Macbecin

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Macbecin
Macbecin1.png
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
3D model (JSmol)
Properties
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
Macbecin2.png
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
3D model (JSmol)
Properties
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

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

Structure[edit]

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[edit]

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

References[edit]

  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. PMID 7380729. doi:10.7164/antibiotics.33.199. 
  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. PMID 7380730. doi:10.7164/antibiotics.33.205. 
  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. PMC 108914Freely accessible. PMID 9584173. 

External links[edit]