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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
Número MDL:
Código UNSPSC:
12352202
ID de la sustancia en PubChem:
NACRES:
NA.32

Nivel de calidad

Análisis

≥97% (HPLC)

espectro de actividad antibiótica

fungi
viruses

Modo de acción

cell membrane | interferes

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

OFIZOVDANLLTQD-ZVNXOKPXSA-N

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

Descripción general

Chemical structure: peptide

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Otras notas

Lyophilized from 0.1% TFA in H2O

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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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)
Sam Maher et al.
Biochemical pharmacology, 71(9), 1289-1298 (2006-03-15)
Antimicrobial peptides (AMPs) are a diverse group of proteinaceous compounds ranging in size, complexity and antimicrobial spectrum. The activity of AMPs against gut pathogens warrants the study of the interaction of AMPs with the mammalian gastrointestinal tract. In particular, the
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

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