CAS 50935-71-2

Kirromicina

Descrizione:

Kirromicina è un composto antibiotico che appartiene alla classe dei macrolidi, noto specificamente per la sua attività contro alcuni ceppi batterici. È prodotto dal batterio *Micromonospora purpurea* e presenta un meccanismo d'azione unico inibendo la sintesi proteica nei batteri. Kirromicina si lega alla subunità ribosomiale, interferendo con il passaggio di traslocazione durante la traduzione, il che alla fine arresta la crescita batterica. Questo composto è caratterizzato dalla sua complessa struttura di macrolide, che include un grande anello di lattone e vari gruppi funzionali che contribuiscono alla sua attività biologica. Kirromicina è stato studiato per le sue potenziali applicazioni terapeutiche, in particolare nel trattamento di infezioni causate da batteri Gram-positivi. Tuttavia, il suo uso clinico è limitato a causa dello sviluppo di resistenza e della disponibilità di antibiotici più efficaci. Come molti antibiotici, la comprensione della farmacocinetica, tossicità e meccanismi di resistenza di Kirromicina continua a evolversi, rendendolo un argomento di interesse nella ricerca microbiologica e farmaceutica.

Formula: C₄₃H₆₀N₂O₁₂

InChI: InChI=1S/C43H60N2O12/c1-9-11-13-21-31-42(6,7)38(50)39(51)43(54,57-31)28(10-2)40(52)44-23-17-16-19-26(4)36(55-8)27(5)37-35(49)34(48)30(56-37)20-15-12-14-18-25(3)33(47)32-29(46)22-24-45-41(32)53/h9,11-22,24,27-28,30-31,34-39,48-51,54H,10,23H2,1-8H3,(H,44,52)(H2,45,46,53)/b11-9-,14-12+,17-16+,20-15+,21-13+,25-18+,26-19+/t27-,28-,30-,31+,34+,35+,36-,37+,38+,39-,43-/m1/s1

InChI key: InChIKey=HMSYAPGFKGSXAJ-PAHGNTJYSA-N

SMILES: [C@H](C(NC/C=C/C=C(/[C@H]([C@@H](C)[C@@]1(O[C@H](/C=C/C=C/C=C(/C(=O)C2=C(O)C=CNC2=O)\C)[C@H](O)[C@@H]1O)[H])OC)\C)=O)(CC)[C@@]3(O)O[C@@H](/C=C/C=C\C)C(C)(C)[C@@H](O)[C@H]3O

Sinonimi:

• (2R)-N-[(2E,4E,6R)-7-[(2S,5R)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(2-hydroxy-4-oxo-1H-pyridin-3-yl)-6-methyl-7-oxo-hepta-1,3,5-trienyl]tetrahydrofuran-2-yl]-6-methoxy-5-methyl-octa-2,4-dienyl]-2-[2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]tetrahydropyran-2-yl]butanamide
• (2S)-N-[(6S,7R)-7-{(2S,3S,4R,5R)-3,4-dihydroxy-5-[7-(2-hydroxy-4-oxo-1,4-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]tetrahydrofuran-2-yl}-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-[(2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-(penta-1,3-dien-1-yl)tetrahydro-2H-pyran-2-yl]butanamide (non-preferred name)
• (αS,2R,3R,4R,6S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-Dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-2H-pyran-2-acetamide
• 2H-Pyran-2-acetamide, N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-, (αS,2R,3R,4R,6S)-
• 2H-Pyran-2-acetamide, N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrienyl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadienyl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-1,3-pentadienyl]-, (αS,2R,3R,4R,6S)-
• 2H-Pyran-2-acetamide, N-[7-[5-[7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrienyl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadienyl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1,3-pentadienyl)-, [2R-[2α,2[S*[2E,4E,6S*,7R*[2S*,3S*,4R*,5R*(1E,3E,5E)]]],3β,4β,6β(1E,3E)]]-
• Delvomycin
• Kirromycin
• Mocimycin
• N-[(2E,4E)-7-{3,4-dihydroxy-5-[(1E,3E,5E)-7-(2-hydroxy-4-oxo-1,4-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]tetrahydrofuran-2-yl}-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-{2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dien-1-yl]tetrahydro-2H-pyran-2-yl}butanamide (non-preferred name)
• NSC 316094

Kirromycin

CAS: 50935-71-2

Formula: C₄₃H₆₀N₂O₁₂

Purezza: ≥ 96.0%

Colore e forma: Yellow powder

Peso molecolare: 796.94

Ref: 7W-GA9046

Kirromycin

CAS: 50935-71-2

Formula: C₄₃H₆₀N₂O₁₂

Peso molecolare: 796.96

Ref: 4Z-K-027001

Kirromycin from Streptomyces collinus

CAS: 50935-71-2

Kirromycin is a hydroxylated tetracycline antibiotic that inhibits protein synthesis. It is used as a chemotherapeutic treatment against microbial infections, and has been shown to be effective against Streptomyces collinus. Kirromycin is also an inhibitor of bacterial ribosome activity, which can lead to the death of bacteria. This compound binds to the 30S subunit of the ribosome and prevents the attachment of amino acids to the nascent polypeptide chain during protein synthesis. The antibiotic thiostrepton from Streptomyces collinus was found to inhibit both growth and antibiotic resistance in Saccharomyces cerevisiae strains.

Formula: C₄₃H₆₀N₂O₁₂

Purezza: Min. 95%

Peso molecolare: 796.94 g/mol

Ref: 3D-ACA93571