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ProductsBack/NAI-107 [Microbisporicin] [845293-74-5]
Chemical Structure
Chemical Structure
Chemical Structure

NAI-107 [Microbisporicin] [845293-74-5]

Research Use Only
AG-CN2-0307
AdipoGen Life Sciences
CAS Number845293-74-5
DownloadMSDS
Product group Chemicals
Estimated Purity>80%
Molecular Weight2249.0 (A1; R=OH)2233.0 (A2; R=H)
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    NAI-107 [Microbisporicin]
  • Delivery Days Customer
    10
  • CAS Number
    845293-74-5
  • Certification
    Research Use Only
  • Estimated Purity
    >80%
  • Molecular Formula
    C94H127ClN26O27S5 (A1) C94H127ClN26O26S5 (A2)
  • Molecular Weight
    2249.0 (A1; R=OH)2233.0 (A2; R=H)
  • Scientific Description
    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 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.
  • SMILES
    ClC1=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
  • UNSPSC
    12352200

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)