Multipotential Electrochemical Detection of Primer Extension Reactions on DNA Self-Assembled Monolayers

Giusto, Daniel A. Di; Wlassoff, Wjatschesslaw A.; Giesebrecht, Susanne; Gooding, J. Justin; King, Garry C.

doi:10.1021/ja0319036

Cited by 96 publications

(87 citation statements)

References 21 publications

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“…Recently, several types of modified DNA bearing diverse groups, for example, aminoalkynyl or aminoalkyl [4 6] and several types of attached functional molecules, for example, biotin, [6] acridones, [7] fer rocene, [8] amino acids, [9] carbohydrates, [10] or fluorescein labels, [11] have been prepared from the corresponding modi fied dNTPs by this methodology. The dNTP building blocks are usually prepared [4 9] by troublesome and laborious tri phosphorylation of the corresponding modified nucleosides, in which the functional groups usually have to be protected and deprotected.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Method for the Construction of Functionalized DNA Bearing Amino Acid Groups through Cross‐Coupling Reactions of Nucleoside Triphosphates Followed by Primer Extension or PCR

Čapek¹,

Cahová²,

Pohl³

et al. 2007

Chemistry A European J

135

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Single‐step aqueous cross‐coupling reactions of nucleobase‐halogenated 2′‐deoxynucleosides (8‐bromo‐2′‐deoxyadenosine, 7‐iodo‐7‐deaza‐2′‐deoxyadenosine, or 5‐iodo‐2′‐deoxy‐uridine) or their 5′‐triphosphates with 4‐boronophenylalanine or 4‐ethynylphenylalanine have been developed and used for efficient synthesis of modified 2′‐deoxynucleoside triphosphates (dNTPs) bearing amino acid groups. These dNTPs were then tested as substrates for DNA polymerases for construction of functionalized DNA through primer extension and PCR. While 8‐substituted adenosine triphosphates were poor substrates for DNA polymerases, the corresponding 7‐substituted 7‐deazaadenine and 5‐substituted uracil nucleotides were efficiently incorporated in place of dATP or dTTP, respectively, by Pwo (Pyrococcus woesei) DNA polymerase. Nucleotides bearing the amino acid connected through the less bulky acetylene linker were incorporated more efficiently than those directly linked through a more bulky phenylene group. In addition, combinations of modified dATPs and dTTPs were incorporated by Pwo polymerase. Novel functionalized DNA duplexes bearing amino acid moieties were prepared by this two‐step approach. PCR can be used for amplification of duplexes bearing large number of modifications, while primer extension is suitable for introduction of just one or several modifications in a single DNA strand.

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Section: Introductionmentioning

confidence: 99%

An Efficient Method for the Construction of Functionalized DNA Bearing Amino Acid Groups through Cross‐Coupling Reactions of Nucleoside Triphosphates Followed by Primer Extension or PCR

Čapek¹,

Cahová²,

Pohl³

et al. 2007

Chemistry A European J

135

View full text Add to dashboard Cite

show abstract

“…In this direction several approaches for multipotential labeling of DNA had been explored including formats based on different inorganic colloid nanocrystal tracers [8], on the use of different enzyme tags liberating products with different redox potentials [9] or simple organic tags such as aromatic amines or nitro compounds exhibiting distinct electrochemical activity [10]. Ferrocene derivatives with different electrochemical characteristics have been also used for that purpose [11].…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2009

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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.

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“…To produce a mixed monolayer surface, Fc ss-DNA capture probes and MCH were immobilized on an Au electrode. MCH has been used as a spacer to minimize nonspecific binding and maximize the efficiency of hybridization of capture and target probes [17,18]. Next, the immobilized Fc ss-DNA capture probes were hybridized with various target DNAs, after which the hybridized electrode surface was incubated with S1 nuclease to discriminate between PM, NC, and SBM target DNA.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical DNA Hybridization Detection Using DNA Cleavage

2008

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We report the new method for detection of DNA hybridization using enzymatic cleavage. The strategy is based on that S1 nuclease is able to specifically cleave only single strand DNA, but not double strand DNA. The capture probe DNA, thiolated single strand DNA labeled with electroactive ferrocene group, was immobilized on a gold electrode. After hybridization of target DNA of complementary and noncomplementary sequences, nonhybridized single strand DNA was cleaved using S1 nuclease. The difference of enzymatic cleavage on the modified gold electrode was characterized by cyclic voltammetry and differential pulse voltammetry. We successfully applied this method to the sequence-selective discrimination between perfectly matched and mismatched target DNA including a single-base mismatched target DNA. Our method does not require either hybridization indicators or other exogenous signaling molecules which most of the electrochemical hybridization detection systems require.

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Multipotential Electrochemical Detection of Primer Extension Reactions on DNA Self-Assembled Monolayers

Cited by 96 publications

References 21 publications

An Efficient Method for the Construction of Functionalized DNA Bearing Amino Acid Groups through Cross‐Coupling Reactions of Nucleoside Triphosphates Followed by Primer Extension or PCR

An Efficient Method for the Construction of Functionalized DNA Bearing Amino Acid Groups through Cross‐Coupling Reactions of Nucleoside Triphosphates Followed by Primer Extension or PCR

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

Electrochemical DNA Hybridization Detection Using DNA Cleavage

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