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H-Tyr-Ile-Gly-Ser-Arg-NH2

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

H-Tyr-Ile-Gly-Ser-Arg-NH2 binds to laminin receptor and inhibits experimental metastasis formation. Compared with YIGSR, C-terminal amidation significantly increases peptide activity.

Category

Peptide Inhibitors

Catalog number

BAT-015171

CAS number

110590-65-3

Molecular Formula

C26H43N9O7

Molecular Weight

593.68

Specification
Reference Reading

IUPAC Name

(2S,3S)-N-[2-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanamide

Synonyms

YIGSR amide; H-YIGSR-NH2; L-Argininamide, L-tyrosyl-L-isoleucylglycyl-L-seryl-; L-tyrosyl-L-isoleucyl-glycyl-L-seryl-L-argininamide; L-Tyrosyl-L-isoleucylglycyl-L-seryl-N5-(diaminomethylene)-L-ornithinamide

Appearance

White or Off-white Lyophilized Powder

Purity

95%

Density

1.44±0.1 g/cm3 (Predicted)

Sequence

Tyr-Ile-Gly-Ser-Arg-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C26H43N9O7/c1-3-14(2)21(35-23(40)17(27)11-15-6-8-16(37)9-7-15)25(42)32-12-20(38)33-19(13-36)24(41)34-18(22(28)39)5-4-10-31-26(29)30/h6-9,14,17-19,21,36-37H,3-5,10-13,27H2,1-2H3,(H2,28,39)(H,32,42)(H,33,38)(H,34,41)(H,35,40)(H4,29,30,31)/t14-,17-,18-,19-,21-/m0/s1

InChI Key

HVZPPZGCZLLMBC-LJZWMIMPSA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(CO)C(=O)NC(CCCN=C(N)N)C(=O)N)NC(=O)C(CC1=CC=C(C=C1)O)N

1. Peptide functionalized polyhydroxyalkanoate nanofibrous scaffolds enhance Schwann cells activity

Elahe Masaeli, Mohammad Morshed, Lorenzo Moroni, Clemens A van Blitterswijk, Mohammad H Nasr-Esfahani, Paul A Wieringa, Saeid Sadri Nanomedicine . 2014 Oct;10(7):1559-69. doi: 10.1016/j.nano.2014.04.008.

Interactions between Schwann cells (SCs) and scaffolds are important for tissue development during nerve regeneration, because SCs physiologically assist in directing the growth of regenerating axons. In this study, we prepared electrospun scaffolds combining poly (3-hydroxybutyrate) (PHB) and poly (3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) functionalized with either collagen I, H-Gly-Arg-Gly-Asp-Ser-OH (GRGDS), H-Tyr-Ile-Gly-Ser-Arg-NH2 (YIGSR), or H-Arg-Asn-Ile-Ala-Glu-Ile-Ile-Lys-Asp-Ile-OH (p20) neuromimetic peptides to mimic naturally occurring ECM motifs for nerve regeneration. Cells cultured on fibrous mats presenting these biomolecules showed a significant increase in metabolic activity and proliferation while exhibiting unidirectional orientation along the orientation of the fibers. Real-time PCR showed cells cultured on peptide-modified scaffolds had a significantly higher neurotrophin expression compared to those on untreated nanofibers. Our study suggests that biofunctionalized aligned PHB/PHBV nanofibrous scaffolds may elicit essential cues for SCs activity and could serve as a potential scaffold for nerve regeneration. From the clinical editor: Nanotechnology-based functionalized scaffolds represent one of the most promising approaches in peripheral nerve recovery, as well as spinal cord recovery. In this study, bio-functionalized and aligned PHB/PHBV nanofibrous scaffolds were found to elicit essential cues for Schwann cell activity, therefore could serve as a potential scaffold for nerve regeneration.