NAI-107 [Microbisporicin]
Product Code: AG-CN2-0307
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0307-M001 | 1 mg | £90.00 |
Quantity:
| AG-CN2-0307-M005 | 5 mg | £330.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Lantibiotic NAI 107; Lantibiotic 107891; MicrobisporicinA1/A2 Mixture (~75%:25%)
Appearance:
White to off-white powder.
CAS:
845293-74-5 [A1/A2 Mixture]
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light.Protect from light when in solution.
InChi:
InChI=1S/C94H127ClN26O26S5/c1-9-52(107-91(144)73(97)43(4)5)78(131)113-61-37-150-39-63(115-80(133)54(22-42(2)3)108-76(129)44(6)104-79(132)56(110-85(61)138)24-48-28-99-53-18-17-49(95)25-51(48)53)87(140)119-75-46(8)152-41-64(106-72(128)32-103-89(142)66-16-13-20-120(66)94(75)147)88(141)118-74(45(7)122)92(145)117-65-40-151-38-62-86(139)116-60-34-148-21-19-98-77(130)58(112-81(134)55(109-84(60)137)23-47-14-11-10-12-15-47)35-149-36-59(83(136)111-57(27-68(96)124)82(135)114-62)105-71(127)31-101-69(125)29-100-70(126)30-102-90(143)67-26-50(123)33-121(67)93(65)146/h9-12,14-15,17-19,21,25,28,42-43,45-46,50,54-67,73-75,99,122-123H,6,13,16,20,22-24,26-27,29-41,97H2,1-5,7-8H3,(H2,96,124)(H,98,130)(H,100,126)(H,101,125)(H,102,143)(H,103,142)(H,104,132)(H,105,127)(H,106,128)(H,107,144)(H,108,129)(H,109,137)(H,110,138)(H,111,136)(H,112,134)(H,113,131)(H,114,135)(H,115,133)(H,116,139)(H,117,145)(H,118,141)(H,119,140)/b21-19-,52-9-/t45-,46+,50?,54+,55+,56+,57+,58+,59-,60-,61-,62+,63+,64+,65-,66+,67+,73+,74+,75+/m1/s1
InChiKey:
CEGKQFIOBQHXLN-YIWCYSMGSA-N
Long Description:
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.
Molecular Formula:
C94H127ClN26O27S5 (A1)
C94H127ClN26O26S5 (A2)
Molecular Weight:
2249.0 (A1; R=OH)2233.0 (A2; R=H)
Other 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)
Package Type:
Vial
Product 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.
Purity:
>80% (HPLC, for A1/A2)
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=CSC9)=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
Solubility Chemicals:
Soluble in DMSO, aqueous acetonitrile or ethanol.
Source / Host:
Isolated from Microbispora sp.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
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)
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