Chemical Structure
NAI-107 [Microbisporicin]
AG-CN2-0307
CAS Number845293-74-5
Product group Chemicals
Estimated Purity>80%
Molecular Weight2249.0 (A1; R=OH)2233.0 (A2; R=H)
Overview
- SupplierAdipoGen Life Sciences
- Product NameNAI-107 [Microbisporicin] [845293-74-5]
- Delivery Days Customer10
- CAS Number845293-74-5
- CertificationResearch Use Only
- Estimated Purity>80%
- Molecular FormulaC94H127ClN26O27S5 (A1) C94H127ClN26O26S5 (A2)
- Molecular Weight2249.0 (A1; R=OH)2233.0 (A2; R=H)
- Scientific DescriptionAntibacterial class I lantibiotic. Mixture of two similarly active and structurally related polypeptides (A1, 2246Da and A2, 2230Da) of 24 amino acids linked by 5 intramolecular thioether bridges. Inhibits cell wall synthesis and consequently bacterial growth by forming a complex with lipid intermediate II (Lipid II), a key intermediate in peptidoglycan biosynthesis. Efficiently interferes with late stages of cell wall biosynthesis leading to accumulation of the soluble peptidoglycan precursor UDP-N-acetylmuramic acid-pentapeptide (UDP-MurNAc-pentapeptide) in the cytoplasm. Active against aerobic and anaerobic Gram-positive pathogens, including all antibiotic-resistant strains (e.g. MRSA and VRE) in whole cell and in vitro assays as well as in vivo. Rapidly bactericidal and highly efficacious in experimental models of infection (septicemia, endocarditis, granuloma pouch) and developed for treatment of serious infections by multidrug-resistant Gram-positive bacteria. - Chemical. CAS: 845293-74-5 [A1/A2 Mixture]. Formula: C94H127ClN26O27S5 (A1), C94H127ClN26O26S5 (A2). MW: 2249.0 (A1; R=OH)2233.0 (A2; R=H). Isolated from Microbispora sp. Antibacterial class I lantibiotic. Mixture of two similarly active and structurally related polypeptides (A1, 2246Da and A2, 2230Da) of 24 amino acids linked by 5 intramolecular thioether bridges. Inhibits cell wall synthesis and consequently bacterial growth by forming a complex with lipid intermediate II (Lipid II), a key intermediate in peptidoglycan biosynthesis. Efficiently interfers with late stages of cell wall biosynthesis leading to accumulation of the soluble peptidoglycan precursor UDP-N-acetylmuramic acid-pentapeptide (UDP-MurNAc-pentapeptide) in the cytoplasm. Active against aerobic and anaerobic Gram-positive pathogens, including all antibiotic-resistant strains (e.g. MRSA and VRE) in whole cell and in vitro assays as well as in vivo. Rapidly bactericidal and highly efficacious in experimental models of infection (septicemia, endocarditis, granuloma pouch) and developed for treatment of serious infections by multiresistant Gram-positive bacteria.
- SMILESClC1=CC=C2C(C(C[C@@H]3NC([C@@H](CSC[C@H](NC([C@H](CC(C)C)NC(C(NC3=O)=C)=O)=O)C(N[C@@H]4C(N5[C@@](C(NCC(N[C@H](C(N[C@]([C@H](O)C)([H])C(N[C@H]6C(N7[C@@](C(NCC(NCC(NCC(N[C@@]8([H])C(N[C@@H](CC(N)=O)C(N[C@@](C(N[C@@]9([H])C(N[C@H](C(N[C@](CSC8)([H])C(N/C=C\SC9)=O)=O)CC%10=CC=CC=C%10)=O)=O)([H])CSC6)=O)=O)=O)=O)=O)=O)([H])C([H])C(O)C7)=O)=O)=O)CS[C@H]4C)=O)=O)([H])CCC5)=O)=O)NC(/C(NC([C@@H](N)C(C)C)=O)=C/C)=O)=O)=CN2)=C1
- Storage Instruction-20°C,2°C to 8°C
- UNSPSC12352200
References
- Determining the structure and mode of action of microbisporicin, a potent lantibiotic active against multiresistant pathogens: F. Castiglione, et al.; Chem. Biol. 15, 22 (2008)
- Efficacy of the new lantibiotic NAI-107 in experimental infections induced by multidrug-resistant Gram-positive pathogens: D. Jabes, et al.; Antimicrob. Agents Chemother. 55, 1671 (2011)
- Solution structure by nuclear magnetic resonance of the two lantibiotics 97518 and NAI-107: F. Vasile, et al.; J. Pept. Sci. 18, 129 (2012)
- Characterization of the congeners in the lantibiotic NAI-107 complex: S.I. Maffioli, et al.; J. Nat. Prod. 77, 79 (2014)
- The lantibiotic NAI-107 binds to bactoprenol-bound cell wall precursors and impairs membrane functions: D. Munch, et al.; J. Biol. Chem. 289, 12063 (2014)
- In vivo pharmacokinetics and pharmacodynamics of the lantibiotic NAI-107 in a neutropenic murine thigh infection model: A.J. Lepak, et al.; Antimicrob. Agents Chemother. 59, 1258 (2015)
- Family of class I lantibiotics from actinomycetes and improvement of their antibacterial activities: S.I. Maffioli, et al.; ACS Chem. Biol. 10, 1034 (2015)
- Advancing cell wall inhibitors towards clinical applications: S.I. Maffioli, et al.; J. Ind. Microbiol. Biotechnol. 43, 177 (2016) (Review)
- The Lantibiotic NAI-107 Efficiently Rescues Drosophila melanogaster from Infection with Methicillin-Resistant Staphylococcus aureus USA300: T.T. Thomsen, et al.; Antimicrob. Agents Chemother. 60, 5427 (2016)
- Expanding the potential of NAI-107 for treating serious ESKAPE pathogens: synergistic combinations against Gram-negatives and bactericidal activity against non-dividing cells: C. Brunati, et al.; J. Antimicrob. Chemother. 73, 414 (2018)