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B2809

Sigma-Aldrich

Bactenecin

≥95% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C63H118N24O13S2
Molecular Weight:
1483.89
MDL number:
MFCD00236810
UNSPSC Code:
51102829
PubChem Substance ID:
329773208
NACRES:
NA.85

Quality Level

200

Assay

≥95% (HPLC)

form

powder

solubility

1 mg/mL (in 1% TFA in H20)

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C(C)C)C(C)C)[C@@H](C)CC)C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCCNC(N)=N

InChI

1S/C63H118N24O13S2/c1-13-34(11)46-57(97)78-38(21-17-25-75-62(69)70)49(89)83-43(31(5)6)54(94)82-42(53(93)79-39(59(99)100)22-18-26-76-63(71)72)29-102-101-28-41(81-51(91)40(27-30(3)4)80-48(88)36(64)19-15-23-73-60(65)66)52(92)77-37(20-16-24-74-61(67)68)50(90)86-47(35(12)14-2)58(98)85-44(32(7)8)55(95)84-45(33(9)10)56(96)87-46/h30-47H,13-29,64H2,1-12H3,(H,77,92)(H,78,97)(H,79,93)(H,80,88)(H,81,91)(H,82,94)(H,83,89)(H,84,95)(H,85,98)(H,86,90)(H,87,96)(H,99,100)(H4,65,66,73)(H4,67,68,74)(H4,69,70,75)(H4,71,72,76)/t34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-/m0/s1

InChI key

RHISNKCGUDDGEG-CJMCYECYSA-N

Amino Acid Sequence

Arg-Leu-Cys-Arg-Ile-Val-Val-Ile-Arg-Val-Cys-Arg-OH (Disulfide bridge: 3-11)

General description

Chemical structure: peptide

Application

Bactenecin′s activity has been studied as a cyclic molecule as well as in a linear form. It was used to study the functional role of Trk1p in the mechanism of other antifungal peptides. It has been used to study chemokine and cytokine production, alteration of gene expression in host cells, and inhibition of proinflammatory responses of host cells to bacterial components.

Biochem/physiol Actions

Bactenecin is a 12-amino acid cationic antimicrobial peptide from bovine neutrophils. It strongly binds to LPS and perturbs the structure, fluidity and permeability of the inner membrane. This results in the leakage of cytosol and subsequent death of the bacteria.

Other Notes

Peptide antibiotic, originally isolated from bovine neutrophil granules
Keep container tightly closed in a dry and well-ventilated place.

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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D Romeo et al.
The Journal of biological chemistry, 263(20), 9573-9575 (1988-07-15)
Cytoplasmic granules of neutrophils store a variety of cationic polypeptides, which exert in vitro a potent antibacterial action and are potentially involved in host defense mechanisms. From an acid extract of bovine neutrophil granules we have purified over 2,000-fold a
B Gallis et al.
Biotechnology therapeutics, 1(4), 335-346 (1989-01-01)
Bactenecin is an antimicrobial peptide isolated from bovine neutrophils. Bactenecin was synthesized by solid-phase peptide synthesis and renatured to a fully disulfide bonded form. The peptide inhibits the growth of Escherichia coli and Staphylococcus aureus at the same concentration reported
Slavena Vylkova et al.
Antimicrobial agents and chemotherapy, 50(1), 324-331 (2005-12-27)
Salivary histatin 5 (Hst 5) kills the fungal pathogen Candida albicans via a multistep process which includes binding to Ssa1/2 proteins on the cell surface and requires the TRK1 potassium transporter. Hst 5-induced membrane permeability to propidium iodide (PI) was
Shirley M Halling et al.
Current microbiology, 56(3), 274-278 (2008-01-25)
Intracellular pathogens selected for increased susceptibility to polycations are commonly attenuated, yet the effect of decreased susceptibility to polycations on pathogenicity has not been researched. The polymyxin-resistant mutant Brucella abortus AJ100 was characterized by comparing its susceptibility to the polycationic
Dawn M E Bowdish et al.
Antimicrobial agents and chemotherapy, 49(5), 1727-1732 (2005-04-28)
Recent studies have demonstrated that in addition to their antimicrobial activity, cationic host defense peptides, like the human cathelicidin LL-37, perform many activities relating to innate immunity, including the induction or modulation of chemokine and cytokine production, alteration of gene
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