Synthesis and evaluation of adenosine derivatives as A₁, A_2A, A_2B and A₃ adenosine receptor ligands containing boron clusters as phenyl isosteres and selective A₃ agonists.

ABSTRACT: A series of adenosine and 2'-deoxyadenosine pairs modified with a 1,12-dicarba-closo-dodecaborane cluster or alternatively with a phenyl group at the same position was synthesized, and their affinity was determined at A₁, A_2A, A_2B and A₃ adenosine receptors (ARs). While AR affinity differences were noted, a general tendency to preferentially bind A₃ AR over other ARs was observed for most tested ligands. In particular, 5'-ethylcarbamoyl-N⁶-(3-phenylpropyl)adenosine (18), N⁶-(3-phenylpropyl)-2-chloroadenosine (24) and N⁶-(3-phenylpropyl)adenosine (40) showed nanomolar A₃ affinity (K_i 4.5, 6.4 and 7.5 nM, respectively). Among the boron cluster-containing compounds, the highest A

SUBMITTER: Bednarska-Szczepaniak K 

PROVIDER: S-EPMC8448983 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature