Spittle, Paul,El Gogary, Tarek M.
, p. 751 - 760 (2016/09/07)
Anthraquinones form the basis of several anticancer drugs. Anthraquinones anticancer drugs carry out their cytotoxic activities through their interaction with DNA, and inhibition of topoisomerase II activity. Anthraquinones (AQ4 and AQ4H) were synthesized and studied along with 1,4-DAAQ by computational and experimental tools. The purpose of this study is to shade more light on mechanism of interaction between anthraquinone DNA affinic agents and different types of DNA. This study will lead to gain of information useful for drug design and development. Molecular structures were optimized using DFT B3LYP/6-31?+?G(d). Depending on intramolecular hydrogen bonding interactions two conformers of AQ4 were detected and computed as 25.667?kcal/mol apart. Molecular reactivity of the anthraquinone compounds was explored using global and condensed descriptors (electrophilicity and Fukui functions). Molecular docking studies for the inhibition of CDK2 and DNA binding were carried out to explore the anti cancer potency of these drugs. NMR and UV-VIS electronic absorption spectra of anthraquinones/DNA were investigated at the physiological pH. The interaction of the three anthraquinones (AQ4, AQ4H and 1,4-DAAQ) were studied with three DNA (calf thymus DNA, (Poly[dA].Poly[dT]) and (Poly[dG].Poly[dC]). NMR study shows a qualitative pattern of drug/DNA interaction in terms of band shift and broadening. UV-VIS electronic absorption spectra were employed to measure the affinity constants of drug/DNA binding using Scatchard analysis.
Antitumor Agents-CLXVII. Synthesis and structure-activity correlations of the cytotoxic anthraquinone 1,4-bis-(2,3-epoxypropylamino)-9,10-anthracenedione, and of related compounds
Johnson, Mary G.,Kiyokawa, Hiroshi,Tani, Shohei,Koyama, Junko,Morris-Natschke, Susan L.,Mauger, Anthony,Bowers-Daines, Margaret M.,Lange, Barry C.,Lee, Kuo-Hsiung
, p. 1469 - 1479 (2007/10/03)
1,4-Bis-(2,3-epoxypropylamino)-9,10-anthracenedione (3) was synthesized in this laboratory and was found to be a potent antitumor agent. Derivatives of this compound containing anthraquinone, naphthoquinone, and quinone skeletons were also prepared and evaluated for in vitro cytotoxic activity in several cell lines. These molecules were designed as bifunctional antitumor agents with the potential to act as (1) intercalating agents due to their planar backbones, and (2) alkylating agents due to the presence of alkylating moieties in their side chains. Compounds with an anthraquinone skeleton and propylamino side chains containing epoxides or halohydrins as the alkylating species showed greater activity than similar compounds with naphthoquinone or quinone skeletons. Compounds without these alkylating functionalities (e.g., with alkene or amino groups) were generally inactive. Hydroxy substitution on the planar skeleton in conjunction with alkylating side chains gave compounds with the most potent cytotoxic activity. The position of the hydroxy groups and side chains could be varied without substantially affecting activity. Activity was retained when an epoxypropyloxy side chain was substituted for the epoxypropylamino side chain in the parent compound.
Liquid Crystalline Triptycene Derivatives
Norvez, Sophie
, p. 2414 - 2418 (2007/10/02)
A route to triptycenes substituted with one, two, five, and six paraffinic chains was developed using the Diels-Alder reaction as the key reaction. 1,4,5,8-Tetrakis(dodecyloxy)-11-hydroxy-14-(dodecanoyloxy)triptycene, 1,4,5,8-tetrakis(dodecyloxy)-11,14-bis(dodecanoyloxy)triptycene, and 1,4,5,8,11,14-hexakis(dodecyloxy)triptycene were obtained in a nine-step procedure starting from diaminoanthrarufin.The five-chain derivative demonstrates original mesomorphic properties.
