Protein Information

Name complex is
Synonyms 39kD; CI 39kD; Complex I; Complex I 39kD; NADH dehydrogenase (ubiquinone) Fe S protein 2 like; NADH ubiquinone oxidoreductase 39 kDa subunit mitochondrial; NADH ubiquinone oxidoreductase 39 kDa subunit; NDUFA 9…

Compound Information

Name anthraquinone
CAS 9,10-anthracenedione

Reference List

PubMed Abstract RScore(About this table)
9467063 Das S, Saha A, Mandal PC: Radiation-induced double-strand modification in calf thymus DNA in the presence of 1,2-dihydroxy-9,10-anthraquinone and its Cu (II) complex. Environ Health Perspect. 1997 Dec;105 Suppl 6:1459-62.

Our results show that the Cu (II)-DHA complex is more efficient in modifying the base-pair region in double-stranded DNA compared to free DHA.
1(0,0,0,1) Details
18754611 Zagotto G, Sissi C, Lucatello L, Pivetta C, Cadamuro SA, Fox KR, Neidle S, Palumbo M: Aminoacyl-anthraquinone conjugates as telomerase inhibitors: synthesis, biophysical and biological evaluation. J Med Chem. 2008 Sep 25;51(18):5566-74.

The telomerase-telomere complex is a prospective anticancer target.
1(0,0,0,1) Details
8431447 van Houte LP, van Garderen CJ, Patel DJ: The antitumor drug nogalamycin forms two different intercalation complexes with d (GCGT).d (ACGC). Biochemistry. 1993 Feb 16;32(6):1667-74.

In complex I, the aglycon ring of the drug stacks with the C6-G7 bases, and the sugars are directed to the G1.C8 end; while in the case of complex II the anthraquinone ring system is stacked with C2-G3 bases, and the sugars are pointed to the T4.A5 base pair end.
32(0,1,1,2) Details
3165639 Rizzo V, Penco S, Menozzi M, Geroni C, Vigevani A, Arcamone F: Studies of anthracycline--DNA complexes by circular dichroism. Anticancer Drug Des. 1988 Aug;3(2):103-15.

Conformational correspondence with the known structure of the daunorubicin-oligonucleotide complex is inferred from the spectra of derivatives with modifications at position 6 or 11 in the anthraquinone chromophore.
31(0,1,1,1) Details
7639535 Malisza KL, Hasinoff BB: Production of hydroxyl radical by iron (III)-anthraquinone complexes through self-reduction and through reductive activation by the xanthine oxidase/hypoxanthine system. Arch Biochem Biophys. 1995 Aug 1;321(1):51-60.

The rate of self-reduction of the iron (III)-doxorubicin complex is consistent with a mechanism in which unbound doxorubicin binds to an iron (III)-doxorubicin complex of decreased coordination and after binding undergoes an intramolecular electron transfer.
1(0,0,0,1) Details
15824924 Kalayda GV, Jansen BA, Wielaard P, Tanke HJ, Reedijk J: Dinuclear platinum anticancer complexes with fluorescent N,N'-bis (aminoalkyl)-1,4-diaminoanthraquinones: cellular processing in two cisplatin-resistant cell lines reflects the differences in their resistance profiles. J Biol Inorg Chem. 2005 May;10(3):305-15. Epub 2005 Apr 12.

The platinum complex is excreted from the cell via the Golgi apparatus, while the weakly basic anthraquinone ligand accumulates in the Golgi complex, where it is taken up by lysosomes and then transported to the cell surface.
31(0,1,1,1) Details
19853921 Guin PS, Das S, Mandal PC: Studies on the formation of a complex of Cu (II) with sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate - an analogue of the core unit of anthracycline anticancer drugs and its interaction with calf thymus DNA. J Inorg Biochem. 2009 Dec;103(12):1702-10. Epub 2009 Sep 29.

The 1:2 metal-ligand complex is formed in aqueous solution at neutral and acidic pH while in alkaline pH both 1:1 and 1:2 species are formed.
2(0,0,0,2) Details
9296455 Gille L, Nohl H: Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. Free Radic Biol Med. 1997;23(5):775-82.

After one-electron transfer to the parent hydrophilic anthraquinone molecule destabilization of the radical formed causes cleavage of the sugar residue.
This enzyme that is associated with complex I of the respiratory chain catalyzes the oxidation of cytosolic NADH.
1(0,0,0,1) Details
18966468 Das S, Saha A, Mandal PC: Studies on the formation of Cu (II) and Ni (II) complexes of l,2-dihydroxy-9,10-anthraquinone and lack of stimulated superoxide formation by the complexes. Talanta. 1996 Jan;43(1):95-102.

The effective stability constant of the Cu (II) complex is 5.135 x 10 (29) while that of the Ni (II) complex is 3.446 x 10 (25).
1(0,0,0,1) Details
3094197 Wallace KB: Nonenzymatic oxygen activation and stimulation of lipid peroxidation by doxorubicin-copper. Toxicol Appl Pharmacol. 1986 Oct;86(1):69-79.

The data demonstrate that despite the implication of hydrogen peroxide and hydroxyl radicals in doxorubicin-copper stimulated lipid peroxidation, the immediate product of dioxygen reduction by the complex is superoxide-free radicals.
The suggested occurrence of doxorubicin-copper complexes in vivo infers that nonenzymatic generation of oxygen-free radicals by the chelate may contribute to the mechanism of toxicity of doxorubicin and related anthraquinone anticancer agents observed clinically.
1(0,0,0,1) Details
566070 Bouhet JC, Pham van Chuong P: Specific and non-specific interactions of two carcinogenic mycotoxins, luteoskyrin and rugulosin with nucleic acids. Ann Nutr Aliment. 1977;31(4-6):811-30.

(-) Luteoskyrin and (+) Rugulosin are 2 hepatotoxic and carcinogenic anthraquinone-like pigments from Penicillia which contaminate rice and other foodstuffs.
In the present work, characterization, specificity and structure of binary polychelates (pigment-metal) n and ternary complexes (pigment-metal-nucleic acids) are successively reported: whereas, unspecific complex II with double-stranded polynucleotides is shown to result from simple adsorption of polychelate onto the double helix, complex I is specific for single-stranded DNA (or polypurine nucleotides) and results from electrostatic association of separate pigment-metal units with the polyphosphate chain.
1(0,0,0,1) Details
2400540 Morier-Teissier E, Bernier JL, Lohez M, Catteau JP, Henichart JP: Free radical production and DNA cleavage by copper chelating peptide-anthraquinones. Anticancer Drug Des. 1990 Aug;5(3):291-305.

Two pseudopeptides incorporating a peptide metal-chelating moiety (Gly-His-Lys) and a polyhydroxy anthraquinone ring related to the nuclei of anti-tumor drugs such as mitoxantrone and ametantrone, have been synthesized.
This latter complex is able to induce DNA breakage at a high level.
1(0,0,0,1) Details
8517915 Jeziorek D, Dyl D, Liwo A, Woznicki W, Tempczyk A, Borowski E: A theoretical study of the mechanism of oxygen binding by model anthraquinones. Anticancer Drug Des. 1993 Jun;8(3):223-35.

It was found that the oxygen-binding site is determined by three factors: the high electron density and high HOMO coefficients on the carbon atoms to which oxygen binds, the minimum loss of conjugation within the anthraquinone moiety on oxygen binding and the minimum number of bonds to other heavy atoms of the oxygen-binding carbons (the steric effect).
For different molecules, the energy of the most stable oxygen complex is the greatest for compounds with the lowest ionization potential.
1(0,0,0,1) Details