Metallacarboranes as redox labels in voltammetric methods of DNA determination

Justyna W. Janusik 1Elzbieta Malinowska 1Łukasz B. Górski 1Agnieszka Olejniczak 2

1. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, Warszawa 00-664, Poland
2. Institute for Medical Biology, Polish Academy of Sciences, Łódź 93-232, Poland

Abstract

There are a lot of different DNA labels [1]. Over last years also boron clusters and metallacarboranes were proposed for the labelling of DNA [2]. Metallabarboranes are vast family of metalocene-type complexes consisting of at least one carborane cage ligand and one or more metal atoms. Many of them undergo reversible chemical or electrochemical oxidation and reduction [3]. This work is a part of the project which aims at the construction of DNA biosensor with voltammetric detection. Electrochemical detection is possible due to metallacarboranes application as a redox labels of DNA.

The goal of this work was:

· Synthesis of 2’-deoxyadenosine – metallacarborane conjugates containing iron or chromium (6-N-{5-[(3,3’-iron-1,2,1’,2’-dicarbollide)8-yl]-3-oxapentoxy}-2’-deoxyadenosine (4) and -N-{5-[(3,3’-chrom-1,2,1’,2’-dicarbollide)8-yl]-3-oxapentoxy}-2’-deoxyadenosine (5)) [4, 5].

· Redox activity investigations of compound 4 and 5 using voltammetric methods. Selection of compound with better electrochemical properties to the oligonucleotide – metallacarborane conjugate synthesis.

In the first steps of synthesis, compounds 4 and 5 were obtained. Next, electrochemical investigations were performed.  Results allowed to choose compound bearing iron ion (4) as a potential nucleic acid redox label. Compund 4 was used in the next steps of synthesis in which H-phosphonate derivative was obtained (5’-O-dimethoxytrityl 6-N-{5-[(3,3’-iron-1,2,1’,2’-dicarbollide)8-yl]-3-oxapentoxy}-2’-deoxyadenosine 3’-O-(H-phosphonate)) (7). H-phosphonate derivative was used in an trial of oligonucleotide – metallacarborane conjugate synthesis.

Literature:

1. Teles, F.R.R. and L.P. Fonseca, Trends in DNA biosensors. Talanta, 2008. 77(2): p. 606-623.

2. Olejniczak, A.B., J. Plešek, and Z.J. Leśnikowski, Nucleoside-metallacarborane conjugates for base-specific metal labeling of DNA. Chemistry - A European Journal, 2007. 13(1): p. 311-318.

3. Olejniczak, A.B., Karborany i metalokarborany. Część II. Metalokarborany. Wiadomości Chemiczne, 2005.

4. Olejniczak, A.B., et al., DNA-Dinucleotides Bearing a 3,3'-Cobalt- Or 3,3'-Iron-1,2,1',2'-dicarbollide Complex. Organometallics, 2007. 26(14): p. 3272-3274.

5. Olejniczak, A.B., et al., Metallacarboranes as labels for multipotential electrochemical coding of DNA. [3-Chromium bis(dicarbollide)](-1)ate and its nucleoside conjugates. Electroanalysis, 2009. 21(3-5): p. 501-506.

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Presentation: Poster at SMCBS'2009 International Workshop, by Justyna W. Janusik
See On-line Journal of SMCBS'2009 International Workshop

Submitted: 2009-10-21 14:30
Revised:   2009-10-29 13:21
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