69895-68-7Relevant academic research and scientific papers
Enhancing the solubility of 1,4-diaminoanthraquinones in electrolytes for organic redox flow batteries through molecular modification
Binnemans, Koen,Dehaen, Wim,Evers, Jorik,Fransaer, Jan,Geysens, Pieter
, p. 39601 - 39610 (2020/11/13)
1,4-Diaminoanthraquinones (DAAQs) are a promising class of redox-active molecules for use in nonaqueous redox flow batteries (RFBs) because they can have up to five electrochemically accessible and reversible oxidation states. However, most of the commercially available DAAQs have a low solubility in the polar organic solvents that are typically used in RFBs, in particular when supporting electrolyte salts are present. This significantly limits the energy densities that can be achieved. We have functionalized the amino groups in the DAAQ structure with three types of chains, namely alkyl chains, cationic alkyl chains and oligoethylene glycol ether chains, and measured the solubility of these derivatives in various organic solvents by quantitative UV-Vis absorption spectroscopy. The DAAQ derivatives with higher polarity exhibit a significantly higher solubility in commonly used organic electrolytes in comparison to apolar derivatives. Cyclic voltammetry was used to assess the viability of the DAAQs as redox-active species for RFBs. Although the cationic DAAQ derivatives have an enhanced solubility in the electrolytes, the cathodic redox reactions have a poor reversibility, most likely due to an internal decomposition reaction of their reduced forms. The oligoethylene-glycol-ether-functionalized DAAQs are the most promising compounds for use in organic RFB electrolytes because they have the optimal combination of high solubility and a high reversibility of the redox couples. This journal is
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.
Near-IR region absorbing 1,4-diaminoanthracene-9,10-dione motif?based?ratiometric chemosensors for Cu2+
Kaur, Navneet,Kumar, Subodh
, p. 3168 - 3175 (2008/09/19)
1,4-Bis[2-aminoethylamino]anthracene-9,10-diones selectively bind with Cu2+ to form complexes with unusual selectivity under basic conditions. The deprotonation of the aryl amine NH in the case of these chemosensors causes a bathochromic shift in the absorption band from 585 nm and 635 nm to 725 nm and enables ratiometric estimation of Cu2+ between pH 8 and 12.
Synthesis and Antitumor Evaluations of Symmetrically and Unsymmetrically Substituted 1,4-Bisanthracene-9,10-diones and 1,4-Bis-5,8-dihydroxyanthracene-9,10-diones
Krapcho, A. Paul,Getahun, Zelleka,Avery, Kenneth L.,Vargas, Kevin J.,Hacker, Miles P.,et al.
, p. 2373 - 2380 (2007/10/02)
The ipso bis displacements of fluoride from 1,4-difluoroanthracene-9,10-dione (3) and 1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (4) by excess of a diamine (or a monoamine) in pyridine at room temperature lead to the symmetrically substituted 1,4-bis-substituted analogues 5 and 6, respectively.The ipso monodisplacements of fluoride from 3 and 4 can be accomplished by treatment with less than 1 molar equiv of a diamine (or a monoamine) to yield 7 and 8, respectively.Treatment of 7 or 8 with a different diamine leads to the unsymmetrically substituted1,4-bisanthracene-9,10-diones 9 and 10, respectively.Many of the synthetic unsymmetrical analogues have been evaluated for their antitumor activity against L1210 in vitro and in vivo.Cross resistance of analogue 10a with mitoxantrone (2) and doxorubicin was evaluated against MDR lines in vitro against human colon carcinoma LOVO and its subline resistant to DOXO (LOVO/DOXO).Potential mechanisms for the observed cytotoxicity are presented and discussed.
The Synthesis of 1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione and Ipso Substitutions of the Fluorides by Diamines Leading to 1,4-Bis--5,8-dihydroxyanthracene-9,10-diones
Krapcho, A. Paul,Getahun, Zelleka,Avery, Kenneth J.
, p. 2139 - 2146 (2007/10/02)
Two synthetic pathways to 1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (2) are described.The ipso substitution of the fluorides of 2 by diamines is a valuable preparative route to 1,4-bis-5,8-dihydroxyanthracene-9,10-diones related t
