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Biophys J, September 2001, p. 1501-1510, Vol. 81, No. 3

Characteristics of Pyrene Phospholipid/gamma -Cyclodextrin Complex

Kimmo Tanhuanpää,* Kwan Hon Cheng,dagger Krista Anttonen,* Jorma A. Virtanen,Dagger and Pentti Somerharju*

 *Institute of Biomedicine, Department of Biochemistry, University of Helsinki, Finland;  dagger Department of Physics, Texas Tech University, Lubbock, Texas 79409 USA; and  Dagger Institute of Chemistry, Department of Physical Chemistry, University of Helsinki, Finland

Recently, it was demonstrated that gamma -cyclodextrins (gamma -CDs) greatly accelerates transfer of hydrophobic pyrene-labeled and other fluorescent phospholipid derivatives from vesicles to cells in culture (Tanhuanpää and Somerharju, 1999). To understand better the characteristics of this process, we studied the interaction of gamma -CD with pyrene-labeled phosphatidylcholines (PyrPCs) using a variety of physical methods. Either one or both of the acyl chains of PC was labeled with a pyrene moiety (monoPyrPCs and diPyrPCs, respectively), and the length of the labeled chain(s) varied from 4 to 14 carbons. Fluorescent binding assays showed that the association constant decreases strongly with increasing acyl chain length. PyrPC/gamma -CD stoichiometry was 1:2 for the shorter chain species, but changed to 1:3 when the acyl chain length exceeded 8 (diPyrPCs) or 10 (monoPyrPCs) carbons. The activation energy for the formation of diPyr10PC/gamma -CD complex was high, i.e., +92 kJ/mol, indicating that the phospholipid molecule has to fully emerge from the bilayer before complex formation can take place. The free energy, enthalpy, and entropy of transfer of monoPyrPC from bilayer to gamma -CD complex were close to zero. The absorption, Fourier transform infrared, and fluorescence spectral measurements and lifetime analysis indicated that the pyrene moiety lies inside the CD cavity and is conformationally restricted, particularly when the labeled chain is short. The acyl chains of a PyrPC molecule seem to share a CD cavity rather than occupy different ones. The present data provide strong evidence that the ability of gamma -CD to enhance intermembrane transfer of pyrene-labeled phospholipids is based on the formation of stoichiometric complexes in the aqueous phase. This information should help in designing CD derivatives that are more efficient lipid carriers then those available at present.

Biophys J, September 2001, p. 1501-1510, Vol. 81, No. 3
© 2001 by the Biophysical Society   0006-3495/01/09/1501/10  $2.00


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