利用分子結構快速估算藥物與染料分子於超臨界二氧化碳中之溶解度

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王暄文(Hsuan-Wen Wang) 查詢紙本館藏

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化學工程與材料工程學系

論文名稱

利用分子結構快速估算藥物與染料分子於超臨界二氧化碳中之溶解度

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至系統瀏覽論文 (2026-6-30以後開放)

摘要(中)

本研究應用PSRK狀態方程式和PR+COSMOSAC (PRCS)狀態方程式於預測藥物和染料分子在超臨界二氧化碳中的溶解度。基於官能基貢獻概念的PSRK狀態方程式中所需溶質之臨界性質可利用NRR官能基貢獻法或以量子化學計算為基礎的PRCS 狀態方程式來估算。在PRCS狀態方程式中，所探討溶質的分子結構是QM/COSMO溶合計算所需的唯一資訊，藉以產生相平衡計算所需的資訊。在計算溶解度的固體與超臨界流體相平衡計算中，溶質的固相逸壓可應用溶質的熔點溫度和熔化焓獲得，但大部分新合成之溶質尚缺乏所需的熔點性質，此外溶質的固相逸壓也可由溶質的氣固相平衡線為參考狀態求得。為了克服所需熔點性質實驗數據的缺乏，本研究中將首次系統化的探討利用修改參數後之Lee-Kesler (LK)方程式來估算昇華壓，並了解其應用於預測固體溶質於超臨界二氧化碳中溶解度的精確度。LK方程式中所需溶質之臨界性質亦同樣透過上述NRR或PRCS二方法估算求得，應用本方法進行溶解度預測僅需溶質之分子結構。
本研究共探討了99種藥物溶質和58種染料溶質。由於使用PRCS進行相平衡計算時，若是搭配迴歸昇華壓修改參數的LK方程式，則會產生溶解度的計算結果系統性高估的問題，因此改以搭配迴歸溶解度修改參數的LK方程式進行計算。由於官能基貢獻法會面臨缺乏相互作用參數和官能基定義的問題，PSRK僅能預測其中57種藥物溶質的溶解度，PSRK搭配使用NRR與PRCS估算之臨界性質進行溶解度預測所得到之平均對數誤差(ALD-x)分別為0.914和0.842，對於相同的57種溶質，PRCS搭配使用NRR與PRCS估算之臨界性質行溶解度預測所得到的ALD-x分別為1.597和0.893。PR+COSMOSAC的計算僅需分子結構，不存在缺乏參數的問題，因此可用於預測所有已知分子結構之固體溶質，在99種藥物溶質的溶解度預測中獲得之ALD-x為0.871，而在58種染料溶質的溶解度預測中獲得之ALD-x為1.138。

摘要(英)

The PSRK EOS and PR+COSMOSAC (PRCS) EOS were used to predict the solubility of drug-like and dye-like molecules in supercritical carbon dioxide (SCCO2). The required input of critical properties of the studied solute for group-contribution model PSRK were obtained by either NRR model (based on the group contribution concept) or PRCS EOS (based on the first-principles solvation model). In PRCS EOS, the molecular structure of the studied solute was the only input for QM/COSMO solvation calculation to generate the key information for phase equilibrium calculations. In the solid-fluid equilibrium calculation, the solid phase fugacity of the solute can be obtained from its melting point and heat of fusion, but most of the newly synthesized solutes are lack of experimental melting properties. Besides, the solid phase fugacity can also be determined with the solid-vapor equilibrium line as the reference state. In order to overcome the lack of required experimental melting properties, the accuracy of using sublimation pressure estimated from the Lee-Kesler (LK) equation in predicting solid solute solubility was investigated. The required critical properties for the LK equation were estimated by the aforementioned NRR or PRCS methods. Thus, the proposed approach requires the only input of molecular structure of the studied solute.
A total of 99 drug-like and 58 dye-like solutes were investigated in this study. When using PRCS for phase equilibrium calculation, if it is combined with the LK equation of regression sublimation pressure to optimize the parameters, the predicted result of solubility will be systematically overestimated, so the calculation is changed to the LK equation with regression solubility to optimize the parameters. Because the group contribution method faces the issue of lacking interaction parameters and functional group definitions, PSRK can only predict the solubility of 57 drug-like solutes, the average logarithmic deviation in solubility (ALD-x) of PSRK using critical properties from NRR and PRCS are 0.914 and 0.842, respectively. The ALD-x of PRCS using critical properties from NRR and PRCS are 1.597 and 0.911, respectively, for the same 57 solutes. PR+COSMOSAC requires the molecular structure as the only input, and thus can be applied to describe all solid solutes. The ALD-x for predicting solubility of 99 drug-like and 58 dye-like solutes is 0.974 and 1.138, respectively.

關鍵字(中)

★ 超臨界二氧化碳
★ 溶解度

關鍵字(英)

論文目次

中文摘要 i
Abstract ii
目錄 iii
圖目錄 v
表目錄 vii
第一章緒論 1
1-1 超臨界流體性質簡介 1
1-2 回顧固體溶質溶解度之計算方法 4
1-3 研究動機 8
第二章計算原理與細節 9
2-1 溶解度計算細節 9
2-2 PSRK EOS 13
2-2-1 官能基貢獻法估算臨界性質 14
2-2-2 PR+COSMOSAC EOS計算臨界性質 16
2-2-3 偏心因子的計算方法 17
2-3 PR+COSMOSAC EOS 18
2-3-1 溶合自由能(Solvation Free Energy) 20
2-3-2 QM/COSMO資訊細節 25
第三章藥物溶質結果 26
3-1 使用熔點性質或昇華壓對溶解度計算的影響 27
3-2 使用Lee-Kesler或Ambrose-Walton方法對昇華壓計算的影響 29
3-3 不同方法獲得的昇華壓對溶解度計算的影響 32
3-4 分子結構複雜度效應 42
3-5 使用溶解度數據進行LK方程式參數優化 45
3-6 探討PR+COSMOSAC環狀修正係數對溶解度計算的影響 49
第四章染料溶質結果 53
4-1 使用熔點性質或昇華壓對溶解度計算的影響 53
4-2 使用溶解度數據進行LK方程式參數優化 55
4-3 探討PR+COSMOSAC環狀修正係數對溶解度計算的影響 57
第五章結論 59
參考文獻 60
附錄(一) 藥物溶質的性質資訊和溶解度實驗數據 73
附錄(二) 染料溶質的性質資訊和溶解度實驗數據 76
附錄(三) 臨界性質計算結果 78
附錄(四) 含有昇華壓實驗數據的分子 84
附錄(五) 額外挑選含有昇華壓實驗數據的分子 85
附錄(六) 官能基切割示意圖 86
附錄(七) 藥物溶質的分子結構 87
附錄(八) 染料溶質的分子結構 96
附錄(九) LK和AW方程式中的參數 101

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指導教授

謝介銘

審核日期

2021-7-21

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