Macbecin

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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)
ChemSpider
  • I: InChI=1S/C30H42N2O8/c1-16-10-9-11-17(2)29(35)32-23-15-21(33)14-22(25(23)34)27(38-7)20(5)13-24(37-6)28(39-8)19(4)12-18(3)26(16)40-30(31)36/h9-12,14-16,19-20,24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b10-9-,17-11+,18-12+/t16-,19+,20-,24+,26?,27+,28-/m0/s1
    Key: PLTGBUPHJAKFMA-OEPVMNMSSA-N
  • II: InChI=1S/C30H44N2O8/c1-16-10-9-11-17(2)29(35)32-23-15-21(33)14-22(25(23)34)27(38-7)20(5)13-24(37-6)28(39-8)19(4)12-18(3)26(16)40-30(31)36/h9-12,14-16,19-20,24,26-28,33-34H,13H2,1-8H3,(H2,31,36)(H,32,35)/b10-9-,17-11+,18-12+/t16-,19+,20-,24+,26?,27+,28-/m0/s1
    Key: SVSFCSOFEPJFSF-OEPVMNMSSA-N
  • 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).
checkY verify (what is checkY☒N ?)
Close

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

External links

Related Articles

Wikiwand AI