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C6830

Sigma-Aldrich

Cecropin A

≥97% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C184H313N53O46
CAS Number:
80451-04-3
Molecular Weight:
4003.78
MDL number:
MFCD00130752
UNSPSC Code:
12352202
NACRES:
NA.32

Quality Level

200

assay

≥97% (HPLC)

form

powder

antibiotic activity spectrum

fungi
viruses

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

N4([C@@H](CCC4)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@H](CC)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N

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

InChI key

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

General description

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

Biochem/physiol Actions

Antibacterial peptide
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.

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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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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