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ChemicalBook--->CAS DataBase List--->1361644-26-9

1361644-26-9

1361644-26-9 Structure

1361644-26-9 Structure
IdentificationBack Directory
[Name]

INNO206
[CAS]

1361644-26-9
[Synonyms]

Aldoxorubicin
Aldoxorubicin (INNO-206)
Aldoxorubicin Aldoxorubicin
N-[(E)-[1-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide
(E)-N’-[1-[(2S,4S)-4-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-2-tetrahydropyranyl]oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-tetracenyl]-2-hydroxyethylidene]-6-(2,5-dioxo-2,5-dihydro-1-pyrrolyl)hexanehydrazide
[Molecular Formula]

C37H42N4O13
[MOL File]

1361644-26-9.mol
[Molecular Weight]

750.75
Chemical PropertiesBack Directory
[density ]

1.60±0.1 g/cm3(Predicted)
[storage temp. ]

-80°, stored under nitrogen,unstable in solution, ready to use.
[solubility ]

DMSO : 75 mg/mL (99.90 mM)
[form ]

Solid
[pka]

7.36±0.60(Predicted)
[color ]

Purple to purplish red
Safety DataBack Directory
[Symbol(GHS) ]


GHS08
[Signal word ]

Danger
[Hazard statements ]

H340-H350-H360
Hazard InformationBack Directory
[Uses]

Aldoxorubicin (INNO-206) is an albumin-binding proagent of Doxorubicin (DNA topoisomerase II inhibitor), which is released from albumin under acidic conditions. Aldoxorubicin (INNO-206) has potent antitumor activities in various cancer cell lines and in murine tumor models.
[Biological Activity]

Aldoxorubicin (INNO-206) is an albumin-bound prodrug of doxorubicin, a DNA topoisomerase II inhibitor, released from albumin under acidic conditions. It has potent antitumor activity in various cancer cell lines and mouse tumor models.
[in vitro]

Aldoxorubicin (INNO-206) (0.27 to 2.16 μM) inhibits blood vessel formation and reduces multiple myeloma cell growth in a pH-dependent fashion.
[in vivo]

Aldoxorubicin (INNO-206) (10.8 mg/kg, i.v.) shows significantly smaller tumor volumes and IgG levels on days 28, and is well tolerated with 90% of mice surviving until the termination of the study in the mice bearing the LAGκ-1A tumor.
[target]

Topoisomerase II

Daunorubicins/Doxorubicins

[IC 50]

Topoisomerase II; Daunorubicins/Doxorubicins
[storage]

-80°, stored under nitrogen,unstable in solution, ready to use.
[References]

[1] Eric Sanchez, et al. Anti-Myeloma Effects of the Novel Anthracycline Derivative INNO-206. Clin Cancer Res.2012 18; 3856.
[2] Kratz, F. INNO-206 (DOXO-EMCH), an Albumin-Binding Prodrug of Doxorubicin Under Development for Phase II Studies. Current Bioactive Compounds, 2011, 7(1): 33-38(6)
[3] Graeser R, et al. INNO-206, the (6-maleimidocaproyl hydrazone derivative of doxorubicin), shows superior antitumor efficacy compared to doxorubicin in different tumor xenograft models and in an orthotopic pancreas carcinoma model. Invest New Drugs. 2010 F DOI:10.1007/s10637-008-9208-2
[4] Walker L, et al. Cell penetrating peptides fused to a thermally targeted biopolymer drug carrier improve the delivery and antitumor efficacy of an acid-sensitive doxorubicin derivative. Int J Pharm. 2012 Oct 15;436(1-2):825-32. DOI:10.1016/j.ijpharm.2012.07.043
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