Bolaamphiphile quinone

Similar results were obtained when the zinc porphyrin was bound to the outer vesicle surface and a quinone bolaamphiphile was integrated within a DHP or DODAB vesicle membrane. The quenching constant of the porphy-... 

The anthraquinone-based bolaphile 7 or 8 could not form homogeneous membranes due to steric interactions (Scheme 3) however, they could be integrated into host membranes formed by dihexadecylphosphate and dime-thyldioctadecylammonium bromide. The bolaamphiphile fixed the quinone functionality in the center of the membrane and served as a model for pool quinones. [20] Electron transfer was further demonstrated by light-induced charge transfer between cationic porphyrins dissolved in water and membrane-bound anthraquinone bolaphiles. [27]... 

The nucleophilic reactivity of cysteine has been exploited in Michael reactions with quinones. One example is a water-soluble naphthoquinone, which has been entrapped in chlorophyll-containing vesicles in order to study light-induced electron transfer through a membrane from glutathione to the quinone (Fore, 1983). Another example is an asymmetrical vesicle membrane made of a cysteine quinone carboxylate bolaamphiphile, where all the quinone is localized on the outer surface of the vesicle (see Scheme 7.2.6 Scheme 9.5.1). 

Fuhrhop, J.-H., Hungerbiihler, H., Siggel, U. (1990). Quinone containing amphiphiles and bolaamphiphiles, which form redoxactive lipid membranes, Langmuir 6 1295. 

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