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研究生：	謝怡宣 Hsieh, Yi-Hsuan
論文名稱：	殼層以及核層交聯聚電解質複合粒子應用於藥物載體 Shell- and core- cross-linked polyelectrolyte complex particles as drug carriers
指導教授：	詹正雄 JAN, JENG-SHIUNG
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2013
畢業學年度：	101
語文別：	中文
論文頁數：	100
中文關鍵詞：	聚電解質、礦化複合粒子、交聯
外文關鍵詞：	polyelectrolyte, complex particles, silica, hybrid particles, cross-link
相關次數：	點閱：109 下載：1
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帶正電聚電解質與帶負電聚電解質因靜電作用力互相吸引，形成多種不同型態之複合產物，如：複合粒子、膜層、膠體，及不規則析出… …等，而複合產物之物性與化性大多與組成聚電解質有關，透過巧妙的設計，就能使複合產物保有原組成聚電解質之酸鹼應答或特殊構形等功能。
本研究中，帶正電之聚賴胺酸(PLL)與帶負電之聚丙烯酸(PAA)透過靜電作用，於水溶液中自組裝形成奈米複合粒子，藉由控制鹽類濃度、PLL和PAA鏈長、PLL與PAA相對比例… …等參數，以改變所形成奈米粒子之粒徑大小與界面電位，並經由二氧化矽礦化作用、殼層交聯反應以達到穩固複合粒子的目的；首先，吾人利用仿生合成，以複合奈米粒子為模板沉析二氧化矽，形成有機/無機核心交聯粒子，此礦化粒子會因聚電解質官能基的不同而顯示出不同的等電點；本研究亦藉由交聯劑與複合粒子表面之過量聚電解質反應，生成殼層交聯粒子。
以電解質複合粒子所製備出之核心/殼層交聯複合粒子，能在稀釋條件及不同酸鹼值下保持穩定，在酸鹼應答型藥物載體的應用上極具潛力，亦在觸媒、仿生性包覆體，及功能性奈米反應器… … 等生物材料上，有極高的應用價值。

Complexes of two oppositely charged polyelectrolytes could lead to a variety of outcomes, for instance: precipitation, membranes, gels, and particles. The resulting complexes exhibited the structure and property of the constituent polyelectrolytes such as thermal or pH responsiveness and ordered conformation.
In this study, polyelectrolyte complex (PEC) particles were obtained by electrostatic interactions between positively charged poly(L-lysine) (PLL) and negatively charged poly(acrylic acid) (PAA) in aqueous medium. The influence of chain length, weight ratio of PLL and PAA, and solution condition on the formation of the PEC particles was studied and characterized by DLS, Zeta potential, and TEM. Silica mineralization and shell cross-linking were applied to stabilize the PEC particles in extreme solution conditions or dilution.
PEC-silica hybrid particles could be prepared by mineralizing silica in the complex cores, resulting in core-cross-linked particles. The hybrid particles exhibited different iso-electric points that depended on the constituent polyelectrolyte. The shell cross-linked micelles (SCMs) could be prepared by cross-linking the excess polyelectrolyte on the corona. The shell- and core-cross-linked PEC particles were stable at different pH values. The feasibility of using the cross-linked PEC particles as pH-sensitive drug carriers was evaluated in this study. With the unique feature of the biocompatible PEC-silica hybrid particles and SCMs, they could be developed as drug carriers, biomimetic encapsulants, functional nanobioreactiotors, and so forth.

目錄
摘要	I
Abstract	II
誌謝	III
第一章	緒論	1
第二章	文獻回顧	3
2.1	聚胺基酸之特性與應用價值	3
2.2	聚電解質複合材料	5
2.2.1	聚電解質複合物	5
2.2.2	聚電解質複合產物之型態分類與應用	6
2.2.3	聚電解質複合微胞之生物訊號(離子強度、酸鹼、還原電位、溫度)應答	6
2.3	生物礦物質合成及二氧化矽礦化作用	11
2.3.1	仿生合成之優勢	11
2.3.2	自然界常見之生物礦物質(碳酸鈣、磷酸鈣、二氧化矽、無機氧化物)	12
2.3.3	以人工合成之多肽為模板合成二氧化矽	14
2.4	交聯	16
2.4.1	微胞粒子之交聯	16
2.4.2	Genipin優點與交聯機制	21
第三章	實驗方法與儀器設備	24
3.1	實驗藥品	24
3.2	聚胺酸和聚丙烯酸(PAA)之合成	26
3.2.1	純化丙烯酸第三丁酯(tBA)單體	26
3.2.2	純化ATRP觸媒(CuBr)	26
3.2.3	利用ATRP聚合丙烯酸第三丁酯	26
3.2.4	去除聚丙烯酸第三丁酯保護基	27
3.2.5	利用NCA開環聚合合成PLL	27
將單體	28
3.2.6	聚胺基酸之保護基(R-group)去除	29
3.3	製備聚電解質複合粒子	29
3.4	製備交聯複合粒子	30
3.4.1	以Genipin交聯帶正電複合粒子	30
3.4.2	以Cystamine交聯帶負電複合粒子	30
3.5	礦化複合粒子之製備與應用	30
3.5.1	複合粒子之礦化反應與其酸鹼應答	30
3.5.2	礦化複合粒子之藥物釋放	31
3.6	複合粒子之藥物包覆實驗	31
3.7	特性分析與性質測試	31
3.7.1	核磁共振光譜儀	31
3.7.2	凝膠滲透層析儀	32
3.7.3	動態光散射粒徑分析儀	33
3.7.4	Zeta potential	34
3.7.5	穿透式電子顯微鏡	35
3.7.6	紅外線光譜儀	36
3.7.7	圓二色光譜儀	37
3.7.8	熱重分析儀	39
第四章	結果與討論	40
4.1	聚電解質之合成與分析	40
4.1.1	聚丙烯酸與聚賴胺酸之合成	40
4.1.2	聚丙烯酸與聚賴胺酸之分析	40
4.2	PLL/PAA複合粒子	42
4.2.1	組成重量百分比對PLL/PAA複合粒子帶電之影響	43
4.2.2	在純水中製備之PLL/PAA複合粒子之粒徑	44
4.2.3	鹽類對PLL/PAA複合粒子之影響	50
4.2.4	PLL/PAA複合粒子之構形和二級結構	53
4.3	聚電解質複合粒子之礦化作用	55
4.3.1	製備礦化複合粒子	55
4.3.2	礦化反應對複合粒子之粒徑影響	59
4.3.3	礦化複合粒子帶電之酸鹼應答	62
4.3.4	礦化複合粒子之構形與二級結構	65
4.3.5	礦化粒子之分析及有機/無機組成重量百分比	68
4.4	聚電解質複合粒子之交聯作用	69
4.4.1	製備交聯複合粒子	70
4.4.2	交聯複合粒子之粒徑與粒徑分布	71
4.4.3	交聯複合粒子之酸鹼應答	74
4.4.4	交聯粒子之分析	78
4.5	聚電解質複合粒子作為藥物載體之應用	83
4.5.1	複合粒子包覆率及粒徑變化	84
4.5.2	包藥複合粒子之交聯	86
第五章	結論	88
第六章	參考文獻	90

 
表目錄
Table.2- 1 雙功能反應劑與對應反應官能基76	17
Table.4- 1 聚電解質分子量與PDI分析	41
Table.4- 2複合粒子之礦化條件	58
Table.4- 3 複合粒子礦化反應之結果	60
Table.4- 4 在不同粒子濃度下的交聯結果	71
Table.4- 5 PLL50/PAA50_30%之藥物包覆結果	85
Table.4- 6 交聯複合粒子前後DLS分析	86
 
圖目錄
Fig.2- 1多肽之二級結構:a)random coil, b)α-helix, c)β-sheet3	3
Fig.2- 2 PLL二級結構在不同環境下之改變7	4
Fig.2- 3 多肽載體型態8	5
Fig.2- 4酸鹼應答造成複合粒子內體瓦解現象23	8
Fig.2- 5 (A) 具pH應答之化學鍵 (B) pH造成聚電解質帶電性轉變24	8
Fig.2- 6雙硫交聯劑在細胞中解交聯現象31	9
Fig.2- 7 (PiPrOx-b-PAA)在溫度高於Tc下之聚集效應36	10
Fig.2- 8 (A) 老鼠門牙之砝瑯柱狀結構、(B) 珍珠層中片狀混和結構37	12
Fig.2- 9 矽藻之礦化細胞壁結構45	13
Fig.2- 10 magnetotactic bacteria中磁性奈米粒子52	14
Fig.2- 11透過模板機制與相變化之二氧化矽形成示意圖53	15
Fig.2- 12官能基化學交聯反應76	17
Fig.2- 13 雙鍵官能基之光啟動交聯反應；黑點表示光起始劑76	19
Fig.2- 14 cinnamate、coumarin、thymine之光啟動環加成反應76	20
Fig.2- 15 矽氧烷縮合反應94	21
Fig.2- 16 4-(1-methylsilacyclobutyl) styrene共聚物結構94	21
Fig.2- 17 Genipin反應機制	23
Fig.3- 1 PAA合成步驟	27
Fig.3- 2 NCA製備流程	28
Fig.3- 3 Poly(z-L-lysine)合成圖	29
Fig.3- 4利用GPC 測量分子量	33
Fig.3- 8以圓二色光譜儀測定二級結構之圖形	38

Fig.4- 1 PtBA之NMR圖譜(in MeOD )	41
Fig.4- 2 PtBA之GPC分析	42
Fig.4- 3 聚電解質複合粒子形成示意圖	43
Fig.4- 4 PLL/PAA複合粒子在純水下之Zeta Potential	44
Fig.4- 5純水中PAA50與不同鏈長PLL形成複合粒子粒徑	45
Fig.4- 6純水中PAA180與不同鏈長PLL形成複合粒子粒徑	46
Fig.4- 7 PLL50/PAA180在不同組成下DLS粒徑分布圖	46
Fig.4- 8 PLL100/PAA180在不同組成下DLS粒徑分布圖	47
Fig.4- 9 PLL250/PAA180在不同組成下DLS粒徑分布圖	48
Fig.4- 10純水中短鏈PAA50與不同鏈長之PLL形成複合粒子之粒徑分布	49
Fig.4- 11純水中長鏈PAA180與不同鏈長之PLL形成複合粒子之粒徑分布	49
Fig.4- 12 0.02N PBS Buffer中PAA180與不同鏈長之PLL形成複合粒子之粒徑	51
Fig.4- 13 0.02N PBS Buffer中短鏈PAA50與不同鏈長之PLL形成複合粒子之粒徑	51
Fig.4- 14 0.02N PBS Buffer中PAA180與不同鏈長之PLL形成複合粒子之粒徑分布	52
Fig.4- 15 0.02N PBS Buffer中PAA50與不同鏈長之PLL形成複合粒子之粒徑分布	52
Fig.4- 16 PLL50/PAA50_55%-0.02 N PBS	53
Fig.4- 17 PLL50/PAA50_55%-DI water	53
Fig.4- 18 PLL50/PAA50_70%-DI water	53
Fig.4- 19 PLL/PAA複合粒子二級結構分析	54
Fig.4- 20 PLL/PAA複合粒子之礦化作用	55
Fig.4- 21 PLL100/PAA50在0.02N PBS buffer中粒徑與帶電分析	57
Fig.4- 22 PLL100/PGA250於0.02N PBS buffer中粒徑與帶電分析	57
Fig.4- 23 PLL100/PSS2000於0.01N PBS buffer粒徑與帶電分析	57
Fig.4- 24 PLL100/PAA50礦化反應六小時之粒徑	60
Fig.4- 25 PLL100/PAA50礦化粒子粒徑分布圖	61
Fig.4- 26 PLL100/PSS2000礦化粒子粒徑分布圖	62
Fig.4- 27不同負電官能基礦化複合粒子之酸鹼應答	63
Fig.4- 28礦化複合粒子在不同重量百分比組成之酸鹼應答	64
Fig.4- 29礦化複合粒子在不同礦化時間下之酸鹼應答	64
Fig.4- 30交聯對礦化粒子酸鹼應答之影響	65
Fig.4- 31 PLL100/ PAA50_60%_礦化6小時之礦化粒子	66
Fig.4- 32 PLL100/ PAA50_60%_礦化1.5小時之礦化粒子	66
Fig.4- 33 PLL100/ PSS2000_40%_礦化3.5小時之礦化粒子	67
Fig.4- 34礦化粒子之IR分析	67
Fig.4- 35礦化粒子之二級結構	68
Fig.4- 36礦化粒子有機/無機組成百分比	69
Fig.4- 37以Genipin交聯帶正電複合粒子之PLL Shell	70
Fig.4- 38 以Cystamine交聯帶負電複合粒子之PAA Shell	70
Fig.4- 39 以Cystamine交聯PAA shell對負電複合粒子之粒徑影響	72
Fig.4- 40以Genipin交聯PLL shell對正電複合粒子之粒徑影響	73
Fig.4- 41 Cystamine交聯PAA Shell前後之粒徑分布圖	73
Fig.4- 42 Genipin交聯PLL Shell前後之粒徑分布圖	74
Fig.4- 43交聯帶負電粒子之帶電酸鹼應答	75
Fig.4- 44 負電交聯粒子粒徑酸鹼應答	76
Fig.4- 45交聯帶正電粒子之帶電酸鹼應答	76
Fig.4- 46正電交聯粒子粒徑酸鹼應答	77
Fig.4- 47正電交聯粒子酸鹼應答粒徑分布	77
Fig.4- 48交聯負電複合粒子之IR分析	79
Fig.4- 49交聯劑量對複合粒子帶電量的影響	79
Fig.4- 50以Genipin交聯PLL之UV特徵峰分析	80
Fig.4- 51 PLL50/PAA50_55%	81
Fig.4- 52 PLL50/PAA50_70%	81
Fig.4- 53 以Cystamine交聯PLL50/PAA50_55%之PAA Shell	81
Fig.4- 54以Genipin交聯PLL50/PAA50_70%之PLL Shell	81
Fig.4- 55 稀釋PLL/PAA複合粒子之粒徑分布圖	82
Fig.4- 56稀釋PLL/PAA交聯複合粒子粒徑分布圖	83
Fig.4- 57 包覆DOX之PLL50/PAA50_55%複合粒子	85
Fig.4- 58 包藥及交聯造成粒徑分布改變之DLS分析	87







                                    

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