Macbecin

Macbecin belongs to the ansamycin family of antibiotics and was first isolated from actinomycete bacteria.[1][2] Macbecin possesses potent antitumor properties. In-vitro studies have shown that Macbecin is effective in the eradication of Gram-positive bacteria, fungi, and protozoa including Tetrahymena pyriformis.[1]

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
SMILES
  • CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C=C(C1OC)C2=O)C)C)OC(=O)N)C)C)OC)OC
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
SMILES
  • CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=C(C(=CC(=C2)O)C1OC)O)C)C)OC(=O)N)C)C)OC)OC
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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