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Merck

M7152

Sigma-Aldrich

Magainin I

≥97% (HPLC)

Sinónimos:

GIGKFLHSAGKFGKAFVGEIMKS

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About This Item

Fórmula empírica (notación de Hill):
C112H177N29O28S
Número de CAS:
Peso molecular:
2409.85
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97% (HPLC)

antibiotic activity spectrum

fungi
viruses

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc3ccccc3)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc4ccccc4)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(O)=O

InChI

1S/C112H177N29O28S/c1-12-65(7)93(139-86(144)54-117)110(166)122-59-89(147)128-75(39-25-29-46-115)100(156)135-81(51-70-33-19-15-20-34-70)105(161)133-79(49-63(3)4)104(160)136-83(53-72-55-118-62-123-72)106(162)137-84(60-142)108(164)124-67(9)95(151)119-56-87(145)127-74(38-24-28-45-114)99(155)134-80(50-69-31-17-14-18-32-69)97(153)120-57-88(146)126-73(37-23-27-44-113)98(154)125-68(10)96(152)132-82(52-71-35-21-16-22-36-71)107(163)140-92(64(5)6)109(165)121-58-90(148)129-77(41-42-91(149)150)103(159)141-94(66(8)13-2)111(167)131-78(43-48-170-11)102(158)130-76(40-26-30-47-116)101(157)138-85(61-143)112(168)169/h14-22,31-36,55,62-68,73-85,92-94,142-143H,12-13,23-30,37-54,56-61,113-117H2,1-11H3,(H,118,123)(H,119,151)(H,120,153)(H,121,165)(H,122,166)(H,124,164)(H,125,154)(H,126,146)(H,127,145)(H,128,147)(H,129,148)(H,130,158)(H,131,167)(H,132,152)(H,133,161)(H,134,155)(H,135,156)(H,136,160)(H,137,162)(H,138,157)(H,139,144)(H,140,163)(H,141,159)(H,149,150)(H,168,169)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,92-,93-,94-/m0/s1

InChI key

OFIZOVDANLLTQD-ZVNXOKPXSA-N

Categorías relacionadas

Amino Acid Sequence

Gly-Ile-Gly-Lys-Phe-Leu-His-Ser-Ala-Gly-Lys-Phe-Gly-Lys-Ala-Phe-Val-Gly-Glu-Ile-Met-Lys-Ser

General description

Chemical structure: peptide

Application

Magainin I has been used in DNA binding assay. It has also been used to study its antimicrobial susceptibility.
Initial sites of magainin I binding to E. coli have been shown to be lipopolysaccharide.

Biochem/physiol Actions

Antibiotic peptide. Thought to preferentially bind to anionic phospholipids abundant in bacterial membranes with the formation of dynamic peptide-lipid supramolecular pore and cell permeabilization, magainins are positively charged and amphiphatic. Binding to artificial neutral membranes has also been demonstrated.
Magainin is a 23-residue peptide, and is naturally found on the skin of African clawed frog. It has a broad spectrum specificity towards many gram-negative bacteria. It has the ability to make transmembrane pores on the bacterial cell membrane, which leads to cell lysis. It is considered nontoxic to mammalian cells.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Biochemical enhancement of transdermal delivery with magainin peptide: modification of electrostatic interactions by changing pH
Kim YC, et al.
International Journal of Pharmaceutics, 362(1-2), 20-28 (2008)
Vincent Humblot et al.
Biomaterials, 30(21), 3503-3512 (2009-04-07)
An antibacterial peptide, Magainin I, was covalently bound to a mixed 11-mercaptoundecanoïc acid (MUA) and 6-mercaptohexanol (C6OH) (ratio 1:3) Self-Assembled Monolayer (SAM) on gold surfaces. Each step of the surface functionalization was characterized by Polarization Modulation Reflection Absorption InfraRed Spectroscopy
L H Vorland et al.
Scandinavian journal of infectious diseases, 31(5), 467-473 (1999-11-27)
We examined the initial binding sites of magainin 1, cecropin P1 and lactoferricin B in Staphylococcus aureus and Escherichia coli. All 3 peptides were active against E. coli, whereas only lactoferricin B exerted any activity against S. aureus. Soluble lipoteichoic
In-Vitro Susceptibility of Different Morphological Forms of Borrelia burgdorferi to Common Lyme Antibiotics in Combination with Antimicrobial Peptides
Eckard A and Wood S
Journal of microbiology & experimentation., 3(1-2) (2016)
F M Marassi et al.
Current opinion in structural biology, 8(5), 640-648 (1998-11-18)
The three-dimensional structures of membrane proteins are essential for understanding their functions, interactions and architectures. Their requirement for lipids has hampered structure determination by conventional approaches. With optimized samples, it is possible to apply solution NMR methods to small membrane

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