75443-99-1

75443-99-1 structure

Name: Aclarubicin hydrochloride
Chemical Name: methyl (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
CAS Number: 75443-99-1
Molecular Formula: C₄₂H₅₄ClNO₁₅
Molecular Weight: 848.329
Catalog: API Antineoplastic agents Antibiotic antineoplastic agents
Create Date: 2018-06-20 10:23:28
Modify Date: 2024-01-05 21:07:13
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].

Name	methyl (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
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)

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.

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

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)

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