Macbecin

Macbecin belongs to the ansamycin family of antibiotics and was first isolated from actinomycete bacteria.[1][2] Macbecin possesses potent antitumor properties.

Macbecin I
Names
IUPAC name
(4E,6Z,8S,10E,12R,13S,14R,16S,17R)-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
Other names
Macbecin I
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
Properties
Chemical formula
C30H42N2O8
Molar mass 558.66308
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Macbecin II
Names
IUPAC name
(4E,6Z,8S,10E,12R,13S,14R,16S,17R)-20,22-dihydroxy-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,6,10,18,20-hexaen-9-yl carbamate
Other names
Macbecin II
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
Properties
Chemical formula
C30H44N2O8
Molar mass 560.67896
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Structure

Macbecin has an unusual macrocyclic lactam structure. There are two variants Macbecin I and II which correspond to the oxidized 1,4-benzoquinone and reduced hydroquinone respectively.

Mechanism of action

Macbecins mechanism of action is in part due to heat shock protein Hsp90 protein inhibition.[3]

References

  1. Tanida S, Hasegawa T, Higashide E (February 1980). "Macbecins I and II, new antitumor antibiotics. I. Producing organism, fermentation and antimicrobial activities". J. Antibiot. 33 (2): 199–204. doi:10.7164/antibiotics.33.199. PMID 7380729.
  2. Muroi M, Izawa M, Kosai Y, Asai M (February 1980). "Macbecins I and II, new antitumor antibiotics. II. Isolation and characterization". J. Antibiot. 33 (2): 205–12. doi:10.7164/antibiotics.33.205. PMID 7380730.
  3. Bohen SP (June 1998). "Genetic and Biochemical Analysis of p23 and Ansamycin Antibiotics in the Function of Hsp90-Dependent Signaling Proteins". Mol. Cell. Biol. 18 (6): 3330–9. doi:10.1128/MCB.18.6.3330. PMC 108914. PMID 9584173.
  • Macbecin+I at the US National Library of Medicine Medical Subject Headings (MeSH)
  • Macbecin+II at the US National Library of Medicine Medical Subject Headings (MeSH)


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