1417221-06-7
Chemical Structure
Cys(Npys)-(Arg)9
- CAS No.: 1417221-06-7
- Formula:C62H118N40O12S2
- Molecular Weight:1679.99
IUPAC Name: (2R,5S,8S,11S,17S,20S)-20-((S)-2-((R)-2-amino-3-mercaptopropanamido)-5-guanidinopentanamido)-8-(4-aminobutyl)-11-(3-guanidinopropyl)-2-(mercaptomethyl)-5,17-dimethyl-4,7,10,13,16,19-hexaoxo-3,6,9,12,15,18-hexaazatricosanedioic acid
InChIKey: IJZUWTDQAPPMMA-CJSHHNLHSA-N
SMILES: N=C(N)NCCC[C@@H](C(N)=O)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@@H](N)CSSC1=C(C=CC=N1)[N+]([O-])=O)=O)=O)=O)=O)=O)=O)=O)=O)=O
Biological Activity: Cys(Npys)-(Arg)9 is a synthetic cationic cell-penetrating peptide with a reversible thiol-reactive nitropyridyl (Npys) group. Cys(Npys)-(Arg)9 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 endows TALEN proteins with cell-penetrating activity, enabling gene knockout in mammalian cells and protein transduction in wheat microspores. Cys(Npys)-(Arg)9 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 to loaded molecules is higher than 1:1, it exerts certain cytotoxic effects on cells. Cys(Npys)-(Arg)9 can be used in studies related to oral squamous cell carcinoma and HIV infection[1][2][3][4][5].
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Cys(Npys)-(Arg)9 | Cys(Npys)-(Arg)9 is a synthetic cationic cell-penetrating peptide with a reversible thiol-reactive nitropyridyl (Npys) group. Cys(Npys)-(Arg)9 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 endows TALEN proteins with cell-penetrating activity, enabling gene knockout in mammalian cells and protein transduction in wheat microspores. Cys(Npys)-(Arg)9 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 to loaded molecules is higher than 1:1, it exerts certain cytotoxic effects on cells. Cys(Npys)-(Arg)9 can be used in studies related to oral squamous cell carcinoma and HIV infection. | |||||||||||||||||||||
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References
- [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. [Content Brief]
- [2]. Yamayoshi A, et al. Development of Antibody-Oligonucleotide Complexes for Targeting Exosomal MicroRNA. Pharmaceutics. 2020;12(6):545. Published 2020 Jun 12. [Content Brief]
- [3]. Kim SS, et al. Antibody-mediated delivery of siRNAs for anti-HIV therapy. Methods Mol Biol. 2011;721:339-353. [Content Brief]
- [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]
