| 학회 | 한국공업화학회 |
| 학술대회 | 2015년 봄 (04/29 ~ 05/01, BEXCO (부산)) |
| 권호 | 19권 1호 |
| 발표분야 | 정밀화학_포스터 |
| 제목 | A Study of Oligopeptide Derivatives: Synthesis and Biological Activity |
| 초록 | In this study, some known, basic oligopeptide derivatives were synthesized and then conjugated with cinnamic acid (CN) 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). Cinnamic acid (CN) 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 52-67 % after 4-6 h for cinnamic-tripeptide (CN-GHK), cinnamic-pentapeptides (CN-KTTKS) and cinnamic-hexapeptide (CN-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, CN-EEMQRR was only dissolved in CHCl3. The biological activity of the conjugated oligopeptides was investigated. Hexapeptide derivatives CN-EEMQRR showed the cytotoxic while the other derivatives did not show this effect even at high concentration of 200 µg/ml. CN-GHK and CN-KTTKS showed 14.3-15.5% anti-inflammatory effect via nitric oxide inhibition at 100 µg/ml concentration. From the the MMP-1 inhibition experiments, CN-GHK and CN-KTTKS showed the anti-wrinkle effect with the inhibition rate of more than 20% at 0.063 mM concentration. In summary, it can be inferred from our experimental results that CN-GHK and CN-KTTKS may be recognized as the new potential drugs and functional cosmetic materials for industrial applications. |
| 저자 | 김보미, 김미진, 김후희, 양두리, 임효, 채규윤 |
| 소속 | 원광대 |
| 키워드 | oligo pepetide; solid phase peptide synthesis (SPPS); cinnamic acid; biological activity |
