Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery
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Q.-R. Yang
Abstract
Design and synthesis of a new galactolipid 6 with carbamate was described in this work. Compounds 1–3 were obtained easily with classical synthesis methods which were improved a little. The influence of the solvent and different groups of the tertiary amine 4 for the quaternization reaction was discussed. The mixture of chloroform, ammonia and methanol was used well as the elution for separating compound 5 with silica gel column chromatograph. The CMC and γCMC was 2.40 · 10−4 mol/L and 26.1 mN m−1, respectively by surface tension measurement. Vesicles can be formed according to the theory of critical packing parameter since the value of the critical packing parameter was 0.83 at CMC, and it was confirmed by TEM micrograph.
Kurzfassung
In dieser Arbeit wurde die Herstellung eines neuen Galactolipids 6 mit Carbamat beschrieben. Die Verbindungen 1–3 wurden einfach mittels klassischer, geringfügig verbesserter Synthesemethoden erhalten. Der Einfluss des Lösemittels und der verschiedenen Gruppen des tertiären Amins 4 in der Quaternisierungsreaktion wurde diskutiert. Die Mischung aus Chloroform, Ammoniak und Methanol war ein gutes Elutionsmittel für die chromatographische Trennung der Verbindung 5 in der Silicagel-Säule. Die kritische Mizellbildungskonzentration CMC beträgt 2,40 · 10−4 mol/L und die Oberflächenspannung 26,1 mN m−1. Vesikel wurden entsprechend der Theorie der kritischen Packungsparameter gebildet. Der Wert des kritischen Packungsparameters bei der CMC ist 0,83. Dies konnte mit TEM-Mikroskopie bestätigt werden.
References
1. Hyde, S. C., Gill, D. R., Higgins, C. F., Trezise, A. E., MacVinish, L. J., Cuth-bert, A. W., Ratcliff, R., Evans, M. J. and Colledge, W. H.: Nature362 (1993) 250–255. 10.1038/362250a0Suche in Google Scholar
2. Parker, S. E., Vahlsing, H. L., Serfilippi, L. M., Franklin, C. L., Doh, S. G., Gromkowski, S. H., Lew, D., Manthorpe, M. and Norman, J.: Hum. Gene. Ther.6 (1995) 575–590. 10.1089/hum.1995.6.5-575Suche in Google Scholar
3. Timiryasova, T. M., Chen, B. and Fodor, I.: Gene Med.3 (2001) 468–477. 10.1002/jgm.205Suche in Google Scholar
4. Ashwell, G. and Harford, J.: Annu. Rev. Biochem.51 (1982) 531–554. 10.1146/annurev.bi.51.070182.002531Suche in Google Scholar
5. Hashida, M., Nishikawa, M., Yamashita, F. and Takakura, Y.: Adv. Drug Deliv. Rev.52 (2001) 187–196. 10.1016/S0169-409X(01)00209-5Suche in Google Scholar
6. Yuzawa, H., Fujioka, H., Mizoe, A., Azuma, T., Furui, J., Nishikawa, M., Hashi-da, M. and Kanematsu, T.: Hepato-Gastroenterology52 (2005) 839–843.Suche in Google Scholar
7. Sun, X., Li, H., Wu, Y., Hu, H. Y. and Zhang, Z. R.: J. Drug Target.13 (2005) 121–128. 10.1080/10611860400024714Suche in Google Scholar
8. Mahidhar, Y. V., Mukthavaram, R. and Chaudhuri, A.: J. Med. Chem.47 (2004), 3938–3948. 10.1021/jm030464iSuche in Google Scholar
9. Mukthavaram, R., Marepally, S. and Mahidhar, Y. V.: Biomaterials30 (2009) 2369–2384. 10.1016/j.biomaterials.2008.12.074Suche in Google Scholar
10. Zhang, S. M., Qiao, W. H., Chen, Y. X. and Liu, D. L.: Tenside Surf. Det.46 (2009) 228–231.10.3139/113.110028Suche in Google Scholar
11. Bangham, A. D., Standish, M. M. and Watkins, J. C.: J. Mol. Biol.13 (1965) 238–253. 10.1016/S0022-2836(65)80093-6Suche in Google Scholar
12. Feitosa, E. and Brown, W.: Langmuir13 (1997) 4810–4816. 10.1021/la962034jSuche in Google Scholar
13. Harris, J. R., Roos, C., Djalali, R., Rheingans, O., Maskos, M. and Schmidt, M.: Micron30 (1999) 289–298. 10.1016/S0968-4328(99)00034-7Suche in Google Scholar
14. Bukowski, R., Morris, L. M., Woods, R. J. and Weimar, T.: Eur. J. Org. Chem.14 (2001) 2697–2705. 10.1002/1099-0690(200107)2001:14<2697::AID-EJOC2697>3.0.CO;2-0Suche in Google Scholar
15. Zhao, H., Liu, J., Lu, L. L. and Xiao, M.: Fine Chemicals25 (2008) 660–663.Suche in Google Scholar
16. Kieburg, C., Sadalapure, K. and Lindhorst, T. K.: Eur. J. Org. Chem.11 (2000) 2035–2040. 10.1002/1099-0690(200006)2000:11<2035::AID-EJOC2035>3.0.CO;2-VSuche in Google Scholar
17. Maier, Martin A., Yannopoulos, C. G., Mohamed, N., Roland, A., Fritz, H., Mohan, V., Just, G. and Manoharan, M.: Bioconjugate Chem.14 (2003) 18–29. 10.1021/bc020028vSuche in Google Scholar
18. Coles, Harold W., Dodds, M. L. and Bergeim, F. H.: J. Am. Chem. Soc.60 (1938) 1020–1022. 10.1021/ja01272a011Suche in Google Scholar
19. Quagliotto, P., Viscardi, G., Barolo, C., D'Angelo, D., Barni, E., Compari, C., Duce, E. and Fisicaro, E.: J. Org. Chem.70 (2005) 9857–9866. 10.1021/jo051579sSuche in Google Scholar
20. Zemplen, G.: J. G. Chem. Ber.60 (1927) 1555–1564.10.1002/cber.19270600717Suche in Google Scholar
21. Gu, T. R., Zhu, B. Y. and Li, W. L.: Surface Chemistry, Science Press, China, 2001.Suche in Google Scholar
22. Tanford, C.: Wiley-Interscience, New York, 1973.Suche in Google Scholar
23. Israelachvili, J. N.: Intermolecular and surface forces: with applications to colloidal and biological systems, Academic Press, London, 1985.Suche in Google Scholar
© 2010, Carl Hanser Publisher, Munich
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Environmental/Technical Chemistry
- Alkyl Polyglycoside-Sorbitan Ester Formulations for Improved Oil Recovery
- Novel Surfactants
- Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants
- Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery
- Physical Chemistry
- Dynamics of Formation of Vesicles Studied by Highly Time-resolved Stopped-flow Experiments
- Ion Extractant as Cosurfactant at the Water-Oil Interface in Microemulsions
- Microemulsions with Mixed Nonionic Surfactants and Isopropylmyristate
- Micellization and Interfacial Behaviour of Amitriptyline-Nonionic Surfactant Systems in Aqueous Medium
- Synthesis
- Ordered Ferrocene-containing Mesoporous Materials with Tailor-made Pore Size
- Cleaning Technology
- Comparison of Standards for Testing Electrical Dishwashers or Dishwashing Detergents
- Manual Dishwashing – How can it be Optimized?
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Environmental/Technical Chemistry
- Alkyl Polyglycoside-Sorbitan Ester Formulations for Improved Oil Recovery
- Novel Surfactants
- Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants
- Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery
- Physical Chemistry
- Dynamics of Formation of Vesicles Studied by Highly Time-resolved Stopped-flow Experiments
- Ion Extractant as Cosurfactant at the Water-Oil Interface in Microemulsions
- Microemulsions with Mixed Nonionic Surfactants and Isopropylmyristate
- Micellization and Interfacial Behaviour of Amitriptyline-Nonionic Surfactant Systems in Aqueous Medium
- Synthesis
- Ordered Ferrocene-containing Mesoporous Materials with Tailor-made Pore Size
- Cleaning Technology
- Comparison of Standards for Testing Electrical Dishwashers or Dishwashing Detergents
- Manual Dishwashing – How can it be Optimized?