Macbecin

Macbecins are a pair of chemical compounds in the ansamycin family of antibiotics. They are designated macbecin I and macbecin II and they were first isolated from actinomycete bacteria.[1][2] Macbecin possesses antitumor properties.[1] In vitro studies have shown that macbecins are effective in the eradication of Gram-positive bacteria, fungi, and protozoa including Tetrahymena pyriformis.[1]

Macbecins

Macbecin I

Macbecin II
Names
IUPAC names
I: (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
II: (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
Identifiers
3D model (JSmol)
  • I: C[C@H]1C[C@H]([C@H]([C@@H](/C=C(/C([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C=C([C@@H]1OC)C2=O)/C)C)OC(=O)N)\C)C)OC)OC
  • II: C[C@H]1C[C@H]([C@H]([C@@H](/C=C(/C([C@H](/C=C\C=C(\C(=O)NC2=CC(=CC(=C2O)[C@@H]1OC)O)/C)C)OC(=O)N)\C)C)OC)OC
Properties
I: C30H42N2O8
II: C30H44N2O8
Molar mass I: 558.66 g/mol
II: 560.68 g/mol
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

Structure

Macbecins have an unusual macrocyclic lactam structure. The two variants, macbecin I and II, correspond to the oxidized 1,4-benzoquinone and reduced hydroquinone, respectively.[2]

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.
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