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C6830

Sigma-Aldrich

Cecropin A

≥97% (HPLC), powder

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$288.00
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0.1 MG
$288.00
0.5 MG
$1,090.00

About This Item

Fórmula empírica (notación de Hill):
C184H313N53O46
Número de CAS:
80451-04-3
Peso molecular:
4003.78
Número MDL:
MFCD00130752
Código UNSPSC:
12352202
NACRES:
NA.32

$288.00

Disponible para envío el14 de abril de 2025Detalles

Nivel de calidad

200

Ensayo

≥97% (HPLC)

Formulario

powder

espectro de actividad antibiótica

fungi
viruses

Modo de acción

cell membrane | interferes

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave 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

Descripción general

Cecropin A belongs to cecropin class[1] and comprises 37 amino acid residues in L configuration.[2] 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]

Aplicación

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[4]
  • to test its minimal inhibitory concentrations (MICs) in sensitivity assay for Photorhabdus variants[4]

Acciones bioquímicas o fisiológicas

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]

Otras notas

Lyophilized from 0.1% TFA in H2O

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000274419
0000274418
0000274419
0000274418
0000181867

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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
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
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
Yoon-Suk Alexander Chung et al.
The Journal of biological chemistry, 286(30), 26524-26532 (2011-05-27)
Non-opsonic phagocytosis is a primordial form of pathogen recognition that is mediated by the direct interaction of phagocytic receptors with microbial surfaces. In the fruit fly Drosophila melanogaster, the EGF-like repeat containing scavenger receptor Eater is expressed by phagocytes and
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
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