Login

Doxorubicinone

Doxorubicinone is a metabolite of the anthracycline antitumor antibiotic doxorubicin.<sup class="referenceList">[1],[2]</sup> Doxorubicinone inhibits mitochondrial succinoxidase from bovine heart and reduces the mitochondrial inner membrane potential in rat heart and liver mitochondria in a concentration-dependent manner.<sup class="referenceList">[3],[4]</sup> Doxorubicinone (40 μM) increases pentose phosphate pathway flux by 45% and reduces activity of glutathione peroxidase (GPx) and superoxide dismutase (SOD) by 17 and 60%, respectively, in human erythrocytes.<sup class="referenceList">[5]</sup> It also induces cytotoxicity in patient-derived ovarian cancer colonies in a concentration-dependent manner.<sup class="referenceList">[2]</sup>
24385-10-2
Item No.
TX006X6Z
CAS No.
24385-10-2
Molecular Formula
C21H18O9
Molecular Weight
414.3622
Pricing ＆ Availability
Pack Size Purity Price(USD) Availability Quantity
1mg ≥98% $111.00 in stock
5mg $220.00 in stock
10mg $362.00 in stock
WARNING This product is for research use only. SDS
Technical Information
Item No.:
TX006X6Z
Product Name:
Doxorubicinone
Description:
Synonyms:
Adriamycin aglycone; Adriamycinone; aglycone-DOX; Doxorubicin aglycone; Epirubicin aglycone; Doxorubicinone
CAS Number:
24385-10-2
MDL:
MFCD00871832
Molecular Formula:
C21H18O9
Molecular Weight:
414.3622
SMILES:
OC1=C(C[C@](C(CO)=O)(O)C[C@@H]2O)C2=C(O)C(C3=O)=C1C(C4=CC=CC(OC)=C34)=O
λmax:
234, 252, 288, 496 nm
Solubility:
DMF: 5 mg/ml, DMSO: 5 mg/ml, Ethanol: 5 mg/ml
Shipping Condition:
Room temperature in continental US; may vary elsewhere.
References & Citations:
[1]. 1.Patel, S., Sprung, A.U., Keller, B.A., et al. Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: Implications for the mechanisms of doxorubicin action and cytotoxicity Mol. Pharmacol. 52(4),658-666 (1997).
[2]. Ozols, R.F., Willson, J.K.V., Weltz, M.D., et al. Inhibition of human ovarian cancer colony formation by adriamycin and its major metabolites Cancer Res. 40(11),4109-4112 (1980).
[3]. Kishi, T., Watanabe, T., and Folkers, K. Bioenergetics in clinical medicine: Prevention by forms of coenzyme Q of the inhibition by adriamycin of coenzyme Q10-enzymes in mitochondria of the myocardium Proc. Natl. Acad. Sci. USA 73(12),4653-4656 (1976).
[4]. Al-Nasser, I.A. Prevention of adriamycin aglycone-induced changes of inner mitochondrial membrane permeability by cyclosporin A Med. Sci. Res. 25(4),249-251 (1997).
[5]. Misiti, F., Giardina, B., Mordente, A., et al. The secondary alcohol and aglycone metabolites of doxorubicin alter metabolism of human erythrocytes Braz. J. Med. Biol. Res. 36(12),1643-1651 (2003).