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Cys-HIV-Tat (47-57,Rr)

Trifluoroacetate

Cat. No. Amount Price (EUR) Buy / Note
CPP-P12 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: 1562 Da confirmed by MALDI-MS, peptide provides 7 positive charges in side chains for complex formation with DNA and pDNA. Up to 7 trifluoroacetate residues may be present resulting in an apparent MW of 3.0 kDa.

Purity: ≥ 95 % (HPLC)

Form: powder

Solubility: water

Description:
HIV-Tat (47-57) is an arginine rich cell penetrating peptide derived from the HIV-1 transactivating protein. The internalization of HIV-Tat (47-57)-cargo complex mainly occurs through endocytosis or macro-pinocytosis and the efficiency of cytosolic delivery is often hampered by endosomal entrapment of the complex.
HIV-Tat (47-57) with alternating chirality of arginine (HIV-Tat (47-57, rR) however, achieves improved cytosolic delivery[1] and triggers endosomal escape[2]. The uptake occurs rather by direct membrane translocation than through endocytosis.
Cys-functionalized HIV-Tat (47-57, Rr) 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 reaction[3]). Improved coupling with maleimide derivatives are described[4,5].
  • bromomethyl-phenyl-functionalized label[6,7]

Stock solution:
For non-covalent complex formation, dissolve 50 μg in 150 μl 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] Yan Ma et al. (2012) Direct cytosolic delivery of cargoes in vivo by a chimera consisting of D- and L-arginine residues. J. Control. Release 162:286.
[2] Erazo-Oliveras et al. (2012) Improving endosomal escape of cell-penetrating peptides and their cargos: strategies and challenges. Pharmaceuticals 5:1177.
[3] 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.
[4] 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.
[5] Badescu et al. (2014) A new reagent for stable thiol-specific conjuagtion. Bioconjugate Chem. 25:460.
[6] Smeenk et al. (2012) Synthesis of water-soluble scaffolds for peptide cyclization, labeling and ligation. Organic Lett. 14 (5):1194.
[7] Dewkar et al. (2012) Synthesis of novel peptide linkers: simultaneous cyclization and labeling. Organic Lett. 11 (20):4708.