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( Bieong Kil Kim ),( Kyung Oh Doh ),( Guen Bae Hwang ),( Young Bae Seu ) 한국미생물 · 생명공학회 2012 Journal of microbiology and biotechnology Vol.22 No.6
A novel cholesterol-based cationic lipid containing a tri-2- hydroxyethylamine head group and ether linker (Chol- THEA) was synthesized and examined as a potent gene delivery vehicle. In the preparation of cationic liposome, the addition of DOPE as helper lipid significantly increased the transfection efficiency. To find the optimum transfection efficiency, we screened various weight ratios of DOPE and liposome/DNA (N/P). The best transfection efficiency was found at the Chol-THEA:DOPE weight ratio of 1:1 and N/P weight ratio of 10~15. Most of the plasmid DNA was retarded by this liposome at the optimum N/P weight ratio of 10. The transfection efficiency of Chol-THEA liposome was compared with DOTAP, Lipofectamine, and DMRIE-C using the luciferase assay and GFP expression. Chol-THEA liposome with low toxicity had better or similar potency of gene delivery compared with commercial liposomes in COS-7, Huh-7, and MCF-7 cells. Therefore, Chol-THEA could be a useful non-viral vector for gene delivery.
Kim, Bieong-Kil,Seu, Young-Bae,Bae, Yun-Ui,Kwak, Tae-Won,Kang, Hyungu,Moon, Ik-Jae,Hwang, Guen-Bae,Park, So-Young,Doh, Kyung-Oh Molecular Diversity Preservation International (MD 2014 INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES Vol.15 No.5
<P>Cationic liposomes are broadly used as non-viral vectors to deliver genetic materials that can be used to treat various diseases including cancer. To circumvent problems associated with cationic liposome-mediated delivery systems such as low transfection efficiency and serum-induced inhibition, cholesterol-based cationic lipids have been synthesized that resist the effects of serum. The introduction of an ether-type linkage and extension of the aminopropyl head group on the cholesterol backbone increased the transfection efficiency and DNA binding affinity compared to a carbamoyl-type linkage and a mono aminopropyl head group, respectively. Under optimal conditions, each liposome formulation showed higher transfection efficiency in AGS and Huh-7 cells than commercially available cationic liposomes, particularly in the presence of serum. The following molecular structures were found to have a positive effect on transfection properties: (i) extended aminopropyl head groups for a strong binding affinity to plasmid DNA; (ii) an ether linkage that favors electrostatic binding to plasmid DNA; and (iii) a cholesterol backbone for serum resistance.</P>
Synthesis of NBD-Labeled DOTAP Analog to Track Intracellular Delivery of Liposome
( Kyung Oh Doh ),( Bieong Kil Kim ),( Tae Jin Lee ),( Jong Won Park ),( Young Bae Seu ) 한국미생물 · 생명공학회 2013 Journal of microbiology and biotechnology Vol.23 No.1
A DOTAP analog labeled by NBD on the head group (DTNBD) was designed and synthesized to label DOTAP liposome. The structure was confirmed by 1H NMR and FAB-MS, and the fluorescence of the newly synthesized DT-NBD was observed by fluorescent microscopy. The transfection efficiency of DOTAP liposome containing DT-NBD was comparable to commonly used NBD PE in COS7 and MCF7 cells. Furthermore, the level of cellular uptake and fluorescent intensity of fluorescent liposome containing DT-NBD was higher than NBD PE. Therefore, the novel NBD-labeled DOTAP analog seems to be effectively used for investigation of the cellular interaction and transfection mechanism of DOTAP liposome.
Synthesis of cholesteryl doxorubicin and its anti-cancer activity
Choi, Jong-Soo,Doh, Kyung-Oh,Kim, Bieong-Kil,Seu, Young-Bae Pergamon Press 2017 Bioorganic & medicinal chemistry letters Vol.27 No.4
<P><B>Abstract</B></P> <P>Doxorubicin (dox) has been used as anti-cancer agent, but there are disadvantages such as rapid excretion, short retention time and cardiotoxicity. For giving lipophilic properties to dox, it was modified with cholesterol derivatives that were validated as a component of liposomal gene delivery. This article describes the synthesis of dox derivatives (lipo-dox A-D), their cytotoxicity and cellular uptake. In A549, HeLa, MCF7 and MDA MB 231 cell lines, lipo-dox A and lipo-dox B substituted at alcohol group showed similar anti-cancer effect as dox, but lipo-dox C and lipo-dox D substituted at amino group did not. As a result, the amino group of dox seems an important site for its cancer cell inhibition. Lipophilic property of lipo-dox A and lipo-dox B induced more accumulation in cells compared to parent drug. Therefore, the newly synthesized lipo-dox A and lipo-dox B would be a good candidate for anti-cancer agent.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Aspergillus itaconicus 유래 itaconic acid의 ester-monomer를 이용한 새로운 soft contact lens 소재 개발
유영현(Young-Hyun You),남주형(Joo-Hyeung Nam),김병길(Bieong-Kil Kim),김순복(Soon bok Kim),문익재(Ik-Jae Moon),김종필(Jong-Pil Kim),서영배(Young-Bae Seu) 한국생명과학회 2009 생명과학회지 Vol.19 No.4
본 연구는 itaconic acid로부터 합성한 새로운 soft contact lens 소재의 함수율과 산소투과도를 확인 하였다. Soft contact lens의 새로운 polymer소재 개발을 위하여 기본 monomer인 HEMA (2-hydroxyethyl methacrylate)와 가교제로서 EGDMA (ethylene glycol dimethacrylate) 그리고 A. itaconicus의 발효에 의해 생산된 itaconic acid로부터 얻어진 mono-ester 1과 di-ester 2를 새로운 첨가제로 사용하여 중합반응을 시도하였다. Soft contact lens의 새로운 폴리머 소재들은 HEMA와 mono-ester 1 또는 di-ester 2를 서로 다른 비율로 합성하여 함수율(water content)과 산소투과도(oxygen permeability)를 분석하였다. Polymer 형성을 위한 HEMA와 additive의 혼합에서 HEMA/mono-ester 1의 혼합물은 HEMA/di-ester 2 보다 함수율과 산소투과도가 뛰어 났으며 HEMA와 첨가제 mono-ester 1 (15%)를 이용한 중합의 경우, 제작된 soft contact lens의 함수율과 산소투과도는 각각 57.7%와 28.6 Dk로 좋은 값을 나타냈다. 새로운 소재를 사용하여 만든 soft contact lens의 함수율과 산소투과도는 우수하게 나타났다. In this study, we confirmed water content and oxygen permeability of new polymeric materials synthesized from itaconic acid used for soft contact lenses. In this study, we polymerized materials for soft contact lenses using HEMA (2-hydroxyethyl methacrylate), the based-monomer of soft contact lenses, EGDMA (ethylene glycol dimethacrylate) as a cross linkage agent, and the new additives mono-ester or di-ester derived from itaconic acid commercially produced by the fermentation of A. itaconicus. New polymer materials for contact lenses were synthesized with the mixture of HEMA and mono- or di-ester at different ratios and water content and oxygen permeability (Dk) was analyzed. In polymerizing HEMA and mono-ester (15%), the water content and oxygen permeability of contact lenses were found to be of good value at 57.7% and 28.6 Dk respectively. The mixture of HEMA and mono-ester is more excellent than HEMA/di-ester in regards to water content and oxygen permeability. The water content and oxygen permeability of soft contact lenses made by new polymeric materials were highly represented.