Cys(Npys)-(Arg)9 acetate 

Cys(Npys)-(Arg)9 acetate is a synthetic cationic cell-penetrating peptide with a reversible thiol-reactive nitropyridyl (Npys) group. Cys(Npys)-(Arg)9 acetate efficiently mediates the internalization and delivery of various "cargo" such as proteins and antibodies by forming reversible disulfide bonds with surface-exposed cysteine residues. Cys(Npys)-(Arg)9 acetate endows TALEN proteins with cell-penetrating activity, enabling gene knockout in mammalian cells and protein transduction in wheat microspores. Cys(Npys)-(Arg)9 acetate can be conjugated with antibodies to form cationized IgG for enhancing endosomal escape of oligonucleotides, or form siRNA delivery complexes. When the molar ratio of Cys(Npys)-(Arg)9 acetate to loaded molecules is higher than 1:1, it exerts certain cytotoxic effects on cells. Cys(Npys)-(Arg)9 acetate can be used in studies related to oral squamous cell carcinoma and HIV infection^{[1][2][3][4][5]}.

Upon conjugation with CCR5-targeting TALEN protein, Cys(Npys)-(Arg)9 acetate induces CCR5 gene knockout in HeLa cells at a frequency of approximately 16% when delivered at a peptide-to-protein ratio of 8:1 or 15:1 (1 μM; 2 hr)^[1].
After conjugation of Cys(Npys)-(Arg)9 acetate to TALEN proteins targeting BMPR1A, delivery at peptide-to-protein ratios of 1:1, 2:1 or 4:1 (1 μM; 2 h) induces knockout of the BMPR1A gene in HEK 293 cells, with a maximum frequency of up to 4%^[1].
Cys(Npys)-(Arg)9 acetate-conjugated TALEN proteins do not reduce the viability of HeLa cells or HEK 293 cells^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

1679.99 (free base)

C₆₂H₁₁₈N₄₀O₁₂S₂·xC₂H₄O₂

Solid

Off-white to light yellow

Cys(Nyps)-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-NH2

C(Npys)RRRRRRRRR-NH2

Room temperature in continental US; may vary elsewhere.

Sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

• [1]. Liu J, et al. Cell-penetrating peptide-mediated delivery of TALEN proteins via bioconjugation for genome engineering. PLoS One. 2014;9(1):e85755. Published 2014 Jan 20.

  [2]. Yamayoshi A, et al. Development of Antibody-Oligonucleotide Complexes for Targeting Exosomal MicroRNA. Pharmaceutics. 2020;12(6):545. Published 2020 Jun 12.

  [3]. Kim SS, et al. Antibody-mediated delivery of siRNAs for anti-HIV therapy. Methods Mol Biol. 2011;721:339-353.

  [4]. Sinha R K, et al. TALE protein mediated overexpression of embryogenesis related marker genes in wheat microspores[J]. South African Journal of Botany, 2021, 138: 50-56.

  [5]. Bilichak A, et al. Intracellular delivery of fluorescent protein into viable wheat microspores using cationic peptides. Front Plant Sci. 2015;6:666. Published 2015 Aug 28.  [Content Brief]