A conjugate of decyltriphenylphosphonium with plastoquinone can carry cyclic adenosine monophosphate,but not cyclic guanosine monophosphate,across artificial and natural membranes |
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Institution: | 1. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow 119991, Russia;2. Department of Bioengineering and Bioinformatics, Lomonosov Moscow State University, Moscow 119991, Russia;3. Department of Chemistry, Lomonosov Moscow State University, Moscow 119991, Russia;4. Department of Pharmacology, University of Washington, Seattle, USA |
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Abstract: | The present study demonstrated for the first time the interaction between adenosine 3′,5′-cyclic monophosphate (cAMP), one of the most important signaling compounds in living organisms, and the mitochondria-targeted antioxidant plastoquinonyl-decyltriphenylphosphonium (SkQ1). The data obtained on model liquid membranes and human platelets revealed the ability of SkQ1 to selectively transport cAMP, but not guanosine 3′,5′-cyclic monophosphate (cGMP), across both artificial and natural membranes. In particular, SkQ1 elicited translocation of cAMP from the source to the receiving phase of a Pressman-type cell, while showing low activity with cGMP. Importantly, only conjugate with plastoquinone, but not dodecyl-triphenylphosphonium, was effective in carrying cAMP. In human platelets, SkQ1 also appeared to serve as a carrier of cAMP, but not cGMP, from outside to inside the cell, as measured by phosphorylation of the vasodilator stimulated phosphoprotein. The SkQ1-induced transfer of cAMP across the plasma membrane found here can be tentatively suggested to interfere with cAMP signaling pathways in living cells. |
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