Doxorubicinone  (Synonyms: Adriamycin aglycone; Adriamycinone)

Doxorubicinone (Adriamycin aglycone) is the aglycone of the antibiotic Doxorubicin (HY-15142A), i.e., its sugar-free parent nucleus structure. Doxorubicinone does not induce DNA damage or bind to RelA, but still downregulates the expression of pro-inflammatory cytokines (such as TNF, IL-12, etc.) regulated by the NF-κB pathway. Doxorubicinone can be used in sepsis-related research^[1][2][3].

Doxorubicinone (2 μM) weakly stabilizes CT DNA, increasing its melting temperature by 2.5 °C, which suggests minimal or no intercalation^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Doxorubicinone (i.p.; single dose) suppresses TNF secretion in a mouse sepsis model via a DNA damage-independent mechanism, with weaker potency than other tested anthracyclines^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

414.36

C₂₁H₁₈O₉

24385-10-2

Solid

Purple to purplish red

OC1=C(C2=C(C(C3=O)=C1C(C4=CC=CC(OC)=C34)=O)O)C[C@](O)(C[C@@H]2O)C(CO)=O

Room temperature in continental US; may vary elsewhere.

4°C, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

• [1]. Chora AF, et al. DNA damage independent inhibition of NF-κB transcription by anthracyclines. Elife. 2022;11:e77443. Published 2022 Dec 7.  [Content Brief]

  [2]. Tartakoff SS, et al. Investigations into the DNA-binding mode of doxorubicinone. Org Biomol Chem. 2019;17(7):1992-1998.  [Content Brief]

  [3]. Qian L, et al. Identification of Gut Bacterial Enzymes for Keto-Reductive Metabolism of Xenobiotics. ACS Chem Biol. 2022;17(7):1665-1671.  [Content Brief]