• 제목/요약/키워드: Chiral Separation

검색결과 194건 처리시간 0.022초

Enantioselective Determination of Cetirizine in Human Urine by HPLC

  • Choi, Sun-Ok;Lee, Seok-Ho;Kong, Hak-Soo;Kim, Eun-Jung;Parkchoo, Hae-Young
    • Archives of Pharmacal Research
    • /
    • 제23권2호
    • /
    • pp.178-181
    • /
    • 2000
  • In order to study the simultaneous determination of (+)- and (-)-cetirizine in human urine we have developed a chiral separation method by HPLC. A chiral stationary phase of $\alpha$$_1$-acidglycoprotein, the AGP-CSP was used to separate the enantiomers. The pH of the phosphate buffer, as well as the content of the organic modifier in the mobile phase, markedly affected the chromatographic separation of (+)- and (-)-cetirizine. A mobile phase of 10 m㏖/1 phosphate buffer (pH 7.0)-acetonitrile (95 : 5, v/v) was used for the urine assays. Ultraviolet absorption was monitored at 230nm and roxatidine was employed as the internal standard for quantification. (+)-Cetirizine, (-)-cetirizine and the internal standard were eluted at retention times of 12, 16, and 32 mins, respectively. The detection limit for cetirizine enantiomers was 400 ng/$m\ell$ of urine. A pharmacokinetic study was conducted with the help of 5 healthy female volunteers who were administered with a single oral dose of racemic cetirizine (20 mg). The peak area ratios provided by the cetirizine enantiomers were linear(r>0.997) over a concentration range of 2.5-200 ${\mu}g/ml$. The peak of the excreted cetirizine enantiomers appeared in the urine sample during the period of 1-2 hrs following the administration of the oral dose. The excreted level of (+)-cetirizine was slightly higher than (-)-cetirizine but the difference was not statistically significant. However, this method appears to have applications for enantioselective pharmacokinetic studies of racemic drugs.

  • PDF

크라운 에테르에서 유도된 키랄 컬럼을 사용한 레보티록신 나트륨 의약품의 광학순도 모니터링 (Monitoring of the Optical Purity for Levothyroxine Sodium in Pharmaceuticals Using Crown Ether Derived Chiral Columns)

  • 전소희;이원재
    • KSBB Journal
    • /
    • 제25권5호
    • /
    • pp.449-452
    • /
    • 2010
  • 크라운 에테르로부터 유도된 키랄고정상에서 역상용매를 이동상으로 사용하여 국내외에서 시판되고 있는 광학이성질체 의약품인 레보티록신 나트륨의 광학순도 측정을 위한 새로운 직접적인 광학분리 분석법을 개발하여 매우 좋은 결과를 얻었다 ($\alpha$ = 2.15, Rs = 4.05). 시판하고 있는 레보티록신 나트륨의 광학순도를 키랄고정상을 이용하여 직접적인 광학분리방법으로 측정하는 실험은 현재까지 한 편의 연구결과 외에는 보고되어 있지 않는데 [4] 본 연구에서 새롭게 개발한 전처리과정과 HPLC 분석조건을 이용하여 현재 국내외에서 판매되고 있는 레보티록신 나트륨 주성분의 의약품 정제의 광학순도를 측정하였다. 레보티록신 나트륨의 광학순도를 측정한 광학분리 실험결과에서 하나의 제품을 제외하고는 99% 이상의 높은 광학순도를 보여주고 있음을 확인할 수 있었다. 본 연구의 편리하고 용이한 신규 광학분리 분석법이 국내외에서 상용되는 레보티록신 나트륨 제품의 품질 확인과 양질의 키랄의약품을 개발하고 제품을 관리하는데 매우 도움이 되리라 기대한다.

Determination of methamphetamine and amphetamine enantiomers in human urine by chiral stationary phase liquid chromatography-tandem mass spectrometry

  • Sim, Yeong Eun;Ko, Beom Jun;Kim, Jin Young
    • 분석과학
    • /
    • 제32권5호
    • /
    • pp.163-172
    • /
    • 2019
  • Methamphetamine (MA) is currently the most abused illicit drug in Korea and its major metabolite is amphetamine (AP). As MA exist as two enantiomers with the different pharmacological properties, it is necessary to determine their respective amounts in a sample. Thus a chiral stationary phase liquid chromatography-tandem mass spectrometric (LC-MS/MS) method was developed for identification and quantification of d-MA, l-MA, d-AP, and l-AP in human urine. Urine sample ($200{\mu}L$) was diluted with pure water and purified using solid-phase extraction (SPE) cartridge. A $5-{\mu}L$ aliquot of SPE treated sample solution was injected into LC-MS/MS system. Chiral separation was carried out on the Astec Chirobiotic V2 column with an isocratic elution for each enantiomer. Identification and quantification of enantiomeric MA and AP was performed using multiple reaction monitoring (MRM) detection mode. Linear regression with a $1/x^2$ as the weighting factor was applied to generate a calibration curve. The linear ranges were 25-1000 ng/mL for all compounds. The intra- and inter-day precisions were within 3.6 %, while the intra- and inter-day accuracies ranged from -5.4 % to 11.8 %. The limits of detection were 2.5 ng/mL (d-MA), 3.5 ng/mL (l-MA), 7.5 ng/mL (d-AP), and 7.5 ng/mL (l-AP). Method validation parameters such as selectivity, matrix effect, and stability were evaluated and met acceptance criteria. The applicability of the method was tested by the analysis of genuine forensic urine samples from drug abusers. d-MA is the most common compound found in urine and mainly used by abusers.

Liquid Chromatographic Resolution of Both $\pi$-Acidic and $\pi$-Basic Analytes on a Chiral Stationary Phase Derived from (S)-Tyrosine

  • 현명호;민정식
    • Bulletin of the Korean Chemical Society
    • /
    • 제17권12호
    • /
    • pp.1117-1123
    • /
    • 1996
  • Chiral recognition models for resolving π-basic N-acyl-α-(1-naphthyl)alkylamines and π-acidic N-(3,5-dinitrobenzoyl)-α-amino alkyl esters on a (S)-tyrosine-derived chiral stationary phase (CSP) containing both π-basic and π-acidic interaction site have been proposed. In the models, the CSP was supposed to interact with the analytes through the π-π interaction between the 3,5-dinitrophenyl or the 3,5-dimethylphenyl group of the CSP and the 1-naphthyl or the 3,5-dinitrophenyl group of the analyte, and through the hydrogen bonding interaction between the appropriate N-H hydrogen of the CSP and the appropriate carbonyl oxygen of the analyte. In this instance, the alkyl substituent of the pertinent enantiomer of the analyte was found to intercalate between the adjacent strands of the bonded phase and consequently control the trends of the separation factors.

Distribution of (-)-Yatein in Cupressaceae Family Analysed by High Performance liquid Chromatography

  • Hwang, Gwi-Seo;Phuong, Nguyen-Thi;Park, Kyung-Rae;Kim, Young-Ho;Kim, Kyeong-Ho;Kang, Jong-Seong
    • Archives of Pharmacal Research
    • /
    • 제27권1호
    • /
    • pp.35-39
    • /
    • 2004
  • The method for the chiral analysis of (-)-yatein was developed and the distribution of this component in the plants of three genera like Juniperus, Thuja and Chamaecyparis belonging to Cupressaceae family was examined. The chiral analysis of (-)-yatein from the plants was carried out by high performance liquid chromatography on (R,R)-Whelk-O1 column using 81 v/v% methanol as mobile phase. The yatein content in the leaves of Juniperus was the highest in compare with that of the other two genera, providing the possibility of the chemical discrimination of the plants in Juniperus from the other plants in the Cupressaceae family. In general, the yatein content in the leaves was much higher than that in the twigs. This method could be applied for the quality control of (-)-yatein in the plants belonging to Cupressaceae family.

Preparative Chromatographic Separaction: Simulated Moving Bed and Modified Chromatography Methods

  • Yi Xie;Koo, Yoon-Mo;Nien-Hwa Linda Wang
    • Biotechnology and Bioprocess Engineering:BBE
    • /
    • 제6권6호
    • /
    • pp.363-375
    • /
    • 2001
  • Chromatography has been method of choice for the separation complex biologi-cal mixtures fro analytical purpose, particularly for the last fifty years. Its use has recently been extended to preparative separation where the productivity relative to the amount of resin and sol-vent used is a matter of concern. To overcome the inherent thermodynamic inefficiency of batch chromatography, as exemplified by the partial temporal usage of the resin and dilution of the product with the solvent, chromatography has been continually modified by separation engineers. Column switching and recycling represnet some of the process modifications that have brought high productivity to chromatography. Recently, the simulated moving bed (SMB) method, which claims a high separation efficiency based on counter-current moving bed chromatography. has be-come the mainstay of preparative separation, especially in chiral separation. Accordingly, this pa-per reviews the current status of SMB along with several chromatographic modification, which may be helpful in routine laboratory and industrial chromatographic practices.

  • PDF

Liquid Chromatographic Resolution of Tocainide and Its Analogues on a Doubly Tethered Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

  • Kim, Hee-Jin;Choi, Hee-Jung;Hyun, Myung-Ho
    • Bulletin of the Korean Chemical Society
    • /
    • 제31권3호
    • /
    • pp.678-682
    • /
    • 2010
  • A doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were applied to the liquid chromatographic resolution of racemic tocainide, an antiarrhythmic agent, and its analogues. The chiral recognition efficiency of the doubly tethered CSP for tocainide and its analogues was generally greater than that of the corresponding singly tethered CSP especially in terms of the resolution ($R_S$). The resolution of tocainide and its analogues on the doubly tethered CSP were dependent on the content and the type of the organic and acidic modifiers in aqueous mobile phase and the column temperature. Especially, the retention behaviors of analytes on the doubly tethered CSP with the variation of the content of organic modifier in aqueous mobile phase were opposite to those on the corresponding singly tethered CSP and these opposite retention behaviors were rationalized by the lipophilicity differences of the two CSPs.

고체 담체에 고정화된 키랄리간드의 비대칭 촉매반응에의 응용 (Application of Chiral Ligands Heterogenized over Solid Supports on Enantioselective Catalysis)

  • 이광연;카테카 라울;김건중
    • 공업화학
    • /
    • 제17권6호
    • /
    • pp.565-574
    • /
    • 2006
  • 광학순도가 높은 이성체의 응용은 최근 들어 크게 증가되고 있는 추세이다. 여러 가지 방법 중에서도 비대칭 촉매합성반응을 통하여 선택적으로 순수한 광학이성체를 합성하는 것이 가장 매력적인 방법이다. 특히 키랄화합물을 합성하는 비대칭촉매반응에 있어서는 가격이 비싼 촉매를 소량 사용하면서도 활성이나 광학선택성 및 촉매수명을 높이도록 하는 조건이 매우 중요하게 대두된다. 활성이 큰 키랄촉매를 고정화시키면 반응 후에 반응혼합물을 여과법으로 쉽게 제거할 수 있다는 등의 취급상 용이한 점을 제공한다. 키랄촉매반응에서 생성물의 광학선택성을 향상시키고 여러 번 촉매를 재사용할 수 있도록 하려는 다양한 방법이 연구되고 있다. 본 총설에서는 여러 종류의 광학선택적인 불균일촉매에 관한 연구의 현황과 제한점 등을 주로 다루었다.

감광성 도판트를 이용한 풀컬러 구현 가능 반사형 콜레스테릭 액정 (Full color reflective cholesteric liquid cystal using photosensitive chiral dopant)

  • 박서규;조희석;권순범;김정수;레즈니코프
    • 한국전기전자재료학회:학술대회논문집
    • /
    • 한국전기전자재료학회 2007년도 추계학술대회 논문집
    • /
    • pp.394-395
    • /
    • 2007
  • In order to make full color cholesteric displays, color filter-less R, G, B sub-pixel structured cholesteric LC cells have been studied. To make R, G, B colors, UV induced pitch variant chiral dopant was added to cholesteric LC mixtures. The concentration of the photo-sensitive chiral dopant was adjusted so that the initial state showed blue color and the color was changed from blue to green and red with increase of UV irradiation to the cholesteric cells. To prevent the mixing of R, G, B reflective sub-pixel liquid crystals, separation walls were formed using negative photo resister in boundary area between sub-pixels. Through the optimization of the material concentrations and UV irradiation condition, vivid R, G, B colors were achieved.

  • PDF

Preparation of a New Chiral Stationary Phase Based on (2S,3S)-O,O'-Bis-(10-undecenoyl)-N,N'-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol and Its Application

  • Hyun, Myung Ho;Boo, Chang-Jin;Choi, Hee-Jung;Kim, Yun-Kyoung;Kang, Bu-Sung;Ha, Hyun-Ju;Choi, Min-Ki;Tan, Guang-Hui
    • Bulletin of the Korean Chemical Society
    • /
    • 제27권11호
    • /
    • pp.1769-1774
    • /
    • 2006
  • A new liquid chromatographic chiral stationary phase based on (2S,3S)-O,O'-bis-(10-undecenoyl)-N,N'-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol was prepared starting from (2R,3R)-1,4-bis(benzyloxy)-2,3-butanediol. The new chiral stationary phase was applied to the resolution of racemic anilide derivatives of N-acetyl-a-amino acids, 1,1'-bi-2-naphthol and 3,3'-diaryl-1,1'-bi-2-naphthols. The CSP was also applied to the resolution of some chiral drugs including a diuretic, bendroflumethiazide, and non-steroidal anti-inflammatory agents such naproxen and alminoprofen. In every case, the chiral recognition efficiency of the new CSP was quite excellent.