GRGDSPC TFA

• CAT Number: I045791
• Molecular Formula: C27H43F3N10O13S
• Molecular Weight: 804.75
• Purity: ≥95%
• Synonyms: (3S)-3-[[2-[[(2S)-2-[(2-aminoacetyl)amino]-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-4-[[(2S)-1-[(2S)-2-[[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl]amino]-4-oxobutanoic acid;2,2,2-trifluoroacetic acid
• InChI: InChI=1S/C25H42N10O11S.C2HF3O2/c26-8-17(37)31-12(3-1-5-29-25(27)28)20(41)30-9-18(38)32-13(7-19(39)40)21(42)33-14(10-36)23(44)35-6-2-4-16(35)22(43)34-15(11-47)24(45)46;3-2(4,5)1(6)7/h12-16,36,47H,1-11,26H2,(H,30,41)(H,31,37)(H,32,38)(H,33,42)(H,34,43)(H,39,40)(H,45,46)(H4,27,28,29);(H,6,7)/t12-,13-,14-,15-,16-;/m0./s1
• InChIKey: JLXWPECCGJGSMS-MHXJNQAMSA-N
• SMILES: C1CC(N(C1)C(=O)C(CO)NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CCCN=C(N)N)NC(=O)CN)C(=O)NC(CS)C(=O)O.C(=O)(C(F)(F)F)O

GRGDSPC TFA, a 7-amino acid peptide, is a thiolated cell adhesion peptide[1].
GRGDSPC is conjugated to acrylated dextran via thiol-acrylate reaction to regulate the interactions of human mesenchymal stem cells (hMSCs) with the photocrosslinkable hydrogels. To determine the conjugation kinetics and efficiency of GRGDSPC peptide to DEX-MAES16, various GRGDSPC concentrations (i.e., 5, 10 and 20 mg/1 g DEX-MAES16) are conjugated to the acrylated Dextran (DEX) macromer over time (0.25, 0.5, 1 and 3h) in PBS at pH 7.8 and the free thiol groups of unreacted peptides are quantified using Ellman’s assay. In addition, the reaction kinetics of the thiol-peptide to acrylated (DEX-MAES16) and methacrylated (DEX-HEMA16) macromers are compared. As early as 15 min conjugation, with 5, 10 and 20 mg of GRGDSPC peptide/1 g modified DEX, the peptide conjugation efficiencies with DEX-MAES are 105.40, 94.10 and 87.45%, respectively, while for the reaction with the DEX-HEMA they are 0.73, 15.78 and 18.42%, respectively. After 1h, the GRGDSPC conjugation with DEX-MAES is completed with the peptide concentration of 10 mg, but only 35.66% of the thiol groups of the peptide react with DEX-HEMA. The reaction kinetics are also monitored at 3 h of conjugation, and all of the 20 mg GRGDSPC peptide reacts with acrylated DEX compared to only 32.53% for the methacrylated DEX at this time point[1].

Reference

[1]. Nguyen MK, et al. Photocrosslinkable, biodegradable hydrogels with controlled cell adhesivity for prolonged siRNAdelivery to hMSCs to enhance their osteogenic differentiation. J Mater Chem B. 2017 Jan 21;5(3):485-495.
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