TWI321570B - Peptide compounds,and method of measuring sulfur compound and ammonia therewith - Google Patents
Peptide compounds,and method of measuring sulfur compound and ammonia therewith Download PDFInfo
- Publication number
- TWI321570B TWI321570B TW090132419A TW90132419A TWI321570B TW I321570 B TWI321570 B TW I321570B TW 090132419 A TW090132419 A TW 090132419A TW 90132419 A TW90132419 A TW 90132419A TW I321570 B TWI321570 B TW I321570B
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- Prior art keywords
- compound
- peptide
- ammonia
- sulfur
- detecting
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1321570 六、發明說明： 【發明所屬之技術領域】 本發明係有關於胜肽化合物，特別是有關於對肝硬化 患者呼氣中之硫類化合物及氨具有高键結敏感度和鍵結強 度，可用於檢測硫類化合物、氨及肝硬化等疾病狀況之胜 f 肽化合物。本發明亦有關於利用上述胜肽化合物檢測硫類 化合物及氨之方法。 Φ 【先前技術】 在哺乳動物的嗅覺系統中，位於鼻黏膜上具有嗅覺接 受蛋白嵌於細胞膜上，此嗅覺接受蛋白可以與氣體分子反 應後，將訊息經由一連串的生化反應傳至大腦的嗅覺區判 斷味道種類。嗅覺接受蛋白對不同的氣體分子具有不同的 鍵結位置，此完全取決於其氨基酸序列與所形成之立體結 構；本發明係以此為契子進而推論不同的胜肽序列對不同 的氣體分子或化合物具有不同的鍵結能力。即配合不同感 • 測功能，再設計不同的胜肽作為接受膜，而達到檢測特定 化合物之目的。 在許多疾病狀態下，如肝硬化、肝病、牙齦炎等情況， 體内的硫類化合物會偏高；腎臟病、尿毒症、胃潰瘍等情 況，體内的氨含量會偏高，因此可藉由測量體内或呼出氣 體中之硫類化合物及氨的含量以判斷是否有此類疾病。另 外，海產如魚類、貝類的腐壞亦會釋放出氨，因此本發明 亦可應用於海產新鮮度的檢測。相同地，本發明亦適用於 空氣或水中硫類化合物及氨含量之檢測，進而判斷是否有 4 1321570 空氣污染或水質污染的情況。 【發明内容】 本發明提供一種胜肽化合物，其對硫類化合物及氨具 有高敏感度及高鍵結強度，適用於硫類化合物及氨之檢 測。本發明之胜肽化合物特別適用於檢測肝硬化患者呼氣。 本發明亦提供以上述胜肽化合物檢測硫類化合物及氨 之方法，包括下列步驟：令一待測物質與一感測元件接觸， 此感測元件上覆被有前述之胜肽化合物；處理所得之信籲 號；以及將信號與一資料庫比對，以定義待測物質中的硫 類化合物及氨的存在。 本發明亦提供一檢測硫類化合物及氨之裝置，包括一 個或多個感測元件，其上覆被有前文所述胜肽化合物，及 一信號處理單元耦接於該感測元件用以產生一信號。 本發明之胜肽序列對於硫類化合物及氨具有高敏感度 及高鍵結強度的特性，利用此胜肽序列或含有此胜肽之化 合物作為與嗅覺閥值低的硫類化合物及氨反應或檢測的物 * 質，運用於感測器的檢測上，作為檢測硫類化合物及氨之 工具，具有提高敏感度及低濃度物質檢測適用性等特質。 為了讓本發明之上述和其他目的、特徵、和優點能更 明顯易懂，下文特舉較佳實施例，並配合所附圖示，作詳 細說明如下： 【實施方式】 5 1321570 為達以設計胜肽檢測硫類化合物之目的，可經由蛋白 質之二級結構分析胜肽序列特性或利用蛋白質之三級結構 模擬與目標分子之鍵結位置或根據檢測物質之物性與化性 任意設計氨基酸之組合，進行胜肽序列設計，再以人工方 式加以合成；所得到之胜肽化合物配合感測元件或晶片將 訊號輸出，可用於硫類化合物’即含有-R-SH功能基團之 '化合物，其中R為烷基基團（Alkyl group)或芳香基團（Aryl group)，而對於含有氨（ammonia)、二曱基硫 φ (dimethylsulfide)、與二曱基硫：H20 = 1 : 1 (dimethylsulfide:H20 = 1:1)等化合物的檢測則是特別靈敏。 本發明之胜肽序列係擇自由下列族群中： 序列辨識號 1 : Gly-Asn-Thr-Tyr-Asp ; 序列辨識號 2 : Glu-Gly-Asn-Thr-Tyr-Asp ; 序列辨識號 3 : Lys-Phe-Lys-Glu-Val ; 序列辨識號 4 : Glu-Ser-Lys-Val-Tyr ; 序列辨識號 5 : Asp-Val-Asn-Tyr-Gly-Asn ;及 鲁 序列辨識號 6: Lys-Phe-Lys-Glu-Val-Thr-Arg-Glu-Asn。 上述胜肽序列可視需要在其羧酸端及/或氨基端加上 一或複數個修飾基團，此修飾基團可為胺基酸或其它功能 基團，胺基酸如：胺基丙酸、精胺酸、天門冬醯胺、天門 冬胺酸、半胱胺酸、麩胺酸醯胺、麩胺酸、甘胺酸、組織 胺酸、異白胺酸、白胺酸、離胺酸、甲硫胺酸、苯胺基丙 酸、脯胺酸、絲胺酸、息寧胺酸、色胺酸、酪胺酸、及纈 胺酸；功能基團則可擇自-COOH、-NH2、-CHO、_OH、或 -SH。 6 1321570 本發明之以胜肽化合物檢測硫類化合物及氨之方法， 係利用前文所述之胜肽化合物可與硫類化合物及氨所產生 鍵結作用的特性’而達到檢測樣本内硫類化合物及氨、其 液相、或其揮發性氣體之含量的目的。第1圖係本發明以 胜肽化合物檢測硫類化合物及氨之方法的淹程圖，包括下 列步驟：以一感測元件感測一待測物質，此感測元件上覆 被有前述之胜肽化合物；處理所得之信號；以及將信號與 一已建立的資料庫比對，以定義待測物質中的硫類化合物 及氣之含量。硫類化合物在此是指具有功能基圑之籲 化合物，其中R為烷基基團（Alkyl group)或芳香基團（Aryi group)，例如具二甲基硫、二曱基硫：h2〇 = 1 : 1、及氨基 團之化合物。上述方法包括：在一感測元件上，固定前文 所述之胜肽化合物，使此感測元件與一樣本接觸，藉由偵 測此胜狀化合物與硫類化合物及氨的結合，以檢測該樣本 所含之硫類化合物及氨之存在。其中可作為感測器者如化 學感測器、生物感測器或電子鼻的接受器、1物晶片，其 感測元件之傳導器（transducer)可為壓電石英晶體# (piezoelectric quartz crystal)、表面聲波（surface ac〇ustic wave)、電化學(electrochemical)、光纖(fiber 〇ptic)、表面電 漿共振（surface plasmon resonance) '金屬氧化物半導體 (metal oxide semiconductor)。壓電晶體是一項近年頗受重 視的檢測工具之一 ’其接受益具有一石英晶體，其上覆被 以前述之胜肽化合物，當胜肽化合物與硫類分子反應時， 質量的改變便會影響石英晶體的頻率，故反應時的強度便 可根據石英晶體的頻率改變來指示。而本發明之胜肽序列 7 1321570 對硫類化合物及氨具有極佳的鍵結敏感度及鍵結強度，在 檢測硫類化合物及氨上提供極佳的敏感度。本發明之方法 中，受測之樣本可為氣體、液體或固體，舉例來說，如空 氣、水、海產、動物或人體的血液、尿液及呼氣等。 本發明檢測硫類之方法可應用的範圍相當廣泛，例如 可藉由檢測如，呼氣、血液或尿液等樣本中所含的硫類含 量而判斷其疾病狀態，此類疾病的例子有：肝硬化、肝病、 牙齦炎等症狀。本發明檢測氨之方法可應用的範圍，例如 φ 可藉由檢測如，呼氣、血液或尿液等樣本中所含的氨含量 而判斷其疾病狀態，此類疾病的例子有：腎臟病、尿毒症 及胃潰瘍。特別是肝硬化可直接藉測量患者呼出氣體的硫 類及氨化合物的濃度變化而檢測。本發明亦適用於海產新 鮮度檢測、空氣污染之檢測、及水質檢測。 本發明之檢測硫類化合物及氨之裝置，包括一感測元 件，其上覆被有前文所述胜肽化合物，及一信號處理單元 轉接於該感測元件用以產生一信號。上述感測元件可為前 • 述應用各種物理、化學形式應用之傳感器或生物晶片。 為了進一步闡明本發明之方法、特徵、和優點，以下 以電子鼻感測器，提出實施例作詳細說明如下： 發明人以嗅覺接受蛋白的立體結構為板模，利用電腦 軟體Insight II模擬與肝硬化患者呼氣作用的可能位置的胜 肽，再根據氨基酸之特性加以修飾此胜肽序列，透過以電 腦模擬設計對硫類化合物具有專一性、高靈敏度反應之胜 肽序列，將之作為電子鼻的接受膜，進而用於檢測具硫類 功能基團之化合物。電子鼻的傳導器（transducer)是採用 8 1321570 12MHz 壓電石英晶體（pjez〇eiectric quartz cryStai)，再將設 計之胜肽覆被於石英晶體上，以電子鼻系統分析對硫類化 合物之反應。 【實施例】 製備例1 :胜肽之合成 本發明胜肽可以人工合成方式取得，如固相合成（solid phase synthesis)、液態胜肽合成（HqUid peptide synthesis)、 酵素合成（enzymtic synthesis)、或DNA重組技術 (recombinant DNA technology)。本實施例依據固相合成， 以Wang resin為樹脂，F-moc為保護基，經由胜肽合成儀 (Apply Biosystems，432A Peptide Synthesizer，USA)合成。 製備例2 :修飾與覆被胜肽於壓電晶體金電極表面 設計胜肽序列時，利用硫可與金形成穩定的共價鍵， 利用Traut氏試劑（Traut’s reagent)將胜肽硫化後，依胜肽的 溶解度以適當的有機溶劑稀釋，覆被在具有金電極的壓電 晶體表面上。胜肽之覆被方式是取2-4μ 1的溶液覆蓋於壓 電晶體之金電極上’於45°C反應後，偵測頻率下降值至 15000〜20000 Hz左右即可’但有些分子性質較特殊則依反 應結果調整覆被量。 製備例3 :揮發性氣體之製備 將試藥級二曱基胺、氨、丙酮、丁酸、及曱醛等化合 1321570 物各別溶於揮發性有機溶液5 m卜置於120 ml的密閉血清 瓶中’平衡5天至上部空間氣體達飽和蒸氣壓，由溶液的 濃度及飽和蒸氣壓值可換算得知上部空間氣體的濃度。依 測試所需’可利用上部空間氣體再稀釋使用或直接抽取分 析。 實施例1 :胜肽序列1-6 (序列辨識號1-6)對揮發性 氣體的反應 • 將胜肽序列1 (序列辨識號1)覆被於電子鼻壓電晶 體’藉助電子鼻分析系統（Smart Biotechnology Co., Ltd., Taipei，Taiwan)，對二曱基硫、二曱基琉：Η20 = 1 : 1及氨 等三種硫類揮發性氣體，及其它上述之化合物的上部空間 揮發氣體個別進行反應，用於電子鼻分析之氣體約為5 mg/1左右，比較反應之專一性及靈敏度。 此六個胜肽覆被於電子鼻壓電晶體上的量，根據 Sauerbrey equation (Sauerbrey, 1959)，壓電晶體頻率下降值 • 與其上質量的改變成正比，故以胜肽覆被後之頻率下降值 (Hz)表示覆被量大小。本實施例中，胜肽序列1至6 (序列 辨識號1-6)之覆被量列於表1 : 表1 胜肽序列 1 (序列辨 識號1) 胜肽序列 2 (序列辨 識號2) 胜肽序列 3 (序列辨 識號3) 胜肽序列 4 (序列辨 識號4) 胜肽序列 5 (序列辨 識號5) 胜肽序列 6 (序列辨 識號6) 胜肽序 6442 31 4890 8750 883 1148 1321570 列覆被 量（Hz) 胜肽序列1至6 (序列辨識號1-6)對二曱基硫、氨、 丙嗣、丁酸、及甲搭等有機揮發性氣體反應靈敏度之比較 則如第2圖所示。由第2圖中可以看出胜肽序列1及2 (序 列辨識號1及2)對二曱基硫、二甲基硫：H20 = 1 : 1、及 氨的反應最明顯、專一性最佳，其中對氨的反應又特別顯 著，而對其他的有機揮發性氣體反應很差，顯示胜肽序列 1及2 (序列辨識號1及2)極適合用來檢測硫類及氨化合 物。胜肽序列3-6 (序列辨識號3-6)對二曱基硫：H20= 1 : 1及氨的反應最明顯、專一性最佳，顯示胜肽序列3-6 (序 列辨識號3-6)極適合用來檢測二曱基硫：H20 = 1 : 1及 氨等化合物 實施例2 :胜肽序列1-6 (序列辨識號1-6)對健康人 及肝硬化患者呼氣之反應 肝硬化病人之啤氣含有多量的含硫化合物及氨。將在 中國醫藥學院收集的63個肝硬化病人呼氣氣體以及31個 健康人呼氣氣體藉由本發明之胜肽序列1-6 (序列辨識號 1 -6 )，分別覆被於六個壓電晶體上，配合電子鼻分析系統 進行反應，比較肝硬化病人與健康人之呼氣氣體對與本發 明之胜肽序列的反應。反應結果由統計軟體 STATGRAPHICS Plus分析。利用本發明之胜肽序列進行呼 1321570 氣分析之結果如下所述：63位肝硬化患者中有60位（95.24 %)被判定為肝硬化患者，3位（4.76 %)被判定為正常；31 位健康人中有3位（9.68 %)被判定為肝硬化患者，28位 (90.32 %)被判定為正常；經由統計，本分析方法的準確度 高達93.62 %。由此可見本發明之胜肽化合物對於肝硬化患 者之判定確有其應用上的價值。 本發明亦適於以類似方法加以收集關於其它會導致呼 φ 氣中硫類化合物及氨上升之疾病，如腎臟病、尿毒症、肝 病、牙齦炎及胃潰瘍等症狀之資料，建立對比資料庫，進 而應用於上述症狀的判定上。 雖然本發明已以較佳實施例揭露如上，然其並非用以 限定本發明，任何熟習此技藝者，在不脫離本發明之精 神和範圍内，當可作些許之更動與潤飾，因此本發明之 保護範圍當視後附之申請專利範圍所界定者為準。
12 1321570 【圖式簡單說明】 第1圖：本發明以胜肽化合物檢測硫類化合物及氨 之方法的流程圖；及 第2圖：胜肽序列卜6 (序列辨識號1_6)對各種有 機揮發性氣體反應靈敏度之比較圖。 【主要元件符號說明】
13 1321570 序列表 <110>財團法人工業技術研究院 <120>胜肽化合物及使用其檢測硫類化合物及氨之方法 <140> 90132419 <141〉90 年 12 月 26 日 <160> 6 <210> 1 <211> 5 <212>胺基酸 <213>人工序列 <400> 1
Gly Asn Thr Tyr Asp 5 <210〉 2 <211> 6 <212>胺基酸 <213>人工序列 <400> 2
Glu Gly Asn Thr Tyr Asp 1321570 1 5 <210> 3 <211> 5 <212>胺基酸 <213>人工序列 <400>3
Lys Phe Lys Glu Yal 5 <210> 4 <211> 5 <212>胺基酸 <213>人工序列 <400>4
Glu Ser Lys Val Tyr 1 5 <210> 5 <211> 6 <212>胺基酸 <213>人工序列 <400>5
Asp Val Asn Tyr Gly Asn 1 5 <210〉 6 1321570 <211> 9 <212>胺基酸 <213>人工序列 <400>6
Lys Phe Lys Glu Val Thr Arg Glu Asn 1 5
3
Claims (1)
1^^1570
七、申請專利遽
1. 一種用於檢測疏類化合物及氨之胜肽化合物， 係 為 Glu-Gly-Asn-Thr-Tyr-Asp (序列辨識號 2)之胜肽 序列。 2 ·種以胜狀化合物檢測硫類化合物及氧之方法， 包括： 以一感測元件感測一待測物質，該感測元件上覆被 有至少一種以上述之胜肽化合物； 處理所得之信號；及 將該信號與一資料庫比對，其中該硫類係具有-R-SH 功能基團之化合物，其中R為烷基基團或芳香基團； 又該胜肽化合物係為： Glu-Gly-Asn-Thr-Tyr-Asp (序列辨識號 2)之胜肽 序列。 3.如申請專利範圍第2項所述之以胜肽化合物檢測 硫類化合物及氨之方法，其中該感測元件之傳導，器係一 壓電石英晶體、表面聲波、電化學、光纖、表面電漿共 振或金屬氧化物半導體。 4·如申請專利範圍第2項所述之以胜肽化合物檢測 硫類化合物及氨之方法，其中該感測元件係一生物晶片。 5. 如申請專利範圍第2項所述之以胜肽化合物檢測 硫類化合物及氨之方法，其中該硫類係擇自下列族群 中：二曱基硫、二曱基硫：H2〇 = 1 : 1。 6. 如申請專利範圍第2項所述之以胜肽化合物檢測 ΓΓ:及氨=法’其中待測物質係擇自下列族群 :.水、二氣、動物呼氣、動物血液、動物尿液、及海 度0 7. 種檢測硫類化合物及氨❹ 件’其上覆被有至少—種以上胜肽化合物，一 心號處理單4接於該感測元件用以產生—信號，其中 之該胜肽化合物係為： GluGly-Asn-Thr-Tyr-Asp (序列辨識號 之胜肽 序列。 〃 8.如中請專利範圍第7項所述之檢測硫類化合物及 氰之裴置，其中該感測元件係—生物晶片。 9.如申請專利範圍第7項所述之：測硫類化合物及 風：裝置，其可用於測量一人類之呼氣；上述裝置更包 括v、有健康人及肝硬化病人呼氣氣體對該胜肽化合物 反應之資料庫，用以與所測得之資料比對。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW090132419A TWI321570B (en) | 2001-12-26 | 2001-12-26 | Peptide compounds,and method of measuring sulfur compound and ammonia therewith |
| US10/321,652 US7267989B2 (en) | 2001-12-26 | 2002-12-18 | Method and device for measuring sulfur compound and/or ammonia based on a sensory unit coated with at least one novel peptide |
| US11/681,094 US7579436B2 (en) | 2001-12-26 | 2007-03-01 | Peptide compound for measuring sulfur compound and ammonia |
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| TW090132419A TWI321570B (en) | 2001-12-26 | 2001-12-26 | Peptide compounds,and method of measuring sulfur compound and ammonia therewith |
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| TWI321570B (en) * | 2001-12-26 | 2010-03-11 | Ind Tech Res Inst | Peptide compounds,and method of measuring sulfur compound and ammonia therewith |
| NZ551202A (en) * | 2004-04-21 | 2009-08-28 | Nose Pty Ltd E | A detector for detecting molecules conveyed through a gaseous medium |
| AU2005236083B8 (en) * | 2004-04-21 | 2011-08-18 | E-Nose Pty Ltd | A detector for detecting molecules conveyed through a gaseous medium |
| KR20070083810A (ko) * | 2004-10-28 | 2007-08-24 | 가부시키가이샤 심스 | 질병 진단 시스템 |
| US7626474B2 (en) * | 2008-03-17 | 2009-12-01 | National Instruments Corporation | Compensated attenuator circuit and oscilloscope utilizing the same |
| US9850278B2 (en) | 2013-04-25 | 2017-12-26 | Carmel-Haifa University Economic Corp. | Synthetic anti-inflammatory peptides and use thereof |
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| US7060458B1 (en) * | 1997-08-14 | 2006-06-13 | Wyeth | Nucleic acid and amino acid sequences relating to Staphylococcus epidermidis for diagnostics and therapeutics |
| TW537879B (en) * | 2001-05-23 | 2003-06-21 | Ind Tech Res Inst | Diagnosing device by breath test including a multi-array of sensors |
| TWI321570B (en) * | 2001-12-26 | 2010-03-11 | Ind Tech Res Inst | Peptide compounds,and method of measuring sulfur compound and ammonia therewith |
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2001
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| Publication number | Publication date |
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| US20080114152A1 (en) | 2008-05-15 |
| US7579436B2 (en) | 2009-08-25 |
| US20030143750A1 (en) | 2003-07-31 |
| US7267989B2 (en) | 2007-09-11 |
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