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Cys-Crotamine

Trifluoroacetate

Cat. No. Amount Price (EUR) Buy / Note
CPP-P13 50 μg 150,00 Add to Basket/Quote Add to Notepad

For in vitro use only!

Shipping: shipped on blue ice

Storage Conditions: store at -20 °C
protect from light

Shelf Life: 12 months

Molecular Weight: 1591.8 Da confirmed by MALDI-MS, peptide provides 7 positive charges in side chains for complex formation. 7 trifluoroacetate residues may be present resulting in an apparent MW of 2.5 kDa.

Purity: ≥ 95 % (HPLC)

Form: powder

Solubility: water

Description:
Crotamine is a fragment of a toxin from South American rattlesnake Crotallus durissus terrificus venom. It accumulates in cell nucleoli and is therefore also termed nucleolar targeting peptide (NrTP). Internalization involves binding to heparan sulfate proteoglycans, followed by endocytosis and leakage of vesicle content to the cytosole[1]. Crotamine delivers in vitro and in vivo mainly into actively proliferating cells[2] leading to an expressed selectivity for tumor cells.
As a positively charged peptide it can stimulate the uptake of DNA and plasmids through electrostatically complex formation[3].
Cys-functionalized Crotamine allows covalent coupling of thiol reactive compounds e.g.

  • maleimide-functionalized label (without addition of glutathione and Tris-(2-carboxy ethyl)phosphine within the labeling reaction4). Improved coupling with maleimide derivatives are described[5,6].
  • bromomethyl-phenyl-functionalized label[7,8]

Stock solution:
For non-covalent complex formation, dissolve 50 μg in 0.2 ml sterile and oxygen-free water according to the general manual. Use the solution immediately or aliquot and store at -20 °C. Avoid freeze / thaw cycles.
Usage:
Perform calculation, complex formation and cargo transduction according to detailed protocols given in the general manual. For covalent coupling of cargo use instructions from Jena Bioscience Kit or take detailed instructions from attached references.

Selected References:
[1] Nascimento et al. (2007) Crotamine mediates gene delivery into cells through the binding to heparin sulfate proteoglycans. J. Biol. Chem. 282 (29):21349.
[2] Rodrigues et al. (2011) Efficient cellular delivery of β-galactosidase mediated by NrTPs, a new family of cell-penetrating peptides. Bioconjugate Chemistry 22:2339.
[3] Radis-Baptista et al. (2011) Crotamine, a small basic polypeptide myotoxin from rattlesnake venom with cell-penetrating properties. Current pharmacol. Design 17:4351.
[4] Tansi et al. (2015) Internalization of near-infrared fluorescently labeled activatable cell-penetrating peptide and of proteins into human fibrosarcoma cell line HT-1080. J. Cell. Biochem. 116:1222.
[5] Ryan et al. (2011) Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis. Chem. Commun. 47:5452.
[6] Badescu et al. (2014) A new reagent for stable thiol-specific conjuagtion. Bioconjugate Chem. 25:460.
[7] Smeenk et al. (2012) Synthesis of water-soluble scaffolds for peptide cyclization, labeling and ligation. Organic Lett. 14 (5):1194.
[8] Dewkar et al. (2012) Synthesis of novel peptide linkers: simultaneous cyclization and labeling. Organic Lett. 11 (20):4708.