Need Assistance?

US & Canada:
+
UK: +

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Ceratotoxin A

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Ceratotoxin A is a peptide with 29 residues isolated from the accessory gland secretion fluid. It has strong antibacterial activity.

Category

Functional Peptides

Catalog number

BAT-009352

CAS number

150671-04-8

Molecular Formula

C135H243N35O32

Molecular Weight

2868.59

Specification
Reference Reading

IUPAC Name

(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S,3S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]hexanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]amino]propanoyl]amino]hexanoyl]amino]propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

Synonyms

Ser-Ile-Gly-Ser-Ala-Leu-Lys-Lys-Ala-Leu-Pro-Val-Ala-Lys-Lys-Ile-Gly-Lys-Ile-Ala-Leu-Pro-Ile-Ala-Lys-Ala-Ala-Leu-Pro; L-Proline, L-seryl-L-isoleucylglycyl-L-seryl-L-alanyl-L-leucyl-L-lysyl-L-lysyl-L-alanyl-L-leucyl-L-prolyl-L-valyl-L-alanyl-L-lysyl-L-lysyl-L-isoleucylglycyl-L-lysyl-L-isoleucyl-L-alanyl-L-leucyl-L-prolyl-L-isoleucyl-L-alanyl-L-lysyl-L-alanyl-L-alanyl-L-leucyl-

Appearance

White Lyophilized Powder

Purity

≥95% by HPLC

Density

1.2±0.1 g/cm3

Boiling Point

2450.8±65.0°C at 760 mmHg

Sequence

SIGSALKKALPVAKKIGKIALPIAKAALP

Storage

Store at -20°C

Solubility

Soluble in DMSO, Water

InChI

InChI=1S/C135H243N35O32/c1-26-76(15)105(164-116(182)87(142)69-171)127(193)144-68-103(174)153-98(70-172)124(190)148-82(21)112(178)159-94(63-71(5)6)123(189)158-92(49-34-40-58-140)120(186)156-90(47-32-38-56-138)118(184)147-83(22)114(180)160-95(64-72(7)8)132(198)168-60-42-51-99(168)125(191)163-104(75(13)14)129(195)149-84(23)110(176)155-91(48-33-39-57-139)119(185)157-93(50-35-41-59-141)122(188)165-106(77(16)27-2)128(194)143-67-102(173)152-88(45-30-36-54-136)121(187)166-107(78(17)28-3)130(196)151-86(25)115(181)161-96(65-73(9)10)133(199)169-61-43-52-100(169)126(192)167-108(79(18)29-4)131(197)150-85(24)111(177)154-89(46-31-37-55-137)117(183)146-80(19)109(175)145-81(20)113(179)162-97(66-74(11)12)134(200)170-62-44-53-101(170)135(201)202/h71-101,104-108,171-172H,26-70,136-142H2,1-25H3,(H,143,194)(H,144,193)(H,145,175)(H,146,183)(H,147,184)(H,148,190)(H,149,195)(H,150,197)(H,151,196)(H,152,173)(H,153,174)(H,154,177)(H,155,176)(H,156,186)(H,157,185)(H,158,189)(H,159,178)(H,160,180)(H,161,181)(H,162,179)(H,163,191)(H,164,182)(H,165,188)(H,166,187)(H,167,192)(H,201,202)/t76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,104-,105-,106-,107-,108-/m0/s1

InChI Key

KQXGJUOSTKVDEE-NWKXLRNUSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C)C(=O)NC(CCCCN)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)O)NC(=O)C2CCCN2C(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(C(C)CC)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(C(C)CC)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C3CCCN3C(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CO)NC(=O)CNC(=O)C(C(C)CC)NC(=O)C(CO)N

1. Susceptibility of Rickettsia monacensis and Rickettsia peacockii to Cecropin A, Ceratotoxin A, and lysozyme

Gerald D Baldridge, Timothy J Kurtti, Ulrike G Munderloh Curr Microbiol. 2005 Oct;51(4):233-8. doi: 10.1007/s00284-005-4532-7. Epub 2005 Aug 16.

Ticks host obligate intracellular bacteria that range from benign symbiotes to virulent human pathogens. The effects on those bacteria of antimicrobial peptides (AMPs) involved in arthropod innate immunity to microbial infections are largely unknown. We evaluated effects of AMPs and a c-type lysozyme on host cell-free suspensions of the tick symbiotes Rickettsia monacensis and Rickettsia peacockii with stain-based infectivity and viability assays. Cecropin A at a concentration of 8 muM: had a lethal effect on both rickettsiae while ceratotoxin A was approximately 20-fold less effective. Toxicity of both AMPs was synergized by lysozyme, an enzyme expressed by ticks. Lactoferrin, a transferrin, had no effect on R. monacensis at up to 110 microM. The rickettsiae were less sensitive to the AMPs than is typical of bacteria that grow extracellularly. Our assays may be useful in the study of AMP activity against other obligate intracellular bacteria.

2. The antibacterial peptide ceratotoxin A displays alamethicin-like behavior in lipid bilayers

Nathalie Saint, Laura Marri, Daniela Marchini, Gérard Molle Peptides. 2003 Nov;24(11):1779-84. doi: 10.1016/j.peptides.2003.09.015.

Ceratotoxin A (CtxA), a 36-residue alpha-helical cationic peptide isolated from the medfly Ceratitis capitata, exhibits strong antibacterial activity. To determine its mode of action against bacteria, we investigated the behavior of ceratotoxin A by incorporating it into planar lipid bilayers. Macroscopic and single channel conductance experiments showed that ceratotoxin A forms voltage-dependent ion channels in bilayers according to the barrel-stave model. The characteristics of the channel suggest that the C-terminal regions form bundles of five or six helices embedded in the membrane, such that the N-terminal moieties lie on the polar side of the lipid bilayer.

3. Targeting specific membranes with an azide derivative of the pore-forming peptide ceratotoxin A

Simon Finn Mayer, Julie Ducrey, Jessica Dupasquier, Laetitia Haeni, Barbara Rothen-Rutishauser, Jerry Yang, Aziz Fennouri, Michael Mayer Biochim Biophys Acta Biomembr. 2019 Oct 1;1861(10):183023. doi: 10.1016/j.bbamem.2019.07.011. Epub 2019 Jul 17.

Pore-forming antimicrobial peptides (AMPs) are attracting interest as cytolytic antibiotics and drug delivery agents with potential use for targeting cancer cells or multidrug-resistant pathogens. Ceratotoxin A (CtxA) is an insect-derived cytolytic AMP with 36 amino acids that is thought to protect the eggs of the medfly Ceratitis capitata against pathogens. Single channel recordings using planar lipid bilayers have shown that CtxA forms pores with well-defined conductance states resembling those of alamethicin; it also forms one of the largest pores among the group of ceratotoxins. In this work, we modified CtxA at its N-terminus with an azide group and investigated its pore-forming characteristics in planar lipid bilayer experiments. We demonstrate the possibility to target specific lipids by carrying out click reactions in-situ on lipid membranes that display a dibenzocyclooctyne (DBCO) moiety on their head group. As a result of covalent linkage of the peptides to the bilayer, pore-formation occurs at 10-fold reduced peptide concentration and with a reduced dependence on the transmembrane voltage compared to unlinked CtxA-azide peptides or native CtxA peptides.