An antitumor antibiotic
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Gilvocarcin V

Item No. 14190

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(6-deoxy-α-D-galactofuranosyl)-8-ethenyl-1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one
CAS Number
77879-90-4
Synonyms
  • Anandimycin A
  • Antibiotic 1072B
  • DC-38-V
  • NSC 338943
  • NSC 348115
  • Toromycin A
Molecular Formula
C27H26O9
Formula Weight
494.5
Purity
≥98%
Formulation (Request formulation change)
A film
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C(O1)C2=C(C(OC)=CC(C=C)=C2)C3=C1C4=C([C@H]5O[C@@]([H])([C@H](O)C)[C@H](O)[C@H]5O)C=CC(O)=C4C(OC)=C3
InChi Code
InChI=1S/C27H26O9/c1-5-12-8-15-19(17(9-12)33-3)14-10-18(34-4)21-16(29)7-6-13(20(21)25(14)36-27(15)32)26-23(31)22(30)24(35-26)11(2)28/h5-11,22-24,26,28-31H,1H2,2-4H3/t11-,22-,23-,24+,26-/m1/s1
InChi Key
XCWHINLKQMCRON-UCDARZNSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Gilvocarcin V is an antitumor antibiotic with a coumarin-based aromatic structure that was originally isolated from the culture broth of S. gilvotanareus.1,2 It is strongly active against Gram-positive bacteria such as S. aureus and B. subtilis and efficacious against experimental tumors including sarcoma 180, Ehrlich carcinoma, Meth I fibrosarcoma, MH134 hepatoma, and lymphocytic leukemia P388.3 Gilvocarcin V inhibits DNA synthesis by promoting the selective cross-linking of both histone H3 and the heat shock protein, GRP78 to DNA when photoactivated by near-UV or visible light.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wei, T.T., Byrne, K.M., Warnick-Pickle, D., et al. Studies on the mechanism of action of gilvocarcin V and chrysomycin A. J. Antibiot. (Tokyo) 35(4), 545-548 (1982).

    2. Nakano, H., Matsuda, Y., Ito, K., et al. Gilvocarcins, new antitumor antibiotics. 1. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. (Tokyo) 34(3), 266-270 (1981).

    3. Morimoto, M., Okubo, S., Tomita, F., et al. Gilvocarcins, new antitumor antibiotics. 3. Antitumor activity. J. Antibiot. (Tokyo) 34(6), 701-707 (1981).

    4. 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).