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Freiburger Materialforschungszentrum
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You are here: Home Events Dr. Andreas Zumbühl "Synthesis and Applications of Artificial Phospholipids"

Dr. Andreas Zumbühl "Synthesis and Applications of Artificial Phospholipids"

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Department of Organic Chemistry, University of Geneva, Switzerland

What
  • Seminar
When Dec 15, 2010
from 02:15 PM to 03:00 PM
Where “Hörsaal Makromolekulare Chemie”, Stefan-Meier-Str. 31, Freiburg
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We are interested in the organic synthesis of new phospholipids and the applications of lipids in Biology and Medicine.[1]

Nature is providing a wealth of thousands of chemically distinct lipid structures. However, a closer look at glycerophospholipids and sphingolipids reveals that this variety is mainly based on combinations of different head groups and tails. The backbone holding together the hydrophilic and hydrophobic parts is conserved and consists either of glycerol or 2-amino-1,3-propanol. Expanding the set of available backbone structures could allow chemistries that are not possible with natural phospholipids.

Here we introduce a 1,3-diaminopropanol backbone leading to diamido- and diaminophospholipids. Our synthetic strategy is diverse and is based on easily accessible, cheap P(III) and P(V) reagents such as benzyloxydichlorophosphine (BODP) or phosphorodichloridates.[2]

We show that both 1,3-diamido and 1,3-diaminophospholipis form vesicles under standard conditions and that an acrylamide substituted diaminophospholipid undergoes rapid UV polymerization to form giant vesosome-like structures.

Our group is also working on vesicles that release their cargo under increasing shear stress. This concept bears potential for the treatment of cardiovascular diseases and vesicle formulations are presented that differentiate between healthy and stenosed arteries.

[1] Zumbuehl, A. Nonnatural Phospholipids: Probing Nature's Modular Platform. Chimia 2009, 1, 63–65.
[2] I. A. Fedotenko; P. L Zaffalon; Favarger, F.; Zumbuehl, A. The Synthesis of 1, 3- Diamidophospholipids. Tetrahedron Letters 2010, 51, 5382-5384.

 

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