An antibiotic with antitumor properties
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Chrysomycin B

Item No. 14189

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(6-deoxy-3-C-methyl-β-gulopyranosyl)-1-hydroxy-10,12-dimethoxy-8-methyl-6H-benzo[d]naphtho[1,2-b]pyran-6-one
CAS Number
83852-56-6
Synonyms
  • Albacarcin M
  • Virenomycin M
Molecular Formula
C27H28O9
Formula Weight
496.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Slightly SolubleMethanol: Slightly Soluble
SMILES
O=C(O1)C2=C(C(OC)=CC(C)=C2)C3=C1C4=C(C5OC(C)C(O)C(C)(O)C5O)C=CC(O)=C4C(OC)=C3
InChi Code
InChI=1S/C27H28O9/c1-11-8-15-19(17(9-11)33-4)14-10-18(34-5)21-16(28)7-6-13(20(21)22(14)36-26(15)31)23-25(30)27(3,32)24(29)12(2)35-23/h6-10,12,23-25,28-30,32H,1-5H3
InChi Key
BJPYMDSMDBCKEP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    250 µg

    $183

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    1 mg

    $435

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    Cayman Chemical
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    Product Description

    Chrysomycin B is an antibiotic isolated from a strain of Streptomyces.1 It differs from its analog chrysomycin A (Item No. 14188)2,3 by having a methyl, rather than vinyl, group in the 8-position of the chromophore. Like its analog, chrysomycin B suppresses the growth of transplantable tumors in mice, an effect that may be related to its ability to bind DNA.3,4,5 It also causes DNA damage in the human lung adenocarcinoma A549 cell line and inhibits topoisomerase II.5 Chrysomycin B is structurally very similar to gilvocarcin V, which promotes DNA cross-linking with histone 3 and GRP78 when photoactivated by near-UV light.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Strelitz, F., Flon, H., and Asheshov, I.N. Chrysomycin: A new antibiotic substance for bacterial viruses. J. Bacteriol. 69(3), 280-283 (1955).

    2. Weiss, U., Yoshihira, K., Highet, R.J., et al. The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A. J. Antibiot. (Tokyo) 35(9), 1194-1201 (1982).

    3. Matson, J.A., Rose, W.C., Bush, J.A., et al. Antitumor activity of chrysomycins M and V. J. Antibiot. (Tokyo) 42(9), 1446-1448 (1989).

    4. Burres, N.S., Frigo, A., Rasmussen, R.R., et al. A colorimetric microassay for the detection of agents that interact with DNA. J. Nat. Prod. 55(11), 1582-1587 (1992).

    5. Lorico, A., and Long, B.H. Biochemical characterisation of elsamicin and other coumarin-related antitumour agents as potent inhibitors of human topoisomerase II. Eur. J. Cancer 29A(14), 1985-1991 (1993).

    6. Matsumoto, A., and Hanawalt, P.C. Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts. Cancer Res. 60(14), 3921-3926 (2000).