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Aclarubicin hydrochloride

Names

[ CAS No. ]:
75443-99-1

[ Name ]:
Aclarubicin hydrochloride

[Synonym ]:
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)

Biological Activity

[Description]:

Aclacinomycin 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 Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Others

[In Vitro]

Aclacinomycin 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 Point ]:
897.7ºC at 760 mmHg

[ Melting Point ]:
151-153℃

[ Molecular Formula ]:
C42H54ClNO15

[ Molecular Weight ]:
848.329

[ Flash Point ]:
496.7ºC

[ Exact Mass ]:
847.318176

[ PSA ]:
217.05000

[ LogP ]:
3.95970

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Soluble in DMSO or DMF at 25mg/ml

Safety Information

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
UN 3249

[ RTECS ]:
QI9283500

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Related Compounds