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AdipoGen Life Sciences

NAI-107 [Microbisporicin]

CHF 110.00
In stock
AG-CN2-0307-M0011 mgCHF 110.00
AG-CN2-0307-M0055 mgCHF 440.00
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Product Details
Synonyms Lantibiotic NAI 107; Lantibiotic 107891; MicrobisporicinA1/A2 Mixture (~75%:25%)
Product Type Chemical
Properties
Formula

C94H127ClN26O27S5 (A1)

C94H127ClN26O26S5 (A2)
MW 2249.0 (A1; R=OH)
2233.0 (A2; R=H)
CAS 845293-74-5 [A1/A2 Mixture]
Source/Host Chemicals Isolated from Microbispora sp.
Purity Chemicals ≥80% (HPLC, for A1/A2)
Appearance White to off-white powder.
Solubility Soluble in DMSO, aqueous acetonitrile or ethanol.
Identity Determined by 1H-NMR and MS.
Declaration Manufactured by Naicons Srl.
Other Product Data

Purity Note: The purity is referred exclusively to the main congener(s), the sample also contains minor related congeners. See: Characterization of the congeners in the lantibiotic NAI-107 complex: S.I. Maffioli, et al.; J. Nat. Prod. 77, 79 (2014)
InChi Key CEGKQFIOBQHXLN-YIWCYSMGSA-N
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
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Protect from light when in solution.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
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.

Product References

  1. 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)

  2. 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)

  3. Solution structure by nuclear magnetic resonance of the two lantibiotics 97518 and NAI-107: F. Vasile, et al.; J. Pept. Sci. 18, 129 (2012)

  4. Characterization of the congeners in the lantibiotic NAI-107 complex: S.I. Maffioli, et al.; J. Nat. Prod. 77, 79 (2014)

  5. 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)

  6. 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)

  7. Family of class I lantibiotics from actinomycetes and improvement of their antibacterial activities: S.I. Maffioli, et al.; ACS Chem. Biol. 10, 1034 (2015)

  8. Advancing cell wall inhibitors towards clinical applications: S.I. Maffioli, et al.; J. Ind. Microbiol. Biotechnol. 43, 177 (2016) (Review)

  9. 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)

  10. 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)

  11. Identification of a two-component regulatory system involved in antimicrobial peptide resistance in Streptococcus pneumoniae: A.M. Diagne, et al. PLoS Pathog. 18, e1010458 (2022)

  12. Microbisporicin (NAI-107) protects Galleria mellonella from infection with Neisseria gonorrhoeae: N. Hofkens, et al.; Microbiol. Spectr. ahead of print (2023)

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