Date published: 2025-10-18

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gamma-Rubromycin (CAS 27267-71-6)

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Alternate Names:
Methyl 4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxylate
CAS Number:
27267-71-6
Purity:
≥98%
Molecular Weight:
522.41
Molecular Formula:
C26H18O12
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Gamma-Rubromycin, a chemical compound isolated from the actinomycete Streptomyces collinus, is known for its complex interactions with DNA and RNA, making it a focus of biochemical research. This compound belongs to the rubromycin class of antibiotics, which are characterized by their unique tricyclic structure and a spiroketal ring system. Gamma-Rubromycin exerts its action primarily through the intercalation into DNA, where it inserts itself between the base pairs of the DNA helix. This insertion disrupts the normal double helix structure, which can inhibit the transcriptional processes by preventing RNA polymerase from effectively copying the DNA into RNA. Additionally, gamma-Rubromycin has been shown to inhibit reverse transcriptase enzymes, thereby affecting the replication of certain viruses and retrotransposons within cellular systems. In research settings, gamma-Rubromycin has been utilized to study its binding efficacy and specificity to nucleic acids, offering insights into the molecular dynamics of DNA-interacting agents. These studies are crucial for understanding how structural variations in molecules influence their interaction with biological macromolecules and can lead to the development of novel compounds for regulating genetic expression in experimental models.


gamma-Rubromycin (CAS 27267-71-6) References

  1. Use of a sonogashira-acetylide coupling strategy for the synthesis of the aromatic spiroketal skeleton of gamma-rubromycin.  |  Tsang, KY., et al. 2003. Org Lett. 5: 4425-7. PMID: 14602016
  2. Inhibition of human immunodeficiency virus-1 reverse transcriptase activity by rubromycins: competitive interaction at the template.primer site.  |  Goldman, ME., et al. 1990. Mol Pharmacol. 38: 20-5. PMID: 1695317
  3. Cleavage of four carbon-carbon bonds during biosynthesis of the griseorhodin a spiroketal pharmacophore.  |  Yunt, Z., et al. 2009. J Am Chem Soc. 131: 2297-305. PMID: 19175308
  4. Synthesis of (±)-γ-rubromycin via a new hypoiodite-catalytic oxidative cycloetherification.  |  Wei, L., et al. 2012. Org Lett. 14: 5302-5. PMID: 23050595
  5. Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp.  |  Harunari, E., et al. 2014. Mar Drugs. 12: 491-507. PMID: 24451191
  6. A convergent total synthesis of the telomerase inhibitor (±)-γ-rubromycin.  |  Wilsdorf, M. and Reissig, HU. 2014. Angew Chem Int Ed Engl. 53: 4332-6. PMID: 24623604
  7. Model Reactions for the Enantioselective Synthesis of γ-Rubromycin: Stereospecific Intramolecular Photoredox Cyclization of an ortho-Quinone Ether to a Spiroacetal.  |  Wakita, F., et al. 2018. Org Lett. 20: 3928-3932. PMID: 29932661
  8. Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces.  |  Wang, X., et al. 2019. J Nat Prod. 82: 3469-3476. PMID: 31833370
  9. Streptomyces iakyrus TA 36 as First-Reported Source of Quinone Antibiotic γ-Rubromycin.  |  Charousová, I., et al. 2023. Molecules. 28: PMID: 37630229
  10. [Rubromycins. 3. The constitution of alpha-rubromycin, beta-rubromycin, gamma-rubromycin, and gamma-iso-rubromycin].  |  Brockmann, H. and Zeeck, A. 1970. Chem Ber. 103: 1709-26. PMID: 5447178

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

gamma-Rubromycin, 1 mg

sc-364111
1 mg
$101.00

gamma-Rubromycin, 5 mg

sc-364111A
5 mg
$540.00