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Key Documents

C6830

Sigma-Aldrich

Cecropin A

≥97% (HPLC), powder

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About This Item

Formule empirique (notation de Hill):
C184H313N53O46
Numéro CAS:
80451-04-3
Poids moléculaire :
4003.78
Numéro MDL:
MFCD00130752
Code UNSPSC :
12352202
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

powder

Spectre d'activité de l'antibiotique

fungi
viruses

Mode d’action

cell membrane | interferes

Température de stockage

−20°C

InChI

1S/C184H313N53O46/c1-27-98(16)145(182(282)235-149(102(20)31-5)181(281)218-115(59-39-46-76-187)159(259)206-103(21)152(252)205-92-138(246)237-82-52-65-130(237)173(273)208-106(24)154(254)228-143(96(12)13)176(276)209-107(25)155(255)229-144(97(14)15)177(277)231-142(95(10)11)175(275)204-89-135(243)211-121(66-70-131(193)239)160(260)207-105(23)156(256)236-150(108(26)238)183(283)221-123(68-72-133(195)241)168(268)232-146(99(17)28-2)178(278)210-104(22)153(253)213-114(151(197)251)58-38-45-75-186)227-137(245)91-202-158(258)129(87-140(249)250)226-163(263)120(64-51-81-200-184(198)199)219-179(279)148(101(19)30-4)234-172(272)128(86-134(196)242)225-164(264)122(67-71-132(194)240)212-136(244)90-203-174(274)141(94(8)9)230-166(266)118(62-42-49-79-190)215-165(265)124(69-73-139(247)248)220-180(280)147(100(18)29-3)233-167(267)119(63-43-50-80-191)214-161(261)116(60-40-47-77-188)216-170(270)126(84-109-53-33-32-34-54-109)224-169(269)125(83-93(6)7)223-162(262)117(61-41-48-78-189)217-171(271)127(222-157(257)112(192)56-37-44-74-185)85-110-88-201-113-57-36-35-55-111(110)113/h32-36,53-55,57,88,93-108,112,114-130,141-150,201,238H,27-31,37-52,56,58-87,89-92,185-192H2,1-26H3,(H2,193,239)(H2,194,240)(H2,195,241)(H2,196,242)(H2,197,251)(H,202,258)(H,203,274)(H,204,275)(H,205,252)(H,206,259)(H,207,260)(H,208,273)(H,209,276)(H,210,278)(H,211,243)(H,212,244)(H,213,253)(H,214,261)(H,215,265)(H,216,270)(H,217,271)(H,218,281)(H,219,279)(H,220,280)(H,221,283)(H,222,257)(H,223,262)(H,224,269)(H,225,264)(H,226,263)(H,227,245)(H,228,254)(H,229,255)(H,230,266)(H,231,277)(H,232,268)(H,233,267)(H,234,272)(H,235,282)(H,236,256)(H,247,248)(H,249,250)(H4,198,199,200)/t98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108+,112-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-/m0/s1

Clé InChI

HCQPHKMLKXOJSR-IRCPFGJUSA-N

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Amino Acid Sequence

Lys-Trp-Lys-Leu-Phe-Lys-Lys-Ile-Glu-Lys-Val-Gly-Gln-Asn-Ile-Arg-Asp-Gly-Ile-Ile-Lys-Ala-Gly-Pro-Ala-Val-Ala-Val-Val-Gly-Gln-Ala-Thr-Gln-Ile-Ala-Lys-NH2

Description générale

Cecropin A belongs to cecropin class and comprises 37 amino acid residues in L configuration. Structurally, this peptide has a C-terminal hydrophobic α-helical structure and the amphipathic N-terminal end. Cecropin A is linear and cationic in nature.

Application

Cecropin A has been used as an antimicrobial peptide (AMP):
  • to test its cytotoxic effect on breast adenocarcinoma (MDA-MB-231) and human mesothelioma (M14K) cell lines
  • in ultrasensitive radial diffusion assay against E coli to test Galleria mellonella protein 24 and apolipophorin III effects
  • to test its minimal inhibitory concentrations (MICs) in sensitivity assay for Photorhabdus variants

Actions biochimiques/physiologiques

Antibacterial peptide originally identified in moths (Hyalophora cecropia) and later in pig intestine.
Cecropin A interacts with cell membranes and makes it permeable for electrolytes. Cecropin A thus, favors cytolysis and finally cell death in the hepatocellular carcinoma and lymphoma. The synthetic cecropin A in transgenic rice confers protection against bacterial as well as fungal pathogens.

Autres remarques

Lyophilized from 0.1% TFA in H2O

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Xiuqing Wang et al.
Experimental biology and medicine (Maywood, N.J.), 237(3), 312-317 (2012-03-02)
The hybrid peptide CA(1-7)-M(2-12) gene was designed according to the N-terminal 1-7 amino acid sequence of the antimicrobial peptide cecropin A (CA) and the N-terminal 2-12 amino acid sequence of maganin (M) and synthesized using Pichia pastoris preferred codons. The
Sequence and specificity of two antibacterial proteins involved in insect immunity. Nature 292: 246-248. 1981.
Håkan Steiner et al.
Journal of immunology (Baltimore, Md. : 1950), 182(11), 6635-6637 (2009-05-21)
Sichen Shao et al.
Cell, 147(7), 1576-1588 (2011-12-27)
Metazoans secrete an extensive array of small proteins essential for intercellular communication, defense, and physiologic regulation. Their synthesis takes mere seconds, leaving minimal time for recognition by the machinery for cotranslational protein translocation into the ER. The pathway taken by
Loredana Mereuta et al.
Langmuir : the ACS journal of surfaces and colloids, 28(49), 17079-17091 (2012-11-13)
Metal ions binding exert a crucial influence upon the aggregation properties and stability of peptides, and the propensity of folding in various substates. Herein, we demonstrate the use of the α-HL protein as a powerful nanoscopic tool to probe Cu(2+)-triggered
Fatima Cairrao et al.
Molecular and cellular biology, 29(10), 2636-2643 (2009-03-11)
In mammals, AU-rich elements (AREs) are critical regulators of mRNA turnover. They recruit ARE-binding proteins that inhibit or stimulate rapid mRNA degradation in response to stress or developmental cues. Using a bioinformatics approach, we have identified AREs in Drosophila melanogaster
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