Date published: 2025-12-5

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Gilvocarcin M (CAS 77879-89-1)

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Application:
Gilvocarcin M is The minor analogue of Gilvocarcin V with anti-bact, -fungal, -viral and -tumor activity
CAS Number:
77879-89-1
Purity:
95%
Molecular Weight:
482.5
Molecular Formula:
C26H26O9
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Gilvocarcin M is a complex natural product belonging to the gilvocarcin group of antibiotics, originally isolated from the bacterium Streptomyces griseoflavus. Structurally characterized by a chromophore linked to a glycosidic moiety, gilvocarcin M exhibits a notable mode of action primarily through the formation of a covalent adduct with DNA upon activation by light. Specifically, under UV irradiation, gilvocarcin M generates reactive oxygen species and binds to the guanine bases of DNA, thereby interfering with DNA replication and transcription processes. This interaction not only inhibits the growth of cells by blocking genetic material replication but also has been shown to cross-link DNA to associated proteins, further disrupting cellular functions. In research, gilvocarcin M has been extensively used to study the photochemical properties of drug-DNA interactions, offering insights into the dynamics of photo-induced cytotoxicity. These studies are crucial for understanding how light-activated compounds can be used to manipulate biological processes at the molecular level, including the design of photo-responsive drugs. Additionally, research on gilvocarcin M has contributed to broader discussions in the fields of chemical biology and photopharmacology, particularly in how natural products can be engineered to enhance their efficacy and selectivity as potential tools for controlling biological pathways in a light-dependent manner.


Gilvocarcin M (CAS 77879-89-1) References

  1. Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts.  |  Matsumoto, A. and Hanawalt, PC. 2000. Cancer Res. 60: 3921-6. PMID: 10919670
  2. Model studies towards the synthesis of gilvocarcin M.  |  Cordero-Vargas, A., et al. 2005. Org Biomol Chem. 3: 4432-43. PMID: 16327904
  3. Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.  |  Tibrewal, N., et al. 2012. J Am Chem Soc. 134: 18181-4. PMID: 23102024
  4. Activation of antitumor agent gilvocarcins by visible light.  |  Elespuru, RK. and Gonda, SK. 1984. Science. 223: 69-71. PMID: 6229029
  5. Gilvocarcins, new antitumor antibiotics. 4. Mode of action.  |  Tomita, F., et al. 1982. J Antibiot (Tokyo). 35: 1038-41. PMID: 6815145
  6. The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A.  |  Weiss, U., et al. 1982. J Antibiot (Tokyo). 35: 1194-201. PMID: 7142022
  7. Gilvocarcins, new antitumor antibiotics. 1. Taxonomy, fermentation, isolation and biological activities.  |  Nakano, H., et al. 1981. J Antibiot (Tokyo). 34: 266-70. PMID: 7275807
  8. Gilvocarcins, new antitumor antibiotics. 2. Structural elucidation.  |  Takahashi, K., et al. 1981. J Antibiot (Tokyo). 34: 271-5. PMID: 7275808
  9. Antitumor agents from Streptomyces anandii: gilvocarcins V, M and E.  |  Balitz, DM., et al. 1981. J Antibiot (Tokyo). 34: 1544-55. PMID: 7344705
  10. Photophysical properties of gilvocarcins V and M and their binding constant to calf thymus DNA.  |  Oyola, R., et al. 1997. Photochem Photobiol. 65: 802-10. PMID: 9155255

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Gilvocarcin M, 500 µg

sc-202169
500 µg
$359.00