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Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery

  • Q.-R. Yang , W.-H. Qiao , S.-M. Zhang , J.-P. Qu and D.-L. Liu
Published/Copyright: April 5, 2013
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 47 Issue 5

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.

Key words:: Synthesis; Gene delivery; Carbamate; Cationic galactolipid; Surface tension
Stichwörter:: Synthese; Gentransferprozess; Carbamat; kationisches Galactolipid; Oberflächenspannung
∗ Dr. Wei-hong Qiao, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, China. E-Mail:

Qingrui Yang was born in 1986. He obtained his Bachelor's Degree from Shandong University of Science and Technology in 2008. He is now taking a masters degree in the synthesis and physical chemistry of surfactants at Dalian University of Technology.

Weihong Qiao was born in 1968. She obtained a Master's Degree from Dalian University of Technology in 1994 and a Ph.D. from the same university in 2000. Since 1994, she has been teaching and working at Dalian University of Technology. Her main field of research is the synthesis of surfactants.

Shumin Zhang was born in 1983. He obtained his Bachelor's Degree from Qingdao University of Science and Technology in 2007. He is now taking a masters degree in the synthesis and physical chemistry of surfactants at Dalian University of Technology.

Jingping Qu was born in 1960. He obtained a Master's Degree from Dalian University of Technology in 1988 and a PhD from the University of Tokyo in 1996. He worked at Mitsubishi Chemical Corporation in Japan before 2004. Since 2004, he has been teaching and working at Dalian University of Technology. His main field of research is the asymmetric synthesis.

Dongliang Liu was born in 1971. He obtained his Bachelor's Degree from Dalian University of Technology in 1997 and a PhD from the same university in 2006. Since 2006, he been teaching and working at Donghua University.

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Received: 2010-03-03
Published Online: 2013-04-05
Published in Print: 2010-09-01

© 2010, Carl Hanser Publisher, Munich

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https://doi.org/10.3139/113.110080
Keywords for this article
Synthesis; Gene delivery; Carbamate; Cationic galactolipid; Surface tension

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Environmental/Technical Chemistry
  6. Alkyl Polyglycoside-Sorbitan Ester Formulations for Improved Oil Recovery
  7. Novel Surfactants
  8. Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants
  9. Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery
  10. Physical Chemistry
  11. Dynamics of Formation of Vesicles Studied by Highly Time-resolved Stopped-flow Experiments
  12. Ion Extractant as Cosurfactant at the Water-Oil Interface in Microemulsions
  13. Microemulsions with Mixed Nonionic Surfactants and Isopropylmyristate
  14. Micellization and Interfacial Behaviour of Amitriptyline-Nonionic Surfactant Systems in Aqueous Medium
  15. Synthesis
  16. Ordered Ferrocene-containing Mesoporous Materials with Tailor-made Pore Size
  17. Cleaning Technology
  18. Comparison of Standards for Testing Electrical Dishwashers or Dishwashing Detergents
  19. Manual Dishwashing – How can it be Optimized?
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