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Merck
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Principaux 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

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
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
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
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
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.
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