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研究生:趙素慧
研究生(外文):Su-Hui Chao
論文名稱:光敏感性藥物研究第壹部分鈣離子阻斷劑光分解反應研究第貳部分非固醇類抗發炎藥物光分解產物及其抗發炎活性
論文名稱(外文):Photosensitivity drugs(I) Photodegradation of calcium channel blockers(II) Photoproducts of NSAIDs and their anti-inflammatory activities
指導教授:吳安邦
學位類別:博士
校院名稱:臺北醫學大學
系所名稱:藥學研究所
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2007
畢業學年度:95
語文別:中文
論文頁數:106
中文關鍵詞:光敏感性藥物鈣離子阻斷劑非固醇類抗發炎藥物光分解產物
外文關鍵詞:Photosensitivity drugsCalcium channel blockersNSAIDsPhotoproducts
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光敏感性是藥物常見的不良影響,本研究第一部份為尼卡迪平的光分解反應,尼卡迪平暴露於汞燈下,以LC/MS鑑定共8個光分解產物,主產物為4-(3''-硝基苯基)吡啶衍生物(NIC-7)。尼卡迪平於照光後進行一系列的硝基還原反應,並提出其可能的反應途徑。

研究第二部份目的是選擇特定之非固醇類抗發炎藥物(氟白普洛芬與吲哚美洒辛)在醇類溶媒中以汞燈照射探討其光解情形,以GC/MS與LC/MS進行其光解產物結構之鑑定,並檢查吲哚美洒辛及其產物一些藥理作用。總計以GC/MS與LC/MS光譜分析氟白普洛芬與吲哚美洒辛於甲醇溶媒中之光分解,各鑑定出10個與4個光解產物,並進而推測其反應途徑。在藥理研究方面,吲哚美洒辛比較其所衍生之光解產物,具有最強的氫氧自由基與黃嘌呤氧化酵素抑制活性,IC50各為 65 µM與86 µM。此外,吲哚美洒辛甲基酯衍生物(IN-3)其在LPS刺激RAW 264.7巨噬細胞誘導發炎的實驗模式中具有優於IN的抑制NO及PGE2生成與iNOS及COX-2蛋白表現的能力,類似一般NSAIDs的作用。對HL-60之細胞毒殺效果是以MTT法檢驗,結果顯示HL-60細胞毒殺IC50為36.9 g/mL,效果強於IN。再者,由生化檢驗發現IN-3會引起HL-60細胞凋亡、DNA 裂解,並增強PARP與pro-caspase 3的裂解作用,以上結果支持光解產物IN-3具有優於母藥吲哚美洒辛的抗發炎(LPS刺激RAW 264.7巨噬細胞)及細胞毒殺(HL-60)效果。
Photosensitivity is a commonly adverse effect of drugs. The purpose of the first part of this study is focus on the photodegradation of nicardipine. When nicardipine was exposed to the Hg lamp, eight photoproducts of nicardipine were identification by LC/MS. The main degraded product was a pyridine analogue (NIC-7). Nicardipine apparently undergoes a series of nitro group photo-reduction pathways under irradiation leading to a complex formation of mainly the reduced products. A reaction scheme of nicardipine was proposed.

The second part, gives a study on the photochemical behavior when NSAIDs (flurbiprofen and indomethacin) in alcoholic solvents are exposed to Hg lamps. GC/MS and LC/MS were applied to determine the structure of photoproducts. In addition, some pharmacological effects were also examined. In total, ten and four photoproducts derived from flurbiprofen and indomethacin methanolic samples, respectively, were identified by GC/MS and LC/MS. Furthermore, the reaction schemes of flurbiprofen and indomethacin in methanol are proposed. As to the study of pharmacological effects, results suggested that among all the related photoproducts, Indomethacin stand out and showed the strongest hydroxyl radical-scavenging effect with an IC50 of 65 µM and the strongest xanthine oxidase inhibitory effect with an IC50 of 86 µM. We also found that the methyl ester derivatives of indomethacin (IN-3) could more-potently inhibit PGE2 and NO production and iNOS and COX 2 protein expression from LPS-stimulated RAW 264.7 cells than indomethacin, similar to the effect of a typical NSAID. The cytotoxic effects of the test samples were measured using the MTT assay. The results showed that IN-3 with an IC50 value maintained at 36.9 ?慊/mL for 12 h that exhibited stronger cytotoxicity than indomethacin in HL-60 cells. Moreover, IN-3 caused apoptotic bodies, DNA fragmentation, and enhanced PARP and pro-caspase 3 degradation in HL-60 cells as determined by a series of biochemical analyses. The above results indicated that the photoproduct, IN-3, had stronger anti-inflammatory in LPS-stimulated RAW 264.7 cells and cytotoxicity effects in HL-60 cells than the parent drug, indomethacin.
目 錄
中文摘要.......................................... vii
英文摘要.......................................... viii
縮寫表............................................ ix
緒論.............................................. 1

第壹部份 尼卡迪平光分解反應研究

第一章 研究背景及目的............................ 2
(一) 研究之背景.................................... 2
1.藥物光過敏反應及機轉.......................... 2
2.鈣離子阻斷劑光分解反應研究.................... 4
(二) 研究之動機及目的.............................. 11
第二章 實驗材料及方法............................ 14
(一) 實驗材料...................................... 14
(二) 實驗方法...................................... 14
第三章 實驗結果與討論............................ 16

第貳部份 非固醇類抗發炎藥物光分解產物及其抗發炎活性

第一章 研究背景及目的............................. 22
(一) 研究之背景..................................... 22
1. NSAIDs藥理作用................................. 22
2. NSAIDs的光過敏反應研究......................... 23
3. NSAIDs的光分解與產物結構....................... 25
4. NSAIDs常見的不良反應........................... 26
5. NSAIDs的新適應症與發展方向..................... 27
(二) 研究之動機及目的............................... 28
1. 以GC/MS研究FB光解產物與機轉.................... 28
2. 以LC/MS研究IN光解產物與機轉.................... 30
3. IN光解產物藥理作用探討......................... 34
第二章 實驗材料及方法............................. 43
(一) 以GC/MS研究FB光解產物與機轉.................... 43
(二) 以LC/MS研究IN光解產物與機轉.................... 44
(三) IN光解產物藥理作用探討......................... 45
第三章 實驗結果與討論............................. 50
(一) 以GC/MS研究FB光解產物與機轉.................... 50
(二) 以LC/MS研究IN光解產物與機轉.................... 57
(三) IN光解產物藥理作用探討......................... 60
1. IN光分解產物分離............................... 60
2. IN光分解產物對•OH清除與XO活性抑制之抗氧化效果.. 61
3. IN光分解產物對RAW 264.7以LPS誘導發炎之抑制效果. 63
4. IN光分解產物引發HL-60之細胞凋亡效果............ 64
結論................................................ 69
參考文獻............................................ 70
附錄................................................ 84
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