| 학회 | 한국공업화학회 |
| 학술대회 | 2015년 봄 (04/29 ~ 05/01, BEXCO (부산)) |
| 권호 | 19권 1호 |
| 발표분야 | 정밀화학_포스터 |
| 제목 | A Study of PEGylated-Oligopeptide Derivatives: Synthesis and Biological Activity |
| 초록 | In this study, some known, basic oligopeptide derivatives were synthesized and then conjugated with gallic acid (GA) through the peptide bindings between the amine (-NH2) and carboxylic acid (-COOH) moieties to improve their anti-wrinkle effect. The solubility and bioactivity of these novel conjugated oligopeptides were investigated for the development of new drugs and functional cosmetic materials. For the synthesis of the designed conjugated oligopeptides, first, the known, basic tripeptide (Gly–His-Lys : GHK), pentapeptide (Lys–Thr–Thr–Lys–Ser : KTTKS), and hexapeptide (Glu–Glu–Met–Gln–Arg-Arg : EEMQRR) were linked to the resin by the solid phase peptide synthesis (SPPS). The linking yields were depended on the chains of the amino acid sequences in the peptides. The longer chain of the amino acid sequence gave the lower yield. Second, PEGylated 3,4,5-triacetoxy benzoic acid (GA-PEG) was incorporated with the basic solid peptides by using the DIC and HOBt coupling reagents at 30oC. The Kaiser test of the free amino acid groups was used to monitor the reaction. Finally, the trifluoroacetic acid (TFA) cleavages from the solid supports gave the desired oligopeptides in the moderate yields such as 38-45 % after 10-14 h for PEGylated 3,4,5-triacetoxy benzoic tripeptide (GA-PEG-GHK), PEGylated 3,4,5-triacetoxy benzoic pentapeptide (GA-PEG-KTTKS) and PEGylated 3,4,5-triacetoxy benzoic hexapeptide (GA-PEG-EEMQRR). The solubility of the conjugated oligopeptides was examined. In almost cases, the synthesized oligopeptides were soluble in water, methanol, and dichloromethane and were very soluble in DMSO. However, hexapeptide derivatives GA-PEG-EEMQRR was only dissolved in CHCl3. The biological activity of the conjugated oligopeptides was investigated. We tried anti-oxidation activity, anti-inflammatory effect via nitric oxide inhibition, anti-wrinkle effect experiment and get good results. It can be inferred from our experimental results that GA-PEG-GHK and GA-PEG-KTTKS may be recognized as the new potential drugs and functional cosmetic materials for industrial applications. |
| 저자 | 김미진, 김보미, 양두리, 정성훈, 채규윤 |
| 소속 | 원광대 |
| 키워드 | PEGylation; oligo pepetide; solid phase peptide synthesis (SPPS); biological activity |
