An anthracycline with anticancer activity
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Nogalamycin

Item No. 27995

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,4R,5R,6R,11S,13S,14R)-11-[(6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-2,6-epoxy-2H-naphthaceno[1,2-b]oxocin-14-carboxylic acid, methyl ester
CAS Number
1404-15-5
Synonyms
  • NSC 70845
  • U 15167
Molecular Formula
C39H49NO16
Formula Weight
787.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: solubleMethanol: Soluble
SMILES
OC1=C(C(C(C(O)=CC2=C3O[C@@]4([H])[C@@H](O)[C@H](N(C)C)[C@@H](O)[C@@]2(O4)C)=C3C5=O)=O)C5=CC6=C1[C@@H](O[C@@]7([H])[C@H](OC)[C@@](OC)(C)[C@@H](OC)[C@H](C)O7)C[C@](C)(O)[C@@H]6C(OC)=O
InChi Code
InChI=1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3/t14-,19-,24-,25-,29-,31+,32-,33-,35+,36-,37-,38+,39+/m0/s1
InChi Key
KGTDRFCXGRULNK-JYOBTZKQSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $241

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    25 mg

    $838

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    Cayman Chemical
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    Product Description

    Nogalamycin is an anthracycline originally isolated from S. nogalater and a DNA-intercalating agent.1,2 It inhibits the DNA-unwinding and ATPase activities of P. falciparum DNA helicase 60 (IC50s = 2 and 0.5 μM, respectively) and the DNA cleavage activity of vaccinia virus topoisomerase (IC50 = 0.7 μM).3,4 Nogalamycin also inhibits the growth of MCF-7 and MDA-MB-231 human breast cancer cells (IC50s = 0.242 and 0.37 μM, respectively).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Torkkell, S., Kunnari, T., Palmu, K., et al. Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater. Antimicrob. Agents Chemother. 44(2), 396-399 (2000).

    2. Neidle, S., Pearl, L.H., and Skelly, J.V. DNA structure and perturbation by drug binding. Biochem. J. 243(1), 1-13 (1987).

    3. Pradhan, A., and Tuteja, R. Plasmodium falciparum DNA helicase 60. dsRNA- and antibody-mediated inhibition of malaria parasite growth and downregulation of its enzyme activities by DNA-interacting compounds. FEBS J. 273(15), 3545-3556 (2006).

    4. Yakovleva, L., Handy, C.J., Sayer, J.M., et al. Benzo[c]phenanthrene adducts and nogalamycin inhibit DNA transesterification by vaccinia topoisomerase. The Journal of Biological Chemisty 279(22), 23335-23342 (2004).

    5. Dasgupta, H., Islam, M.S., Alam, N., et al. Induction of HRR genes and inhibition of DNMT1 is associated with anthracycline anti-tumor antibiotic-tolerant breast carcinoma cells. Mol. Cell Biochem. 453(1-2), 163-178 (2019).