Collect. Czech. Chem. Commun. 2008, 73, 175-186

Highly Lipophilic p-Carborane-Modified Adenosine Phosphates

Blazej A. Wojtczak, Agnieszka B. Olejniczak, Marzena PrzepiĆ³rkiewicz, Agnieszka Andrysiak and Zbigniew J. Lesnikowski*

Centre of Medical Biology, Laboratory of Molecular Virology and Biological Chemistry, Polish Academy of Sciences, 106 Lodowa St., 93-232 Lodz, Poland


The method was developed for the synthesis of biologically important adenosine phosphates, AMP, cAMP and ATP modified with p-carborane cluster - a highly lipophilic pharmacophore. The adenosine phosphates modified with p-carborane are characterized by increased stability in human blood plasma and much more higher lipophilicity than that of the unmodified phosphates. ATP analog 4 bearing p-carborane cluster is not a Taq polymerase substrate and most probably not the polymerase inhibitor. These properties may have clinical implications.

Keywords: Carboranes; Pharmacophores; Nucleosides; Nucleotides; Adenosine phosphates; AMP; cAMP; ATP; Lipophilicity; PCR; Nucleoside triphosphates; Polymerase incorporation.

References: 24 live references.