Macbecin: Difference between revisions

| verifiedrevid = 387419429

| ImageFile = Macbecin1.png

| ImageSize =

| IUPACName = (4''E'',6''Z'',8''S'',10''E'',12''R'',13''S'',14''R'',16''S'',17''R'')-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

| OtherNames = Macbecin I

| 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

| C=30 | H = 42 | N=2 | O= 8

| MolarMass=558.66308

{{chembox

| ImageFile = Macbecin2.png

| ImageSize =

| IUPACName = (4''E'',6''Z'',8''S'',10''E'',12''R'',13''S'',14''R'',16''S'',17''R'')-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

| 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

| C=30 | H = 44 | N=2 | O= 8

| MolarMass=560.67896

}}

}}

'''Macbecin''' belongs to the [[ansamycin]] family of [[antibiotic]]s and was first isolated from [[actinomycete]] bacteria.<ref name="pmid7380729">{{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 = }}</ref><ref name="pmid7380730">{{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 = }}</ref> Macbecin possesses potent [[chemotherapy|antitumor]] properties.

Macbecin has an unusual [[macrocycle|macrocyclic]] [[lactam]] structure. There are two variants Macbecin I and II which correspond to the oxidized [[1,4-benzoquinone]] and reduced [[hydroquinone]] respectively.

Macbecins mechanism of action is in part due to [[heat shock protein]] [[Hsp90]] protein inhibition.<ref name="pmid9584173">{{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 = }}</ref>

[[Category:Antibiotics]]

[[Category:Quinones]]

{{Pharma-stub}}