C6830

Cecropin A

Name: Cecropin A
Brand: SIGMA
Price: 21764.82 ZAR

≥97% (HPLC), powder

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0.5 MG

R 21,764.82

List PriceR 22,209.00

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About This Item

Empirical Formula (Hill Notation):

C₁₈₄H₃₁₃N₅₃O₄₆

CAS Number:

80451-04-3

Molecular Weight:

4003.78

UNSPSC Code:

12352202

NACRES:

NA.32

MDL number:

MFCD00130752

Key Documents

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Product Name

Cecropin A, ≥97% (HPLC), powder

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

assay

≥97% (HPLC)

form

powder

antibiotic activity spectrum

fungi
viruses

mode of action

cell membrane | interferes

storage temp.

−20°C

Quality Level

200

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Show Differences

1 of 4

This Item	C7927	30024	C1796
Sigma-Aldrich C6830 Cecropin A	Sigma-Aldrich C7927 Cecropin P1 Porcine	Sigma-Aldrich 30024 Cyclosporin A	Sigma-Aldrich C1796 Cecropin B
antibiotic activity spectrum fungi, viruses	antibiotic activity spectrum fungi	antibiotic activity spectrum fungi	antibiotic activity spectrum fungi
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
assay ≥97% (HPLC)	assay ≥95% (HPLC)	assay 97.0-101.5% (on dried basis)	assay ≥97% (HPLC)
form powder	form powder	form powder	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C
mode of action cell membrane \| interferes	mode of action cell membrane \| interferes	mode of action enzyme \| inhibits	mode of action cell membrane \| interferes

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[1]
in ultrasensitive radial diffusion assay against E coli to test Galleria mellonella protein 24 and apolipophorin III effects[2]
to test its minimal inhibitory concentrations (MICs) in sensitivity assay for Photorhabdus variants[2]

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.[1] The synthetic cecropin A in transgenic rice confers protection against bacterial as well as fungal pathogens.[3]

General description

Cecropin A belongs to cecropin class[1] and comprises 37 amino acid residues in L configuration.[4] Structurally, this peptide has a C-terminal hydrophobic α-helical structure and the amphipathic N-terminal end.[1] Cecropin A is linear and cationic in nature.[3]

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Production of cecropin A antimicrobial peptide in rice seed endosperm.

Mireia Bundó et al.

BMC plant biology, 14, 102-102 (2014-04-24)

Cecropin A is a natural antimicrobial peptide that exhibits rapid, potent and long-lasting lytic activity against a broad spectrum of pathogens, thus having great biotechnological potential. Here, we report a system for producing bioactive cecropin A in rice seeds. Transgenic

Modeling horizontal gene transfer (HGT) in the gut of the Chagas disease vector Rhodnius prolixus.

Scott Matthews et al.

Parasites & vectors, 4, 77-77 (2011-05-17)

Paratransgenesis is an approach to reducing arthropod vector competence using genetically modified symbionts. When applied to control of Chagas disease, the symbiont bacterium Rhodococcus rhodnii, resident in the gut lumen of the triatomine vector Rhodnius prolixus (Hemiptera: Reduviidae), is transformed

Antibacterial and antimembrane activities of cecropin A in Escherichia coli.

L Silvestro et al.

Antimicrobial agents and chemotherapy, 44(3), 602-607 (2000-02-19)

The ability of cecropin A to permeabilize and depolarize the membranes of Escherichia coli ML-35p bacteria has been compared to its bactericidal activity in an extension of earlier studies performed on synthetic lipid vesicle membranes (L. Silvestro, K. Gupta, J.

The role of NF-kappaB factor REL2 in the Aedes aegypti immune response.

Yevgeniya Antonova et al.

Insect biochemistry and molecular biology, 39(4), 303-314 (2009-06-26)

Mosquitoes transmit numerous diseases that continue to be an enormous burden on public health worldwide. Transgenic mosquitoes impervious to vector-borne pathogens, in concert with vector control and drug and vaccine development, comprise an arsenal of means anticipated to defeat mosquito-spread

The antimicrobial peptide cecropin A induces caspase-independent cell death in human promyelocytic leukemia cells.

José María Cerón et al.

Peptides, 31(8), 1494-1503 (2010-05-25)

Most antimicrobial peptides have been shown to have antitumoral activity. Cecropin A, a linear 37-residue antimicrobial polypeptide produced by the cecropia moth, has exhibited cytotoxicity in various human cancer cell lines and inhibitory effects on tumor growth. In this study

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