Gilvocarcin V A metabolite that displays potent antibacterial, antifungal and antiviral activity

Gilvocarcin V (CAS 77879-90-4)

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Application: A metabolite that displays potent antibacterial, antifungal and antiviral activity
CAS Number: 77879-90-4
Purity: >95%
Molecular Weight: 494.5
Molecular Formula: C27H26O9
* Refer to Certificate of Analysis for lot specific data (including water content).
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Gilvocarcin V is the major analogue of a complex of C-glycoside antitumor actives isolated from a Streptomyces sp. Gilvocarcin V contains a vinyl group in the 8-position and is the most potent analogue of the complex. It is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. The metabolite displays potent antibacterial, antifungal, antiviral and antitumor activity. Recent research on the gilvocarcins suggests that they act as photoactivated crosslinkers of DNA to histones. Gilvocarcin V has also been shown to be cytotoxic against Gram-positive bacteria. Mediates a unique cross-linking reaction between DNA and histidine H3. And is shown to be weakly active against Gram-negative bacteria, fungi and tumors. Also an antineoplastic and a photosensitizing compound.


References

1. Balitz, D.M., et al. 1981. J. Antibiot. 34: 1544-1555. PMID: 7344705
2. Nakano, H., et al. 1981. J. Antibiot. 34: 266-270. PMID: 7275807
3. Elespuru, R.K., et al. 1984. Science. 223: 69-71. PMID: 6229029
4. Peak, M.J., et al. 1988. Chem. Biol. Interact. 67: 267-274. PMID: 3191537
5. Lorico, A., et al. 1993. Eur. J. Cancer. 29A: 1985-1991. PMID: 8280493
6. Matsumoto, A., et al. 1994. Photochem. Photobiol. 60: 225-230. PMID: 7972373
7. Oyola, R., et al. 1997. Photochem. Photobiol. 65: 802-810. PMID: 9155255
8. Matsumoto, A., et al. 2000. Cancer Res. 60: 3921-3926. PMID: 10919670

Appearance :
Crystalline
Physical State :
Solid
Derived From :
Streptomyces sp.
Solubility :
Soluble in DMSO, DMF (moderately), methanol (moderately), ethanol (moderately), and water (poor).
Storage :
Store at -20° C
Melting Point :
322.54° C (Predicted)
Boiling Point :
821.61° C at 760 mmHg (Predicted)
Density :
1.45 g/cm3 (Predicted)
Refractive Index :
n20D 1.70 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
DI2240000
PubChem CID :
11027418
SMILES :
CC(C1C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=CC(=CC(=C54)OC)C=C)OC)O)O)O

Download SDS (MSDS)

Certificate of Analysis

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