An anthracycline with antibiotic and anticancer activities
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Aclarubicin

Item No. 15993

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R,4S)-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-hexopyranosyl]-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy]-1-naphthacenecarboxylic acid, methyl ester
CAS Number
57576-44-0
Synonyms
  • NSC 208734
Molecular Formula
C42H53NO15
Formula Weight
811.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
230, 260, 433 nm
SMILES
O=C1C2=C(C(C3=CC=CC(O)=C31)=O)C=C(C4=C2O)[C@H]([C@](CC)(O)C[C@@H]4O[C@@]5(O[C@@H](C)[C@@H](O[C@]6([H])O[C@@H](C)[C@@H](O[C@@]7([H])CCC([C@H](C)O7)=O)[C@@H](O)C6)[C@@H](N(C)C)C5)[H])C(OC)=O
InChi Code
InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1
InChi Key
USZYSDMBJDPRIF-SVEJIMAYSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    100 µg

    $156

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    500 µg

    $692

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    Cayman Chemical
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    Product Description

    Aclarubicin is an anthracycline originally isolated from Streptomyces and has antibiotic and anticancer activities.1 It is active against B. subtilis, B. cereus, S. aureus, M. smegmatis, S. pyogenes, and S. faecalis (MICs = <0.2-2.5 μg/ml). Aclarubicin is a DNA intercalating agent, topoisomerase I poison, and an inhibitor of topoisomerase II catalytic activity.2,3 It inhibits the growth of L1210 leukemia cells (IC50 = 0.12 μg/ml) and increases survival in an L1210 murine leukemia model when administered at a dose of 1.5 mg/kg per day.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Oki, T., Matsuzawa, Y., Numata, K., et al. New antitumor antibiotics aclacinomycins A and B. J. Antibiot. (Tokyo) 28(10), 830-834 (1975).

    2. Nitiss, J.L., Pourquier, P., and Pommier, Y. Aclacinomycin A stabilizes topoisomerase I covalent complexes. Cancer Res. 57(20), 4564-4569 (1997).

    3. Hajji, N., Mateos, S., Pastor, N., et al. Induction of genotoxic and cytotoxic damage by aclarubicin, a dual topoisomerase inhibitor. Mutat. Res. 583(1), 26-35 (2005).