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72983-78-9

72983-78-9 Structure

72983-78-9 Structure
IdentificationBack Directory
[Name]

5(8H)-Naphthacenone, 8-acetyl-10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, (8S,10S)-
[CAS]

72983-78-9
[Synonyms]

NSC-254681
5-Iminodaunomycin
5-iminodaunorubicin
(8S)-12-Imino-8-acetyl-10α-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8α,11-trihydroxy-1-methoxynaphthacene-5(12H)-one
(8S,10S)-7,9,10,12-Tetrahydro-8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-6,8,11-trihydroxy-12-imino-1-methoxy-5(8H)-naphthacenone
5(8H)-Naphthacenone, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, (8S,10S)-
5(8H)-Naphthacenone, 8-acetyl-10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, (8S,10S)-
[Molecular Formula]

C27H30N2O9
[MOL File]

72983-78-9.mol
[Molecular Weight]

526.54
Chemical PropertiesBack Directory
[Boiling point ]

747.6±60.0 °C(Predicted)
[density ]

1.62±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[form ]

Solid
[pka]

7.77±0.60(Predicted)
[color ]

Purple to black
Hazard InformationBack Directory
[Uses]

5-Iminodaunorubicin is a quinone-modified anthracycline that retains antitumor activity[1]. 5-Iminodaunorubicin produces protein-concealed DNA strand breaks in cancer cells[2].
[in vivo]

In rat, 5-Iminodaunorubicin (5-ID; 1-16 mg/kg) treatment produces widening of the QRS complex, increased R- and S-wave voltage, and prolonged the Q alpha T interval. And the quinone redox cycling is suppressed in 5-Iminodaunorubicin. 5-Iminodaunorubicin shows lower cardiotoxic[1].

[References]

[1] R A Jensen, et al. Electrocardiographic and transmembrane potential effects of 5-iminodaunorubicin in the rat. Cancer Res. 1984 Sep;44(9):4030-9. PMID:6744318
[2] L A Zwelling, et al. Cytotoxicity and DNA strand breaks by 5-iminodaunorubicin in mouse leukemia L1210 cells: comparison with adriamycin and 4'-(9-acridinylamino)methanesulfon-m-anisidide. Cancer Res. 1982 Jul;42(7):2687-91. PMID:6896293
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