5-Iminodaunorubicin hydrochloride is a quinone-modified anthracycline active molecule with anti-tumor activity. 5-Iminodaunorubicin hydrochloride causes strand breaks in DNA in cancerous cells.

Physicochemical Properties

Molecular Formula	C27H31CLN2O9
Molecular Weight	563.00
Exact Mass	562.172
CAS #	67324-99-6
Related CAS #	5-Iminodaunorubicin;72983-78-9
PubChem CID	72399
Appearance	Purple to black solid powder
Density	1.51g/cm3
Boiling Point	864.9ºC at 760 mmHg
Flash Point	476.9ºC
Index of Refraction	1.698
LogP	2.816
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Heavy Atom Count	39
Complexity	963
Defined Atom Stereocenter Count	6
SMILES	C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl
InChi Key	BLLIIPIJZPKUEG-HPTNQIKVSA-N
InChi Code	InChI=1S/C27H30N2O9/c1-10-23(31)14(28)7-17(37-10)38-16-9-27(35,11(2)30)8-13-19(16)26(34)20-21(25(13)33)24(32)12-5-4-6-15(36-3)18(12)22(20)29/h4-6,10,14,16-17,23,29,31,33-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,23+,27-/m0/s1
Chemical Name	(8S,10S)-8-acetyl-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one
Synonyms	5-Iminodaunorubicin hydrochloride
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	5-Iminodaunorubicin causes protein-concealed DNA strand breaks in murine leukemia L1210 cells. Apposed single-strand breaks, or double-strand breaks, may be the source of many 5-iminodaunorubicin breaks[2].
ln Vivo	5-Iminodaunorubicin (5-ID; 1–16 mg/kg) therapy widens the QRS complex, raises the voltage of the R- and S-waves, and lengthens the Q alpha T interval in rats. Additionally, 5-Iminodaunorubicin suppresses the quinone redox cycle. 5-Iminodaunorubicin exhibits reduced cardiotoxicity [1].
References	[1]. Electrocardiographic and transmembrane potential effects of 5-iminodaunorubicin in the rat. Cancer Res. 1984 Sep;44(9):4030-9. [2]. 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.

Solubility Data

Solubility (In Vitro)

DMSO : ~230 mg/mL (~408.5 mM) H2O : ~8.3 mg/mL (~14.8 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 5 mg/mL (8.88 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (8.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.7762 mL	8.8810 mL	17.7620 mL
	5 mM	0.3552 mL	1.7762 mL	3.5524 mL
	10 mM	0.1776 mL	0.8881 mL	1.7762 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.