疏水及羧甲基改質幾丁聚醣並其在抗菌和環保上之應用

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研究生：	武德勝 VO DUC THANG
論文名稱：	疏水及羧甲基改質幾丁聚醣並其在抗菌和環保上之應用 FUNCTIONALIZATION OF HYDROPHOBICALLY AND CARBOXYMETHYL MODIFIED CHITOSANS FOR ANTIMICROBIAL AND ENVIRONMENTAL APPLICATIONS
指導教授：	李振綱 Cheng-Kang Lee
口試委員:	何明樺 Ming-Hua Ho 蔡伸隆 Shen-Long Tsai 楊銘乾 Ming-Chien Yang 劉懷勝 Hwai-Shen Liu 董崇民 Trong-Ming Don
學位類別：	博士 Doctor
系所名稱：	工程學院 - 化學工程系 Department of Chemical Engineering
論文出版年：	2018
畢業學年度：	106
語文別：	英文
論文頁數：	104
中文關鍵詞：	幾丁聚醣、改性、疏水性幾丁聚醣、羧甲基幾丁聚醣、細胞捕獲、抗菌活性、甲基橙、薑黃素
外文關鍵詞：	Chitosan, modification, hydrophobically modified chitosan, carboxymethyl chitosan, cell capture, antibacterial activity, methyl orange, curcumin
相關次數：	點閱：332 下載：1
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幾丁聚醣是幾丁質經由脫乙醯處理所得的陽離子生物聚合物。其羥基和胺基可以被修飾以產生具有廣泛應用的羧甲基幾丁聚醣以及疏水性殼聚醣衍生物。羧甲基幾丁聚醣(carboxymethyl chitosan - CMCS)具有比幾丁聚醣本身更高的抗微生物活性，主要是由於其羥基和氨基之間的相互作用，導致氨基形成質子化的陽離子，有利於與一般帶負電荷之微生物細胞作用。銀離子可被在接枝於磁性納米顆粒上的CMCS原位還原成納米顆粒（AgNPs），作為磁性抗菌納米粒子（MNP @ CMCS-Ag）。由於CMCS和AgNPs的雙重作用，MNPs@CMCS-Ag可明顯提高其對浮游細菌細胞以及生物膜的抗菌活性。另一方面，經過十二烷醛與幾丁聚醣（CS）的胺基反應可合成出疏水性幾丁聚醣（HMCS），由於其C12烷基疏水鏈能與細胞作用，而表現出良好的止血功能。HMCS也可以通過其疏水尾端和細菌細胞外膜之間的相互作用而凝結細菌細胞。因此，HMCS塗層表面可被用來捕捉和固定化細菌細胞。HMCS的疏水尾端不僅可以與細菌細胞外膜產生相互作用，而且可以破壞細菌，導致細胞死亡。在與HMCS塗層接觸2小時後，超過50％的最初加入的大腸桿菌細胞（2.5 x10^4 CFU ）可被殺死。HMCS塗層不僅可成為耐用的抗菌表面，而且其高細胞捕獲能力可以來製造大腸桿菌的細胞陣列。此外，在劇烈的機械攪拌下，HMCS在弱酸性條件下溶解時可以產生非常穩定的泡沫。經過冷凍乾燥穩定形成的HMCS泡沫，可得耐用且質輕的泡棉（密度為32 mg mL-1）。除了幾丁聚醣的陽離子性質之外，接枝的C12烷基鏈也能幫助HMCS泡棉捕獲大腸桿菌細胞（約4.0x108個細胞mg-1海綿）。經過5次反覆的細胞移除操作，HMCS泡棉的大腸桿菌細胞去除能力，可以使用乙醇洗滌而再生回復 > 90％的細胞去除能力。此外，疏水烷基尾端的存在可降低HMCS的結晶度，並可增強與疏水化合物如甲基橙和膳食補充物薑黃素的相互作用。HMCS海綿體可增加MO的吸附（168 mg g-1），可作為環保性的生物吸收劑。而且，HMCS海綿體也表現出對薑黃素有效的吸附能力（39mg g-1），吸附有薑黃素的HMCS海綿體，預期具有增強的抗微生物和傷口癒合能力。

Chitosan, a well-known cationic biopolymer, is obtained from chitin after thorough deacetylation. The hydroxyl and amino groups can be modified to produce carboxymethyl chitosan and hydrophobically modified chitosan derivatives which have a wide range of applications. Carboxymethyl chitosan (CMCS) was known to have a much better antimicrobial activity than chitosan itself due to the interactions between the carboxyl and amino groups that leads to the formation of protonated cationic amino groups. Silver ions were in situ reduced to nanoparticles (AgNPs) on CMCS grafted magnetic nanoparticles as magnetic antimicrobial nanoparticles (MNPs@CMCS-Ag). MNPs@CMCS-Ag could significantly increase its antimicrobial activity against planktonic bacterial cells as well as existing biofilm due to the dual action of CMCS and AgNPs. On the other hand, hydrophobically modified chitosan (HMCS), synthesized by reacting dodecyl aldehyde with the amino groups of chitosan (CS) has demonstrated its good hemostatic property due to the hydrophobic tails. HMCS can also coagulate bacterial cells via the interactions between its hydrophobic tails and outer membrane of bacterial cells. Therefore, HMCS coated surface was employed to capture and immobilize bacterial cells. The hydrophobic tails of HMCS was found not only can interact with outer membrane of bacterial cells but also can disrupt it that leads to the death of cells. More than 50% of the initially loaded E. coli cells (2.5 x 10^4 CFU) could be killed after 2 h contact with HMCS coating. The facile HMCS coating not only generated a durable antimicrobial surface but was also employed to fabricate patterned E. coli cells arrays by taking advantage of its strong cells capture capacity. In addition, the HMCS can generate very stable foam when dissolved in mild acidic condition under vigorous mechanical stirring. A durable and lightweight (density of 32 mg mL-1) sponge was easily obtained by freeze-drying the stably formed HMCS foam. In addition to the cationic nature of chitosan, the grafted C12 alkyl chains were also able to help HMCS sponge for capturing E. coli cells (~4.0 x 10^8 cells mg-1 sponge). After 5 repeated cells removal operation, the removal capacity of HMCS sponge could be regenerated back to >90% by thorough washing with ethanol. Moreover, the presence of hydrophobic alkyl tails that lowers the crystallinity of HMCS and leads to an enhanced interaction with hydrophobic model compounds such as methyl orange and dietary supplement curcumin. The HMCS sponge demonstrated a significantly increased MO adsorption (168 mg g-1) that may find its place as an effective and sustainable bio-absorbents in environmental protections. Besides, HMCS sponge also demonstrated an effective adsorption capacity (39 mg g-1) toward the curcumin. The curcumin loaded HMCS sponge is expected to have enhanced antimicrobial and wound healing activity.

摘要    i
ABSTRACT    ii
ACKNOWLEDGEMENT    iv
ABBREVIATIONS    viii
LIST OF FIGURES    ix
LIST OF SCHEMES    xvi
LIST OF TABLES    xvii
CHAPTER 1    1
INTRODUCTION    1
1.    Background    1
2.    Objectives    2
CHAPTER 2    6
LITERATURE REVIEW    6
1.    Chitosan (CS)    6
2.    Antibacterial material    6
3.    Carboxymethyl chitosan (CMCS)    7
4.    Hydrophobically modified chitosan (HMCS)    8
5.    Dye adsorption    10
6.    Wound healing property of curcumin    10
CHAPTER 3    12
MATERIALS AND METHOD    12
1.    Materials    12
1.1.    Bacteria    12
1.2.    Chemical    12
2.    Bacterial culture medium    13
3.    Reagent    13
4.    Apparatus    14
5.    Characterization    15
CHAPTER 4    19
SILVER DEPOSITED CARBOXYMETHYL CHITOSAN-GRAFTED MAGNETIC NANOPARTICLES AS DUAL ACTION DELIVERABLE ANTIMICROBIAL MATERIALS    19
1.    PREPARATION AND CHARACTERIZATION    19
1.1.    Carboxymethyl chitosan (CMCS) preparation    19
1.2.    CS/CMCS grafted magnetic nanoparticles (MNPs@CS, MNPs@CMCS)    19
1.3.    In situ deposition of silver on MNPs and MNPs@CMCS (MNPs@Ag and MNPs@CMCS-Ag)    20
1.4.    Antibacterial effect    21
1.5.    Minimum inhibitory concentration (MIC)    21
1.6.    Biofilm disruption    22
2.    RESULTS AND DISCUSSION    22
2.1.    Characterization of CMCS and CMCS grafted MNPs (MNPs@CMCS)    22
2.2.    Silver deposited MNPs@CMCS (MNPs@CMCS-Ag)    26
2.3.    Antibacterial and biofilm removal effect    31
3.    CONCLUSION    36
CHAPTER 5    38
CELLS CAPTURE AND ANTIMICROBIAL EFECT OF HYDROPHOBICALLY MODIFIED CHITOSAN COATING ON ESCHERICHIA COLI    38
1.    PREPARATION AND CHARACTERIZATION    38
1.1.    Hydrophobically modified chitosan (HMCS) synthesis    38
1.2.    Cell suspension gelation induced by HMCS    38
1.3.    Surface coated with HMCS    38
1.4.    Antimicrobial activity of HMCS surface against E. coli    39
1.5.    Cells capture and patterning    39
2.    RESULTS AND DISCUSSION    40
2.1.    Characterization of HMCS    40
2.2.    HMCS induced cells gelation    43
2.3.    HMCS surface coating    46
2.4.    Antimicrobial effect of HMCS coating    51
2.5.    Cells capture on patterned HMCS surface    56
3.    CONCLUSION    58
CHAPTER 6    60
PREPARATION, CHARACTERIZATION AND APPLICATIONS OF HYDROPHOBICALLY MODIFIED CHITOSAN SPONGE    60
1.    HMCS SPONGE PREPARATION AND CHARACTERIZATION    60
1.1.    Experimental section    60
1.2.    Results and discussion    60
2.    ANTIMICROBIAL SPONGE PREPARED BY HYDROPHOBICALLY MODIFIED CHITOSAN FOR BACTERIAL REMOVAL    63
2.1.    Experimental section    63
2.1.1.    Bacteria removal ability of sponges    63
2.1.2.    Contact-killing activity of sponges    64
2.1.3.    Reusability of sponge for bacterial removal    64
2.2.    Results and discussion    64
2.2.1.    Bacteria removal ability of sponges    64
2.2.2.    Antibacterial effect of sponges    67
2.2.3.    Reusability of HMCS for cells removal    70
2.3.    Conclusion    71
3.    HYDROPHOBICALLY MODIFIED CHITOSAN SPONGE PREPARATION AND ITS APPLICATION FOR ANIONIC DYE REMOVAL    72
3.1.    Experimental section    72
3.1.1.    Adsorption equilibrium    72
3.1.2.    Adsorption kinetic    73
3.1.3.    Reusability of CS and HMCS sponge for MO adsorption    73
3.2.    Results and discusion    73
3.2.1.    Effect of ionic strength and pH on adsorption    74
3.2.2.    Adsorption kinetic    75
3.2.3.    Adsorption isotherm    77
3.2.4.    Adsorption thermodynamic    80
3.2.5.    Reused ability of CS and HMCS sponge    81
3.3.    Conclusion    83
4.    HYDROPHOBICALLY MODIFIED CHITOSAN SPONGE ADSORBED CURCUMIN AS POTENTIAL MATERIAL FOR WOUND DRESSING    84
4.1.    Experimental section    84
4.1.1.    Curcumin adsorption    84
4.1.2.    DPPH* free radical scavenging activity    84
4.1.3.    Evaluation of whole-blood clotting    85
4.2.    Results and discussion    85
4.2.1.    Curcumin adsorption    85
4.2.2.    DPPH* free radical scavenging activity    87
4.2.3.    Evaluation of whole-blood clotting    88
4.3.    Conclusion    88
CHAPTER 7    89
FUTURE WORK AND SUGGESTION    89
REFERENCES    94

                                

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