CAS 75443-99-1|Aclarubicin hydrochloride

Introduction:Basic information about CAS 75443-99-1|Aclarubicin hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameAclarubicin hydrochloride
CAS Number75443-99-1Molecular Weight848.329
Density/Boiling Point897.7ºC at 760 mmHg
Molecular FormulaC42H54ClNO15Melting Point151-153℃
MSDS/Flash Point496.7ºC

Names

Namemethyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate,hydrochloride
SynonymMore Synonyms

Aclarubicin hydrochloride BiologicalActivity

DescriptionAclacinomycin A hydrochloride (Aclarubicin hydrochloride), a fluorescent molecule, is an effective anthracycline chemotherapeutic agent for hematologic cancers and solid tumors. Accumulates efficiently in the mitochondria of living human cells and leads to mitochondrial dysfunction[1].
Related CatalogResearch Areas >>CancerSignaling Pathways >>Others >>Others
In VitroAclacinomycin A (Acla) results in an yellow solution. Aclacinomycin A could efficiently enter living cells and emit fluorescence in situ. Aclacinomycin A reveals that 10 μM Aclacinomycin A for 15 min is sufficient for clear detection of fluorescence in most of the cultured cells. Aclacinomycin A treatment (10 μM Acla for 15 min) results in approximately 20% dead (or nearly dead) cells[1]. Aclacinomycin A (Aclarubicin) effectively induces incorporation of exon 7 into SMN2 transcripts from the endogenous gene in type I SMA fibroblasts as well as into transcripts from a SMN2 minigene in the motor neuron cell line NSC34. In type I fibroblasts, treatment results in an increase in SMN protein and gems to normal levels[2]. Aclarubicin is shown to inhibit binding of topoisomerase II (Y to its DNA substrate in vitro and increases the amount of extractable topoisomerase II α[3].
References

[1]. Iihoshi H, et al. Aclarubicin, an anthracycline anti-cancer drug, fluorescently contrasts mitochondria and reduces the oxygen consumption rate in living human cells. Toxicol Lett. 2017 Aug 5;277:109-114.

[2]. Andreassi C, et al. Aclarubicin treatment restores SMN levels to cells derived from type I spinal muscular atrophy patients. Hum Mol Genet. 2001 Nov 15;10(24):2841-9.

[3]. Sehested M, et al. Mapping of DNA topoisomerase II poisons (etoposide, clerocidin) and catalytic inhibitors (aclarubicin, ICRF-187) to four distinct steps in the topoisomerase II catalytic cycle. Biochem Pharmacol. 1996 Apr 12;51(7):879-86.

Chemical & Physical Properties

Boiling Point897.7ºC at 760 mmHg
Melting Point151-153℃
Molecular FormulaC42H54ClNO15
Molecular Weight848.329
Flash Point496.7ºC
Exact Mass847.318176
PSA217.05000
LogP3.95970
InChIKeyKUSMIBXCRZTVML-PCCPLWKKSA-N
SMILESCCC1(O)CC(OC2CC(N(C)C)C(OC3CC(O)C(OC4CCC(=O)C(C)O4)C(C)O3)C(C)O2)c2c(cc3c(c2O)C(=O)c2c(O)cccc2C3=O)C1C(=O)OC.Cl
Storage condition2-8°C
Water SolubilitySoluble in DMSO or DMF at 25mg/ml

Safety Information

Hazard CodesT: Toxic;
Risk Phrases23/24/25
Safety Phrases36/37/39-45
RIDADRUN 3249
RTECSQI9283500
Packaging GroupII
Hazard Class6.1(a)

Synonyms

Aclarubicin HCl
Aclacin
1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-[(2R,6S)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl]-α-L-lyxo-hexopyra nosyl]-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy]-, methyl ester, (1R,2R,4S)-, hydrochloride (1:1)
Aclacinomycin A hydrochloride
Aclarubicin hydrochloride
methyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-O-{2,6-dideoxy-4-O-[(2R,6S)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl}-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate hydrochloride (1:1)
1-naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-[(2R,6S)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy]-, methyl ester, (1R,2R,4S)-, hydrochloride (1:1)
Methyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-4-O-{2,6-dideoxy-4-O-[(2R,6S)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl}-3-(dimethylamino)-α-L-lyx o-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydro-1-tetracenecarboxylate hydrochloride (1:1)
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