Metallacarboranes as Labels for Multipotential Electrochemical Coding of DNA. [3‐Chromium bis(dicarbollide)](‐1)ate and Its Nucleoside Conjugates

Abstract

Metallacarborane bearing chromium is proposed as the electrochemical label for electrochemical coding of DNA. Synthesis and HDV characteristics of 2'-deoxyadenosine (dA) containing [(3,3'-chromium-1,2,1',2'-dicarbollide)] (À 1)]ate complex are described. The proposed labeling of nucleosides, together with previously described nucleoside/ metallacarborane conjugates bearing cobalt and iron lay the foundations for multipotential electrochemical coding of DNA with metallacarborane complexes and simultaneous detection of several DNA targets.

DNA probe modified with 3-iron bis(dicarbollide) for electrochemical determination of DNA sequence of Avian Influenza Virus H5N1

“…Working in this very vivid research field, we decided to use an alternative type of redox label, namely the chemically and biologically stable complex of carborane with Fe(III) with well-defined electrochemical properties (Corsini et al, 2006;Jelen et al, 2009;Olejniczak et al, 2009;Olejniczak 2011). Metallacarboranes are vast family of metallocenetype complexes consisting of at least one carborane cage and one or more metal cations.…”

Interaction of Adenosine, Modified Using Carborane Clusters, with Ovarian Cancer Cells: A New Anticancer Approach against Chemoresistance

“…The ring cleavage of 8-dioxane-[3,3 -chroma bis(1,2-dicarbollide)] ( 7) was shown by our group in previously published works [23,35]; however, its synthesis and characteristics are described for the first time herein (Scheme 2), inclusive of its molecular structure (Figure 13 with the description below). The reaction was performed analogously to the procedure described above with the exception that [3,3 -chromma-bis(1,2-dicarba-closoundecaborate](-1)ate (3) was reacted with dioxane in the presence of BF 3 .…”

“…Metallacarboranes and carboranes have been identified as promising therapeutically important compounds [20][21][22][23][24] including boronated nucleosides that have been extensively studied in recent years [25][26][27][28]. Several approaches have been previously proposed by us for the synthesis of adenosine and 2 -deoxyadenosine derivatives modified with boron clusters (carboranes and metallacarboranes) [29][30][31][32][33][34][35][36][37][38].…”

A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

“…Boron-containing nucleosides were originally designed as potential boron carriers for the boron neutron capture therapy (BNCT) of tumours [1]. Recently several other applications of nucleosideeboron cluster conjugates have been proposed, including RedOx-labels [2], IR-labels [3], modulators of the purinergic receptors activity or inhibitors of the blood platelets aggregation [4]. Thus, in last three decades a range of boronated nucleosides bearing boronic acids residue as well as boron clusters have been synthesized and tested [5,6].…”