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Seung Il Kim,Chang Mo Son,Young Sil Jeon,Ji-Heung Kim 대한화학회 2009 Bulletin of the Korean Chemical Society Vol.30 No.12
Novel poly(aspartic acid) derivatives conjugated with γ-amino butyric acid, GABA, moieties, and their amphiphilic analogs were synthesized and characterized. The chemical structures of these polymers were confirmed by FT-IR and 1H NMR spectroscopy. Their physicochemical properties in aqueous media were characterized by electrophonetic light scattering spectrophotometry (ELS), acid-base titration, and UV-spectroscopy. In addition, the in vitro cell activity of the GABA-conjugated polymer was examined. These results indicated that GABA-conjugated poly(aspartic acid) derivatives showed cell-growth activity and nanoparticle formation of a suitable size within aqueous media. These polymers have potential application in the cosmetic and pharmaceutical fields.
Kim, Seung-Il,Son, Chang-Mo,Jeon, Young-Sil,Kim, Ji-Heung Korean Chemical Society 2009 Bulletin of the Korean Chemical Society Vol.30 No.12
Novel poly(aspartic acid) derivatives conjugated with $\gamma$-amino butyric acid, GABA, moieties, and their amphiphilic analogs were synthesized and characterized. The chemical structures of these polymers were confirmed by FT-IR and $^1H$ NMR spectroscopy. Their physicochemical properties in aqueous media were characterized by electrophonetic light scattering spectrophotometry (ELS), acid-base titration, and UV-spectroscopy. In addition, the in vitro cell activity of the GABA-conjugated polymer was examined. These results indicated that GABA-conjugated poly(aspartic acid) derivatives showed cell-growth activity and nanoparticle formation of a suitable size within aqueous media. These polymers have potential application in the cosmetic and pharmaceutical fields.
아미노산 곁사슬 치환 폴리아스팔트산계 생분해성 고흡수성 젤의 제조와 물성
김지흥(Ji Heung Kim),손창모(Chang Mo Son),전영실(Young Sil Jeon) 한국고분자학회 2011 폴리머 Vol.35 No.6
생체적합하고 생분해성을 갖는 폴리아미노산의 하나인 폴리아스팔트산은 팹타이드 결합으로 이루어진 수용성 합성고분자로서 의료용 소재 및 다양한 응용분야의 연구가 흥미있게 진행되어 왔다. 본 연구에서는 아미노산인 GABA(γ-aminobutylic acid)와 β-alanine을 곁사슬에 도입한 폴리아스팔트산 유도체 고분자를 제조하고, 이들을 서로 다른 함량의 ethylene glycol diglycidyl ether(EGDE)를 사용하여 가교시켜 고흡수성 하이드로젤을 제조하였 다. 각 하이드로젤에 대해 증류수와 PBS 용액에서 기본적인 팽윤물성, 젤의 가수분해 거동과 모폴로지를 조사하였 다. 제조한 하이드로젤은 수용액에서 pH와 염(salt) 농도에 의존하는 민감성 팽윤거동을 보였으며, 또한 비교적 빠 른 가수분해 거동을 나타내었다. The biocompatibility and biodegradability of poly(amino acid) make them ideal candidates for many bio-related applications. Poly(aspartic acid), PASP, is one of synthetic water-soluble polymers with proteinlike structure, and has been extensively explored for the potential industrial and biomedical applications due to its biodegradable, biocompatible and pH-responsive properties. In this work, amino acid-conjugated PASPs were prepared by aminolysis reaction onto polysuccinimide (PSI) using γ-aminobutylic acid(GABA) and β- alanine methyl ester and a subsequent hydrolysis process. Their chemical gels were prepared by crosslinking reaction with ethylene glycol diglycidyl ether (EGDE). The hydrogels were investigated for their basic swelling behavior, hydrolytic degradation and morphology. The crosslinked gels showed a responsive swelling behavior, which was dependent on pH and salt concentration in aqueous solution, and relatively fast hydrolytic degradation.
김지훈,오영택,이경수,윤정민,박병태,오경택 한국고분자학회 2011 Macromolecular Research Vol.19 No.5
pH sensitive polymer systems can be utilized as smart nanocarriers to deliver hydrophobic drugs specifically to solid tumors or to acidosis-affected rheumatic joints. In this study, a poly(L-aspartic acid-graftimidazole)-block-poly(ethylene glycol) (P(Asp-g-Im)-PEG) block copolymer was synthesized as a pH sensitive nanocarrier targeting acidic pH environments. The polypeptide P(Asp), which was used as a backbone for the hydrophobic block, was synthesized by ring opening polymerization with N-carboxylanhydride (NCA) of β-benzyl-aspartic acid. PEG was included as the hydrophilic block and the polymer was functionalized with imidazole groups to confer pH sensitivity. The prepared P(Asp-g-Im)-PEG is zwitterionic with a pI 6.5; 60%of the available carboxyl groups of P(Asp)-PEG were substituted by imidazole groups. Furthermore, the potentiometric titration curve of P(Asp-g-Im)-PEG demonstrated a broad buffer zone. The micelles prepared from P(Asp-g-Im)-PEG showed pH dependent critical micelle concentrations (CMC), particle sizes, zeta potentials,and morphologies.
Synthesis and Characterization of Novel Amino Acid-conjugated Poly(aspartic acid) Derivatives
Ji-Heung Kim,Seung Il Kim,Seok Kee Min 대한화학회 2008 Bulletin of the Korean Chemical Society Vol.29 No.10
Novel poly(aspartic acid) derivatives conjugated with L-lysine moieties and their amphiphilic analogs were synthesized and characterized. The chemical structures of these polymers were confirmed using FT-IR and 1HNMR spectroscopy. The physicochemical properties of amphiphilic copolymers were characterized using an electrophonetic light scattering spectrophotometer (ELS) and transmission electron microscopy (TEM). These results indicated a stable nanoparticle formation within aqueous media. These polymers have potential applications in the pharmaceutical and cosmetic fields as delivery vehicles for bioactive molecules.
Synthesis and Characterization of Novel Amino Acid-conjugated Poly(aspartic acid) Derivatives
Kim, Seung-Il,Min, Seok-Kee,Kim, Ji-Heung Korean Chemical Society 2008 Bulletin of the Korean Chemical Society Vol.29 No.10
Novel poly(aspartic acid) derivatives conjugated with L-lysine moieties and their amphiphilic analogs were synthesized and characterized. The chemical structures of these polymers were confirmed using FT-IR and $^1HNMR$ spectroscopy. The physicochemical properties of amphiphilic copolymers were characterized using an electrophonetic light scattering spectrophotometer (ELS) and transmission electron microscopy (TEM). These results indicated a stable nanoparticle formation within aqueous media. These polymers have potential applications in the pharmaceutical and cosmetic fields as delivery vehicles for bioactive molecules.
Yoo, Bong Kyu,Jalil Miah, Md Abdul,Lee, Eung-Seok,Han, Kun Pharmaceutical Society of Japan 2006 Biological & pharmaceutical bulletin Vol.29 No.8
<P>A partially benzylated poly-<SMALL>L</SMALL>-aspartic acid (PBPA) was synthesized and investigated as a potential renal protective agent for the toxicity of amphotericin B (AmB) when the drug was administered as nanoparticular micelle. Nanoparticular AmB micelles were prepared by slow dialysis of the drug against distilled water at the elevated pH of 11.5 and subsequent sonication with the polymer solution. The resulting nanoparticular AmB micelles with PBPA showed an average diameter of about 20 nm and demonstrated significantly less damage to the tubular cells of the rat's kidney in terms of transmission electron microscopic study. There was little or no damage on the brush border of tubular cells 7 d after single intravenous dose of AmB 5 mg/kg in the rats when the drug was administered as nanoparticuar micelles with PBPA. The reduced renal toxicity appears to be due to the alteration of self-aggregation status of AmB. Molar absorptivity of AmB at 412 nm (a marker for the prevalence of non-aggregated AmB) was significantly higher in the nanoparticular AmB micelles with PBPA than those in AmB micelles without PBPA as well as in Fungizone<SUP>®</SUP>. This result indicates an association of the reduced nephrotoxicity and the prevalence of non-aggregated AmB. Mechanisms for the reduced renal toxicity may also include the formation of electrostatic complex between anionic groups of PBPA and hydroxyl groups of AmB.</P>
Jun Yang,Fang Wang,Tianwei Tan 한국화학공학회 2008 Korean Journal of Chemical Engineering Vol.25 No.5
A novel soil stabilizer based on poly-amino acid - polyaspartic acid (PASP) and its copolymer which modified by xanthan gum (XG) was studied to increase soil particle compressive strength and resistance to wind erosion. Due to its unique property, the stabilizer aggregated individual soil particles and formed crust. The sample compressive strength increased from 0.175 to 0.612MPa and the wind erosion modulus reduced from 22.43 to 10.56 g·m−2·min−1 after the 1% PASP hydrogel was applied by 1.67 Lm−2 (1 cm of crust). The soil water content was higher than the control due to the polymer’s excellent water-retaining property. The polymer had no negative influence on seed germination and growth. The biodegradability experiment showed that PASP was easy to biodegrade and therefore it was safe to apply in the field.
Poly(aspartic acid)를 이용한 조직공학용 지지체의 제조 및 특성(1)
배홍기,김지흥,안정호,정동준 한국생체재료학회 2008 생체재료학회지 Vol.12 No.4
One of the most important properties of synthetic materials for biomedical applications is that the materials should have biostability, biocompatibility and biodegradability. Polypeptides which are made of amino acids is useful to biomedical application because they are main structural materials of biosystem. Poly(aspartic acid) (PAsp) is synthesized by polymerization of the corresponding N-carboxyamino acid anhydride (NCA) in solution in the presence of suitable catalysts. However, the NCA method has processing problems in synthesis and cost disadvantage comparing to other methods. Recently, a simple polycondensation method of L-aspartic acid in the presence of acid catalyst was developed and we can get the high molecular weight of PAsp by this method. In this study, PAsp hydrogels have been prepared by the cross-linking reaction of PAsp produced by thermal polycondensation reactions with an acid catalyst. The molecular weight of synthesized PAsp was about 50,000 (Mw, whereas DP = 500). And the PAsp hydrogels were formed above 10 mol% of cross-linker(ethylene diamine) concentration. The water absorption capacity of the PAsp hydrogel in deionized water was measured and the maximum capacity was 1,400%. We found that the synthesized PAsp hydrogels obtained the interconnected porous structure (pore size was about 100~200 μm) by scanning electron microscopy observation. The cytotoxicity test was carried out on the PAsp hydrogel using the fibroblast cells. After four days incubation, the fibroblast cells adhered and spread well on the PAsp hydrogel. Futhermore, the fibroblast cells proliferated well on the PAsp hydrogel compared with the control cells on the cell culture plate. These results strongly indicated that the PAsp hydrogels can be used as the scaffold for tissue engineering applications.