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