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P2076

Sigma-Aldrich

Polymyxin B nonapeptide hydrochloride

cationic cyclic peptide

Synonym(s):

PMBN

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About This Item

Empirical Formula (Hill Notation):
C43H74N14O11 · xHCl
Molecular Weight:
963.13 (free base basis)
MDL number:
MFCD00214217
UNSPSC Code:
12352209
PubChem Substance ID:
24898270
NACRES:
NA.26

Quality Level

200

form

lyophilized powder

color

white to light yellow

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

CC(C)CC1NC(=O)C(Cc2ccccc2)NC(=O)C(CCN)NC(=O)C(CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(CCN)NC1=O)C(C)O)NC(=O)C(CCN)NC(=O)C(N)C(C)O

InChI

1S/C43H74N14O11/c1-22(2)20-31-40(65)52-26(10-15-44)35(60)51-29(13-18-47)39(64)57-34(24(4)59)43(68)49-19-14-30(53-36(61)28(12-17-46)54-42(67)33(48)23(3)58)38(63)50-27(11-16-45)37(62)56-32(41(66)55-31)21-25-8-6-5-7-9-25/h5-9,22-24,26-34,58-59H,10-21,44-48H2,1-4H3,(H,49,68)(H,50,63)(H,51,60)(H,52,65)(H,53,61)(H,54,67)(H,55,66)(H,56,62)(H,57,64)

InChI key

PYHYGIPVYYRJHU-UHFFFAOYSA-N

Related Categories

Application

Polymyxin B nonapeptide hydrochloride has been used as an outer membrane permeabilizer, to characterize PAßN activity on membrane. It has been used as a control in antibacterial assays.

Biochem/physiol Actions

PMBN has endotoxin-neutralizing activity and thus can be utilized in adjunctive therapy against Gram-negative sepsis. It has been found that PMBN is less toxic than polymyxin B. Unlike polymyxin B, PMBN does not exhibit neurotoxicity and nephrotoxicity. While it retains the anti endotoxin property of the parent compound, it is much less potent.
Polymyxin B nonapeptide (PMBN), a cationic cyclic peptide derived from the antibacterial peptide polymyxin B, specifically increases the permeability of the outer membrane of Gram-negative bacteria toward hydrophobic antibiotics. PMBN has been used to evaluate multidrug efflux inhibitors in E. coli.
Polymyxin B nonapeptide hydrochloride is a derivative of PMB that induces outer membrane permeability in gram-negative bacteria.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents.
Vaara M
Antimicrobial Agents and Chemotherapy, 52(9), 3229-3236 (2008)
Evaluation of multidrug efflux pump inhibitors by a new method using microfluidic channels.
Matsumoto Y
PLoS ONE, 6(4), 1-12 (2011)
M Vaara et al.
Antimicrobial agents and chemotherapy, 24(1), 114-122 (1983-07-01)
The outer membrane-disorganizing effect of a short (10-min) treatment with polycationic agents was studied with smooth Salmonella typhimurium used as a test organism. The polycationic agents were the protamine salmine, a lysine polymer with 20 lysine residues (lysine20), and the
Jinshan Jin et al.
ChemMedChem, 11(22), 2511-2521 (2016-10-19)
With the widespread emergence of drug resistance, there is an urgent need to search for new antimicrobials, especially those against Gram-negative bacteria. Along this line, the identification of viable targets is a critical first step. The protein translocase SecA is
Haim Tsubery et al.
Molecular pharmacology, 62(5), 1036-1042 (2002-10-23)
Polymyxin B nonapeptide (PMBN), a cationic cyclic peptide derived from the antibacterial peptide polymyxin B, is capable of specifically increasing the permeability of the outer membrane (OM) of Gram-negative bacteria toward hydrophobic antibiotics. In this study, we evaluated the contribution
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