Sodium 1, 4-dihydroxy-9, 10-anthraquinone-2-sulphonate interacts with calf thymus DNA in a way that mimics anthracycline antibiotics: an electrochemical and spectroscopic study

被引：41

作者：

Guin, Partha Sarathi ^{[1
,2
]}

Das, Saurabh ^{[1
]}

Mandal, P. C. ^{[2
]}

机构：

[1] Jadavpur Univ, Dept Chem, Kolkata 700032, India

[2] Saha Inst Nucl Phys, Div Chem Sci, Kolkata 700064, India

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2010年 / 23卷 / 06期

关键词：

binding constant; binding site size; calf thymus DNA; chronocoulometry; fluorescence; sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate; square wave voltammetry; UV-Vis; DERIVATIVES; COMPLEXES; DAUNORUBICIN; DOXORUBICIN; POTENTIALS; ADRIAMYCIN; REDUCTION; BEHAVIOR; BINDING;

D O I：

10.1002/poc.1624

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anthracycline drugs, adriamycin and daunorubicin, efficient in the treatment of various human cancers, form strong intercalation complexes with DNA. The therapeutic efficiency and toxic properties of the drugs are associated with electron transfer processes, which correlate well with the redox behaviour of the compounds. Sodium 1,4-dihydroxy 9,10-anthraquinone-2-sulphonate (sodium quinizarin-2-sulphonate, NaLH2) (Na-Qz-2S) is a molecule that resembles anthracycline drugs and has a simpler structure in comparison to these drugs. Two electrons in the course of chemical action reduce this molecule like the anthracyclines. Electrochemical methods were used to identify this process. UV-Vis and fluorescence spectroscopy were used to analyse binding of the compound to calf thymus DNA. The binding constant and site size were evaluated for Na-Qz-2S and the same compared to that of the anthracyclines. Such comparisons are essential in order to understand whether the simpler hydroxy-anthraquinones can be a substitute for anthracycline drugs in cancer chemotherapy. Copyright (C) 2009 John Wiley & Sons, Ltd.

引用

页码：477 / 482

页数：6

共 38 条

[1] EFFECTS OF 7 ANTHRACYCLINE ANTIBIOTICS ON ELECTROCARDIOGRAM AND MITOCHONDRIAL-FUNCTION OF RAT HEARTS [J].

BACHMANN, E ;

WEBER, E ;

ZBINDEN, G .

AGENTS AND ACTIONS, 1975, 5 (04) :383-393

[2] Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity? [J].

Barasch, D ;

Zipori, O ;

Ringel, I ;

Ginsburg, I ;

Samuni, A ;

Katzhendler, J .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (7-8) :597-615

[3]

Bard A. J., Electrochemical Methods

[4] SUBSTITUENT EFFECTS UPON THE PEAK POTENTIALS AND REDUCTIVE CLEAVAGE RATE CONSTANTS OF HYDROXY-SUBSTITUTED AND METHOXY-SUBSTITUTED 9,10-ANTHRAQUINONES IN 50-PERCENT AQUEOUS CH3CN - DO THEY CORRELATE [J].

BLANKESPOOR, RL ;

KOSTERS, EL ;

POST, AJ ;

VANMEURS, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1609-1614

[5]

Cantor C., 1980, Biophysical Chemistry, V2

[6] Interaction of mithramycin and chromomycin A3 with d(TAGCTAGCTA)2:: Role of sugars in antibiotic-DNA recognition [J].

Chakrabarti, S ;

Bhattacharyya, B ;

Dasgupta, D .

JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (27) :6947-6953

[7] Inclusion of the parent molecules of some drugs with β-cyclodextrin studied by electrochemical and spectrometric methods [J].

Dang, XJ ;

Nie, MY ;

Tong, J ;

Li, HL .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1998, 448 (01) :61-67

[8] Studies on the formation of Cu(II) and Ni(II) complexes of 1,2-dihydroxy-9,10-anthraquinone and lack of stimulated superoxide formation by the complexes [J].

Das, S ;

Saha, A ;

Mandal, PC .

TALANTA, 1996, 43 (01) :95-102

[9] Some applications of electrochemistry in biomedical chemistry. Emphasis on the correlation of electrochemical and bioactive properties [J].

de Abreu, FC ;

Ferraz, PAD ;

Goulart, MOF .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2002, 13 (01) :19-35

[10]

DURR FE, 1984, SEMIN ONCOL, V11, P3

← 1 2 3 4 →