臺灣博碩士論文加值系統

In this thesis, we describe about drug delivery system and the uses of azobenzene amphiphilic moieties as a potential molecules toward liposome-based drug delivery. How to synthesize azobenzene amphiphilic structure is the point of this thesis and this article provides a reaction pathway to synthesize amphiphilic structure. In this article, we also test the photoswitch properties of the amphiphilic structure to determine the effectiveness of visible light radiation for azobenzene isomerization.

Table of Content

Abrreviation table......................................................................................... i
Abstract..................................................................................................... iii
Table of Content.......................................................................................... iv
Table List................................................................................................. vi
Figure List................................................................................................. vii
Scheme List............................................................................................... viii
Chapter 1. Introduction................................................................................. 1
1. Drug Delivery System (DDS) ............................................................. 1
2. Light Sensitive Liposome..................................................................... 3
1. Photoisomerization………………................................................... 5
2. Photocleavage…...………….……................................................... 6
3. Photocrosslinking/Photopolymerization ……………………......... 7
3. Click Chemistry and its Application in Drug Delivery System........... 8
4. Azobenzene and Its Preparation......................................................... 11
1. Azo coupling reaction..................................................................... 12
2. Mills Reaction................................................................................ 14
3. Wallach Reaction............................................................................ 16
5. Azobenzene Photoswitch and Application......................................... 17
6. Research Motivation…………………………………………………26
Chapter 2. Results and Discussion ............................................................. 28
1. Retrosynthetic Analysis of Triazole................................................... 28
2. Alkyne building block synthetic......................................................... 29
3. Azide building block synthesis........................................................... 31
4. Click reaction and deprotection reaction.............................................. 33
Chapter 3. Conclusion................................................................................ 42
Chapter 4. Experimental Section................................................................ 43
1. General Information........................................................................... 43
2. Experimental Procedure and Physical Data....................................... 44
References.................................................................................................. 51
Appendix.................................................................................................... 54

References

1.Golan, D. E.; Armstrong, E. J.; Armstrong, A. W. Principles of pharmacology: The Pathophysiological Basis of Drug Therapy, 4th ed.; Lippincott Williams&Wilkins: Philadelphia, 2008.
2.Jain, K. K. Drug delivery systems—an overview. Humana: New York, 2008.
3.Bajpai, A. K.; Shukla, S. K.; Bhanu, S. Prog Polym Sci. 2008, 33, 1088-1118.
4.Robinson, J. R.; Lee, V. H. L. Controlled Drug Delivery: Fundamentals and Applications. Dekker: New York, 1987.
5.Bangham, A. D.; Standish, M. M.; Watkins, J. C. J. Mol. Biol. 1965, 13, 238-252.
6.Paasonen, L.; Romberg, B.; Storm, G. Bioconjug Chem. 2007, 18, 2131-2136.
7.Sharma, A.; Sharma, U. S. Int J Pharm. 1997, 154, 123-140.
8.L., Paasonen; B., Romberg; G., Storm; M., Yliperttula; A., Urtti; W. E., Hennick. Bioconjug Chem. 2007, 18, 2131-2136.
9.Betz, G.; Aeppli, A.; Menshutina, N.; Leuenberger, H. Int. J. Pharm. 2005, 296, 44−54.
10.Mu, L.; Sprando, R. L. Pharm. Res. 2010, 27, 1746-1749.
11.Taylor, T. M.; Davidson, P. M.; Bruce, B. D.; Weiss, J. Crit. Rev. Food Sci. Nutr. 2005, 45, 587−605.
12.Mozafari, M. R.; Johnson, C.; Hatziantoniou, S.; Demetzos, C. J. Liposome Res. 2008, 18, 309-327.
13.Mozafari, M. R. Cell Mol Biol Lett. 2005, 10, 711-719.
14.Miranda, D.; Lovell, J. F. Bioeng Transl Med. 2016, 1, 267-276.
15.Leung, S. J.; Romanowski, M. Theranostics. 2012, 2, 1020-1036.
16.Hester, T. J.; Dennison, S. R.; Baker, M. J.; Snape, T. J. Org Biomol Chem. 2015, 13, 8067–8070.
17.Merino, E.; Ribagorda, M. Beilstein J Org Chem. 2012, 8, 1071–1090.
18.Pelliccioli, A. P.; Wirz, J. Photochem Photobiol Sci. 2002, 1, 441–458.
19.Bayer, A. M.; Alam, S.; Mattern-Schain, S. I.; Best, M. D. Chem Eur J. 2014, 20, 3350–3357.
20.Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004–2021.
21.Bock, V. D.; Hiemstra, H.; Maarseveen, J. H-V. Eur. J. Org. Chem. 2006, 1, 51–68.
22.Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210–216.
23.Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed., Engl. 2002, 41, 2596–2599.
24.Worell, B. T.; Malik, J. A.; Fokin, V. V. Science. 2013, 340, 457-460.
25.Immordino, M. L.; Dosio, F.; Cattel, L. Int. J. Nanomed. 2006, 1, 297–315.
26.Merino, Estı´baliz. Chem. Soc. Rev. 2011, 40, 3835–3853.
27.Zhen, W.; Han, H.; Anguiano, M.; Lemere, C.; Cho, C. G.; Lansbury, P. T. J. Med. Chem. 1999, 42, 2805-2815.
28.Haghbeen, K.; Tan, E. W. J. Org. Chem., 1998, 63, 4503-4505.
29.Svele, I.; Zollinger, H. Top. Curr. Chem. 1983, 112, 1-66.
30.Davey, H. H.; Lee, R. D.; Marks, T. J. J. Org. Chem. 1999, 64, 4976-4979.
31.Ueno, K.; Akiyoshi, S. J. Am. Chem. Soc. 1954, 76, 3670-3672.
32.Shimao, I.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 643-644.
33.Shimao, I.; Matsumura, S. Bull. Chem. Soc. Jpn. 1976, 49, 2294-2297.
34.Hartley, G. S. Nature. 1937, 140, 281-281.
35.Dong, M.; Babalhavaeji, A.; Samanta, S.; Beharry, A. A.; Woolley, G. A. Acc. Chem. Res. 2015, 48, 2662-2670.
36.Lesch, J. E. The first miracle drugs: How the sulfa drugs transformed medicine; Oxford University Press: New York, 2007.
37.Thomas, B. H.; Whitehouse, L. W.; Solomonraj, G.; Paul, C. J. J. Pharm. Sci. 1990, 79, 321-325.
38.Brown, M. A.; Devito, S. C. Crit. Rev. Environ. Sci. Technol. 1993, 23, 249-324.
39.Cheong, W. F.; Prahl, S. A.; Welch, A. J. IEEE J. Quantum Electron.
1990, 26, 2166-2185.
40.Beharry, A. A.; Sadovski, O.; Woolley, G. A. J. Am. Chem. Soc. 2011, 133, 19684-19687.
41.Pang, Juan; Tian, Ziqi; Ma, Jing. Chemical Physics Letters. 2014, 613, 110-114.
42.Samanta, S.; Beharry, A. A.; Sadovski, O.; McCormick, T. M.; Babalhavaeji, A.; Tropepe V.; Woolley, G. A. J. Am. Chem. Soc. 2013, 135, 9777-9784.
43.Dong, M.; Babalhavaeji, A.; Collins, C. V.; Jarrah, K.; Sadovski, O.; Dai Qiuyun; Woolley, G. A. J. Am. Chem. Soc. 2017, 139, 13483-13486.
44.Liu, Danyang; Wang, Sijia; Xu, Shouhong; Liu, Honglai. Langmuir. 2017, 33, 1004–1012.
45.Montalbetti, C. A. G. N.; Falque, V. Tetrahedron. 2005, 61, 10827-10852.