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M7402

Sigma-Aldrich

Magainin II

≥97% (HPLC)

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Empirical Formula (Hill Notation):
C114H180N30O29S
CAS Number:
Molecular Weight:
2466.90
MDL number:
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)N[C@@H](CCCCN)C(=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](CC(N)=O)C(=O)N[C@@H](CO)C(O)=O

InChI

1S/C114H180N30O29S/c1-12-65(7)94(142-88(148)55-119)112(170)124-59-90(150)129-74(38-24-28-45-116)100(158)137-81(51-70-33-19-15-20-34-70)106(164)135-79(49-63(3)4)105(163)138-83(53-72-56-121-62-125-72)107(165)140-85(60-145)110(168)127-67(9)96(154)131-75(39-25-29-46-117)101(159)132-76(40-26-30-47-118)102(160)136-80(50-69-31-17-14-18-32-69)98(156)122-57-89(149)128-73(37-23-27-44-115)99(157)126-68(10)97(155)134-82(52-71-35-21-16-22-36-71)109(167)143-93(64(5)6)111(169)123-58-91(151)130-77(41-42-92(152)153)104(162)144-95(66(8)13-2)113(171)133-78(43-48-174-11)103(161)139-84(54-87(120)147)108(166)141-86(61-146)114(172)173/h14-22,31-36,56,62-68,73-86,93-95,145-146H,12-13,23-30,37-55,57-61,115-119H2,1-11H3,(H2,120,147)(H,121,125)(H,122,156)(H,123,169)(H,124,170)(H,126,157)(H,127,168)(H,128,149)(H,129,150)(H,130,151)(H,131,154)(H,132,159)(H,133,171)(H,134,155)(H,135,164)(H,136,160)(H,137,158)(H,138,163)(H,139,161)(H,140,165)(H,141,166)(H,142,148)(H,143,167)(H,144,162)(H,152,153)(H,172,173)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,93-,94-,95-/m0/s1

InChI key

MGIUUAHJVPPFEV-ABXDCCGRSA-N

Related Categories

Amino Acid Sequence

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

General description

Chemical structure: peptide
Magainin II is a member of the antimicrobial peptides family. It is a cationic peptide with Gly-Ile-Gly-Lys-Phe-Leu-His-Ser-Ala-Lys-Lys-Phe-Gly-Lys-Ala-Phe-Val-Gly-Glu-Ile-Met-Asn-Ser amino acid sequence. Magainin II is water soluble and non-hemolytic at its effective and amphiphilic antimicrobial concentrations.

Biochem/physiol Actions

Antibiotic peptide. Magainins are positively charged and amphiphatic. Thought to preferentially bind to anionic phospholipids abundant in bacterial membranes with the formation of dynamic peptide-lipid supramolecular pore and cell permeabilization. Binding to artificial neutral membranes has also been demonstrated.
Magainin II acts as an antibiotic in a variety of organisms. Magainin II exhibits cytotoxic and anti-proliferative effects via pore formation in bladder cancer cells. In mice, it acts as an anti-tumor agent in several cancer cell lines and tumors. Magainin II facilitates lactate dehydrogenase discharge from mammalian cells. It directly interacts with certain cell membranes via amphiphilic α-helix and forms permeable ion channels, which results in depolarization and irreversible cytolysis and finally cell death. At low concentrations, Magainin II retards the growth of bacterial and fungal species and it promotes cytolysis in protozoa.

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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