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P2076

Sigma-Aldrich

Polymyxin B nonapeptide hydrochloride

lyopholized powder

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

product name

Polymyxin B nonapeptide hydrochloride, cationic cyclic peptide

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

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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Hua-Ju Liang et al.
Archiv der Pharmazie, 353(3), e1900294-e1900294 (2020-01-03)
A series of (3-benzyl-5-hydroxyphenyl)carbamates were evaluated as new antibacterial agents. Several compounds showed potent inhibitory activity against sensitive and drug-resistant Gram-positive bacteria. The compounds are ineffective against all tested Gram-negative bacteria. The structure of the ester group exerted a profound
Mariana Castanheira et al.
International journal of antimicrobial agents, 56(1), 106011-106011 (2020-05-18)
This study examined ceftazidime-avibactam activity against carbapenem-resistant Enterobacterales (CRE) clinical isolates and resistance mechanisms among non-metallo β-lactamase (MBL) producers displaying ceftazidime-avibactam MIC values at 4 mg/L. CRE isolates (286 of 8161 Enterobacterales) collected in Asia-Pacific, Europe and Latin America during
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
Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents.
Vaara M
Antimicrobial Agents and Chemotherapy, 52(9), 3229-3236 (2008)
M Vaara
Microbiological reviews, 56(3), 395-411 (1992-09-01)
The outer membrane of gram-negative bacteria provides the cell with an effective permeability barrier against external noxious agents, including antibiotics, but is itself a target for antibacterial agents such as polycations and chelators. Both groups of agents weaken the molecular
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