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Crotamine

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

Crotonamine is a potassium channel inhibitor.

Category

Peptide Inhibitors

Catalog number

BAT-009114

CAS number

58740-15-1

Molecular Formula

C214H326N64O54S7

Molecular Weight

4883.73

Specification
Reference Reading

IUPAC Name

3-[(1R,2aS,4S,5aS,8aS,10S,15aR,16S,19S,22S,25S,28S,34S,37S,40S,43R,46S,49S,52S,55S,58S,61R,66R,69S,72S,75S,84S,87R,90S,96S,99S)-66-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-15a-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[2-[[(2S)-1-(carboxymethylamino)-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]carbamoyl]-5a,34,58,72,75,99-hexakis(4-aminobutyl)-28,90-dibenzyl-8a-[(2S)-butan-2-yl]-46,52-bis(3-carbamimidamidopropyl)-25,40-bis(carboxymethyl)-19,22-bis(hydroxymethyl)-69,84-bis(1H-imidazol-5-ylmethyl)-49,55-bis(1H-indol-3-ylmethyl)-4-(2-methylpropyl)-37-(2-methylsulfanylethyl)-a,2,3a,5,6a,9a,11,17,17a,20,23,26,29,32,35,38,41,44,47,50,53,56,59,67,70,73,76,79,82,85,88,91,97-tritriacontaoxo-12a,13a,19a,20a,63,64-hexathia-1a,3,4a,6,7a,10a,12,16a,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,68,71,74,77,80,83,86,89,92,98-tritriacontazahexacyclo[59.49.7.443,87.06,10.012,16.092,96]henicosahectan-2a-yl]propanoic acid

Synonyms

Crotamin

Purity

≥95%

Sequence

YKQC(1)HKKGGHC(2)FPKEKIC(3)LPPSSDFGKMDC(2)RWRWKC(1)C(3)KKGSG

Storage

Store at -20°C

InChI

InChI=1S/C214H326N64O54S7/c1-6-117(4)175-209(329)274-162-113-339-335-109-158(202(322)253-136(53-22-31-76-220)184(304)248-132(49-18-27-72-216)178(298)238-103-170(287)245-154(105-279)180(300)240-104-174(294)295)273-206(326)161-112-338-336-110-159(270-190(310)142(66-68-166(225)283)255-182(302)134(51-20-29-74-218)246-176(296)128(224)87-120-62-64-125(282)65-63-120)203(323)262-149(93-124-99-231-115-242-124)196(316)251-135(52-21-30-75-219)183(303)247-131(48-17-26-71-215)177(297)237-100-167(284)236-101-168(285)244-148(92-123-98-230-114-241-123)195(315)271-160(204(324)266-153(89-119-42-11-8-12-43-119)211(331)276-82-37-59-163(276)207(327)258-138(55-24-33-78-222)185(305)256-143(67-69-171(288)289)189(309)249-139(192(312)275-175)56-25-34-79-223)111-337-334-108-157(201(321)254-141(58-36-81-233-214(228)229)187(307)261-147(91-122-97-235-130-47-16-14-45-127(122)130)194(314)252-140(57-35-80-232-213(226)227)186(306)260-146(90-121-96-234-129-46-15-13-44-126(121)129)193(313)250-137(188(308)269-161)54-23-32-77-221)272-198(318)151(95-173(292)293)263-191(311)144(70-85-333-5)257-181(301)133(50-19-28-73-217)243-169(286)102-239-179(299)145(88-118-40-9-7-10-41-118)259-197(317)150(94-172(290)291)264-199(319)155(106-280)267-200(320)156(107-281)268-208(328)164-60-38-83-277(164)212(332)165-61-39-84-278(165)210(330)152(86-116(2)3)265-205(162)325/h7-16,40-47,62-65,96-99,114-117,128,131-165,175,234-235,279-282H,6,17-39,48-61,66-95,100-113,215-224H2,1-5H3,(H2,225,283)(H,230,241)(H,231,242)(H,236,284)(H,237,297)(H,238,298)(H,239,299)(H,240,300)(H,243,286)(H,244,285)(H,245,287)(H,246,296)(H,247,303)(H,248,304)(H,249,309)(H,250,313)(H,251,316)(H,252,314)(H,253,322)(H,254,321)(H,255,302)(H,256,305)(H,257,301)(H,258,327)(H,259,317)(H,260,306)(H,261,307)(H,262,323)(H,263,311)(H,264,319)(H,265,325)(H,266,324)(H,267,320)(H,268,328)(H,269,308)(H,270,310)(H,271,315)(H,272,318)(H,273,326)(H,274,329)(H,275,312)(H,288,289)(H,290,291)(H,292,293)(H,294,295)(H4,226,227,232)(H4,228,229,233)/t117-,128-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,175-/m0/s1

InChI Key

PEFQQQGFYPMQLH-WFQFKEFWSA-N

Canonical SMILES

CCC(C)C1C(=O)NC2CSSCC(NC(=O)C3CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3)CCCCN)CC4=CNC5=CC=CC=C54)CCCNC(=N)N)CC6=CNC7=CC=CC=C76)CCCNC(=N)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C8CCCN8C(=O)C9CCCN9C(=O)C(NC2=O)CC(C)C)CO)CO)CC(=O)O)CC2=CC=CC=C2)CCCCN)CCSC)CC(=O)O)C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CCC(=O)O)CCCCN)CC1=CC=CC=C1)CC1=CN=CN1)CCCCN)CCCCN)CC1=CN=CN1)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CC1=CC=C(C=C1)O)N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CO)C(=O)NCC(=O)O

1. Crotamine Cell-Penetrating Nanocarriers: Cancer-Targeting and Potential Biotechnological and/or Medical Applications

Mirian A F Hayashi, et al. Methods Mol Biol. 2020;2118:61-89. doi: 10.1007/978-1-0716-0319-2_5.

Crotamine is a basic, 42-residue polypeptide from snake venom that has been shown to possess cell-penetrating properties. Here we describe the preparation, purification, biochemical and biophysical analysis of venom-derived, recombinant, chemically synthesized, and fluorescent-labeled crotamine. We also describe the formation and characterization of crotamine-DNA and crotamine-RNA nanoparticles; and the delivery of these nanoparticles into cells and animals. Crotamine forms nanoparticles with a variety of DNA and RNA molecules, and crotamine-plasmid DNA nanoparticles are selectively delivered into actively proliferating cells in culture or in living organisms such as mice, Plasmodium, and worms. As such, these nanoparticles could form the basis for a nucleic acid drug-delivery system. We also describe here the design and characterization of crotamine-functionalized gold nanoparticles, and the delivery of these nanoparticles into cells. We also evaluated the viability of using the combination of crotamine with silica nanoparticles in animal models, aiming to provide slow delivery, and to decrease the crotamine doses needed for the biological effects. In addition, the efficacy of administering crotamine orally was also demonstrated.

2. Synthetic polypeptide crotamine: characterization as a myotoxin and as a target of combinatorial peptides

Celine Pompeia, et al. J Mol Med (Berl). 2022 Jan;100(1):65-76. doi: 10.1007/s00109-021-02140-9. Epub 2021 Oct 13.

Crotamine is a rattlesnake-derived toxin that causes fast-twitch muscle paralysis. As a cell-penetrating polypeptide, crotamine has been investigated as an experimental anti-cancer and immunotherapeutic agent. We hypothesized that molecules targeting crotamine could be designed to study its function and intervene in its adverse activities. Here, we characterize synthetic crotamine and show that, like the venom-purified toxin, it induces hindlimb muscle paralysis by affecting muscle contraction and inhibits KCNA3 (Kv1.3) channels. Synthetic crotamine, labeled with a fluorophore, displayed cell penetration, subcellular myofiber distribution, ability to induce myonecrosis, and bind to DNA and heparin. Here, we used this functionally validated synthetic polypeptide to screen a combinatorial phage display library for crotamine-binding cyclic peptides. Selection for tryptophan-rich peptides was observed, binding of which to crotamine was confirmed by ELISA and gel shift assays. One of the peptides (CVWSFWGMYC), synthesized chemically, was shown to bind both synthetic and natural crotamine and to block crotamine-DNA binding. In summary, our study establishes a functional synthetic substitute to the venom-derived toxin and identifies peptides that could further be developed as probes to target crotamine. KEY MESSAGES: Synthetic crotamine was characterized as a functional substitute for venom-derived crotamine based on myotoxic effects. A combinatorial peptide library was screened for crotamine-binding peptides. Tryptophan-rich peptides were shown to bind to crotamine and interfere with its DNA binding. Crotamine myofiber distribution and affinity for tryptophan-rich peptides provide insights on its mechanism of action.

3. Crotamine, a small basic polypeptide myotoxin from rattlesnake venom with cell-penetrating properties

Gandhi Rádis-Baptista, Irina Kerkis Curr Pharm Des. 2011 Dec;17(38):4351-61. doi: 10.2174/138161211798999429.

Crotamine, a low molecular weight cationic polypeptide from the venom of the South American rattlesnake Crotalus durissus terrificus is a natural cell-penetrating peptide with functional versatility. The presence of nine lysine residues and three disulfide bonds renders crotamine highly compact, stable and positively charged. Topologically, crotamine adopts an ancient β-defensin fold that is found in diverse families of endogenous and venom polypeptides dedicated to host defense. Crotamine is unique among several classes of bioactive peptides because it possesses both cell penetrating and antimicrobial activities and selective biological action toward some cell types at a given cell cycle phase. Because it can rapidly and efficiently translocate into actively proliferating cells, crotamine is being investigated for labeling highly replicating cells and for use as a chemotherapeutic adjuvant. Peptides derived from crotamine, nucleolar targeting peptides (NrTPs), have been designed and are being studied. NrTPs retain some crotamine properties, such as efficient cellular uptake and preferential nuclear localization whereas they improve upon other properties. For example, NrTPs are smaller than crotamine, show higher preferential nucleolar localization, and better facilitate ZIP-code localization of therapeutic proteins.