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5-Iminodaunorubicin

Names

[ CAS No. ]:
67324-99-6

[ Name ]:
5-Iminodaunorubicin

[Synonym ]:
5-iminodaunorubicin hydrochloride
aromatic/heteroaromatic sulfonamide 14
5-Imino-4-methyl-4,5-dihydro-[1,3,4]thiadiazol-2-sulfonsaeure-amid
5-imino-4-methyl-4,5-dihydro-[1,3,4]thiadiazole-2-sulfonic acid amide
5-iminodaunomycin hydrochloride
1,3,4-Thiadiazole-2-sulfonamide,4,5-dihydro-5-imino-4-methyl

Biological Activity

[Description]:

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

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

In mouse leukemia L1210 cells, 5-Iminodaunorubicin produces protein-concealed DNA strand breaks. Many of the 5-iminodaunorubicin breaks may arise from apposed single-strand breaks (i.e., double-strand breaks)[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.

[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.

Chemical & Physical Properties

[ Density]:
1.51g/cm3

[ Boiling Point ]:
864.9ºC at 760 mmHg

[ Molecular Formula ]:
C27H31ClN2O9

[ Molecular Weight ]:
562.99600

[ Flash Point ]:
476.9ºC

[ Exact Mass ]:
562.17200

[ PSA ]:
192.62000

[ LogP ]:
2.81610

[ Index of Refraction ]:
1.698

Related Compounds