• 한국환경성돌연변이발암원학회:학술대회논문집
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• 한국환경성돌연변이발암원학회 2002년도 Molecular and Cellular Response to Toxic Substances
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• pp.177-177
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• 2002

• Bulletin of the Korean Chemical Society
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• 제28권4호
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• pp.513-514
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• 2007

• Bulletin of the Korean Chemical Society
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• 제30권3호
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• pp.745-748
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• 2009

• 한국생명과학회:학술대회논문집
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• 한국생명과학회 2007년도 제48회 학술심포지움 및 추계국제학술대회
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• pp.63.1-63.1
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• 2007

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• Bulletin of the Korean Chemical Society
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• 제20권5호
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• pp.551-555
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• 1999

11-Deoxydaunomycinone 15 and 10-fluoroanthracyclinone derivatives 9, 10 were obtained. Naphthalenone 4 prepared from 2-(2,4-pentadienyl)-1,3-dioxane 2 with methyl vinyl ketone and hydrolysis with HClO4 was condensed with phthalidesulfone 5 through Michael type reaction, and was converted to 7 by epoxidation. Epoxide 7 was transformed to trione 12 using reduction-oxidation or hydrofluorination process, and then to 15 by introducing several functional groups. Compound 8 obtained in the course of the reaction of epoxide 7 and HF/ Pyr was used for the synthesis of compounds 9, 10.

• KSBB Journal
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• 제20권4호
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• pp.311-316
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• 2005

EH의 catalytic nucleophile residue, His-Asp로 구성된 charge relay system, oxyanion hole 등의 EH 관련 conserved domain의 아미노산 공통 서열을 참고로 하여 G. westfalica megaplasmid로부터 putative EH를 선별할 수 있었다. Bioinformatics를 기반으로 스크리닝한 G. westfalica에 의한 라세믹 styrene oxide 기질에 대한 입체선택성 가수분해 반응에 있어 중요 반응 parameter들인, pH 및 온도 등이 초기 가수분해반응속도에 미치는 영향을 분석하고, 최적 회분식 반응조건을 결정하였다. 최적 반응조건인 pH 7, 반응 온도 $30^{\circ}C$, 생촉매량 40 mg의 조건에서 약 5시간 20분간 반응을 통해 20 mM 라세믹 기질로부터 광학순도 $100\%$ ee인 (S)-styrene oxide를 $36.5\%$의 수율로 얻을 수 있었다.

• 공업화학
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• 제19권5호
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• pp.491-496
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• 2008

해양 어류인 Mugil cephalus로부터 에폭사이드 가수분해효소(epoxide hydrolase, EH) 유전자를 PCR을 이용하여 클로닝하고, pColdI 및 pET-21b(+) 발현벡터에 삽입시켜 재조합 Escherichia coli 생촉매를 개발하여 각각에 대하여 가수분해 활성을 비교하였다. 재조합 E. coli 생촉매 $10mg\;dcw\;mL^{-1}$을 사용하여 20 mM 라세믹 styrene oxide를 입체선택적 가수분해를 한 결과, (R)-styrene oxide 기질에 대해서 입체선택성을 보였다. pET-21b(+)를 발현벡터로 사용하여 M. cephalus의 EH 유전자를 저온 발현시킨 재조합 E. coli 생촉매를 사용하여, 약 40 min 반응을 통해 광학순도 99% ee (enantiomeric excess) 이상인 (S)-styrene oxide를 최종 수율 24.5% (이론수율 50%)로 제조할 수 있었다.

• 대한약리학회지
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• 제32권2호
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• pp.233-241
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• 1996

Previous studies have shown that glucocorticoid suppresses microsomal epoxide hydrolase(EH) gene expression and that EH expression is altered during pregnancy. The effects of progesterone on the expression of rat EH and certain glutathione S-transferase(GST) genes were examined in this study. Northern RNA blot analysis revealed that progesterone was effective in increasing hepatic EH mRNA levels at 12 h to 48 h after treatment with a maximal 9-fold increase being noted at 12 h time point. Nonetheless, multiple daily treatment with progesterone rather caused minimal relative increases in EH mRNA levels. GST Ya and Yb1/2 mRNA levels were also transiently elevated at 12 h after progesterone treatment, followed by gradual decreases from the maximal Increases at day 1, 2 and 5 post-treatment. These changes in EH and GST mRNA levels were noted only at a relatively high dose of progesterone. Furthermore, immunoblot analyses showed that rats treated with progesterone for 5 days failed to show EH or GST induction, indicating that progesterone-induced alterations in EH and GST mRNA levels do not reflect bona fide induction of the detoxifying enzymes. Concomitant progesterone treatment of rats with the known EH inducers including ketoconazole and clotrimazole failed to additively nor antagonistically alter EH mRNA levels. In contrast, dexamethasone substantially reduced ketoconazole- or clotrimazole-inducible EH expression. These results showed that progesterone stimulates the EH, GST Ya and Yb1/2 gene expression at early times followed by marked reduction in the RNA levels from the maximum after multiple treatment and that the changes in mRNA do not necessarily reflect induction of the proteins.

• 대한약침학회지
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• 제20권3호
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• pp.207-212
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• 2017

Objectives: Study of the mechanisms involved in cancer progression suggests that cyclooxygenase enzymes play an important role in the induction of inflammation, tumor formation, and metastasis of cancer cells. Thus, cyclooxygenase enzymes could be considered for cancer chemotherapy. Among these enzymes, cyclooxygenase 2 (COX-2) is associated with liver carcinogenesis. Various COX-2 inhibitors cause growth inhibition of human hepatocellular carcinoma cells, but many of them act in the COX-2 independent mechanism. Thus, the introduction of selective COX-2 inhibitors is necessary to achieve a clear result. The present study was aimed to determine the growth-inhibitory effects of new analogues of chalcone epoxide as selective COX-2 inhibitors on the human hepatocellular carcinoma (HepG2) cell line. Methods: Estimation of both cell growth and the amount of prostaglandin E2 (PGE2) production were used to study the effect of selective COX-2 inhibitors on the hepatocellular carcinoma cell. Cell growth determination has done by MTT assay in 24 h, 48 h and 72 h, and PGE2 production has estimated by using ELYSA kit in 48 h and 72 h. Results: The results showed growth inhibition of the HepG2 cell line in a concentration and time-dependent manner, as well as a reduction in the formation of PGE2 as a product of COX-2 activity. Among the compounds those analogues with methoxy and hydrogen group showed more inhibitory effect than others. Conclusion: The current in-vitro study indicates that the observed significant growth-inhibitory effect of chalcone-epoxide analogues on the HepG2 cell line may involve COX-dependent mechanisms and the PGE2 pathway parallel to the effect of celecoxib. It can be said that these analogues might be efficient compounds in chemotherapy of COX-2 dependent carcinoma specially preventing and treatment of hepatocellular carcinomas.

• Korean Chemical Engineering Research
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• 제46권4호
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• pp.769-776
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• 2008

키랄성 말단기의 에폭사이드는 키랄중간체나 여러 출발물질로서 다양하게 이용되기 때문에 그 선택적인 합성법은 매우 유용하다. 본 연구에서는 염화코발트(II), 염화철(III) 및 질산아연(II)을 각각 함유한 키랄 코발트 살렌 촉매를 새로이 합성하고 그 특성을 평가하였다. 질량분석과 EXAF분석을 통하여 형성된 촉매 착체의 구조를 평가하였다. 합성한 촉매는 방향족 에폭사이드인 스타이렌 옥사이드와 페닐글리시딜 에테르의 속도차에 의한 비대칭 가수분해적 고리열림반응과 글리시틸부틸레이트의 합성반응에 적용하여 그 활성과 선택성을 조사하였다. 합성이 용이한 전이금속염함유 살렌착체 촉매는 물을 친핵체로 하는 라세믹 에폭사이드의 고리 열림을 통하여 99%ee 이상을 나타낼 정도의 매우 높은 광학선택성을 보였으며, 적은 양의 첨가로도 높은 활성을 보였다. 본 연구에서 적용한 촉매씨스템은 키랄 에폭사이드 및 1,2-디올 중간체의 제조에 매우 효과적이었다.