Macbecin

chembox new
ImageFile = Macbecin_I.png ImageSize =
IUPACName = carbamic acid [(2R,3S,5R,6S,7R,8E,11S,12Z,14E)-2,5,6-trimethoxy-3,7,9,11,15-pentamethyl-16,20,22-trioxo-17-azabicyclo [16.3.1] docosa-1(21),8,12,14,18-pentaen-10-yl] ester
OtherNames = Macbecin I
Section1 = Chembox Identifiers
CASNo=73341-72-7
PubChem=5458728
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
Section2 = Chembox Properties
Formula=C₃₀H₄₂N₂O₈
MolarMass=558.66308 chembox new
ImageFile = Macbecin_II.png ImageSize =
IUPACName = carbamic acid [(2R,3S,5R,6S,7R,8E,11S,12Z,14E)-20,22-dihydroxy-2,5,6-trimethoxy-3,7,9,11,15-pentamethyl-16-oxo-17-azabicyclo [16.3.1] docosa-1(22),8,12,14,18,20-hexaen-10-yl] ester
OtherNames = Macbecin II
Section1 = Chembox Identifiers
CASNo=73341-73-8
PubChem=5458729
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
Section2 = Chembox Properties
Formula=C₃₀H₄₄N₂O₈
MolarMass=560.67896

Macbecin belongs to the ansamycin family of antibiotics and was first isolated from actinomycete bacteria.cite journal | author = Tanida S, Hasegawa T, Higashide E | title = Macbecins I and II, new antitumor antibiotics. I. Producing organism, fermentation and antimicrobial activities | journal = J. Antibiot. | volume = 33 | issue = 2 | pages = 199–204 | year = 1980 | month = February | pmid = 7380729 | doi = | url = | issn = ] cite journal | author = Muroi M, Izawa M, Kosai Y, Asai M | title = Macbecins I and II, new antitumor antibiotics. II. Isolation and characterization | journal = J. Antibiot. | volume = 33 | issue = 2 | pages = 205–12 | year = 1980 | month = February | pmid = 7380730 | doi = | url = | issn = ] Macbecin possesses potent antitumor properties.

tructure

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.cite journal | author = Bohen SP | title = Genetic and biochemical analysis of p23 and ansamycin antibiotics in the function of Hsp90-dependent signaling proteins | journal = Mol. Cell. Biol. | volume = 18 | issue = 6 | pages = 3330–9 | year = 1998 | month = June | pmid = 9584173 | pmc = 108914 | doi = | url = | issn = ]

References

External links

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