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malcolm

hydrophobic AND hydrophilic

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does anyone know of molecules that include both hydrophobic and hydrophilic groups, besides phospholipids?

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A lot of detergents/surfactants, such as sodium dodecyl sulfate and octyl glucoside, are used to simulate phospholipids in biochemical experiments.

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Ethyl alcohol, acetate are a couple of examples. Phospho-Lipids are also both, if one includes their negatively charged tails. The hydrophilic moieties interact with the hydrogen bonding of water to help lower the aqueous hydrogen bonding potental. While hydrophobic moieties interact with the hydrogen bonding of water to increase the aqueous hydrogen bonding potential. Small bi-functional molecules, like ethyl alcohol do both to create intermediate hydrogen bonding affects within the water.

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The general name ofr such materials is amphiphiles.

 

Another formulation of amphiphiles is block copolymers. That is a hydrophobic and a hydrophilic polymer that are joined together end to end, such as polyethylene glycol and poly(ethylene oxide). They are of great interest as vehicles for drug delivery within the body as they form small micelles (highly controllable sizes from 20 to 200nm across) that are relatively non-immunogenic. (See, for example, Gaucher et al 2005)

 

Similarly, proteins have been synthesized with long hydrophobic 'tails' of lipids to make self assembling nanoscale objects (see Hartgerink et al, PNAS 2002

and the same can be done to DMA molecules (Hsu et al, Langmuir 2005)

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