Synthesis and characterization of porphyrin-DNA constructs for the self-assembly of modular energy transfer arrays

Nathaniel T. Anderson; Peter H. Dinolfo; Xing Wang

doi:10.1039/c7tc05272c

Synthesis and characterization of porphyrin-DNA constructs for the self-assembly of modular energy transfer arrays

Nathaniel T. Anderson, Peter H. Dinolfo, Xing Wang

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Abstract

In this report, a 5′ azide-terminated single-stranded DNA (ssDNA) was covalently attached to a Zn-tetra(phenylethynyl)porphyrin (ZnTPEP) utilizing copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) to form five DNA-porphyrin adducts containing one to four ssDNAs attached around the porphyrin core. The newly synthesized DNA-porphyrin adducts provide a modular platform that allows us to assemble donor-acceptor energy transfer (EnT) arrays/constructs using complementary dye-labeled ssDNAs, herein a 3′ AlexaFluor 546 (A546)-labeled ssDNA, with different donor:acceptor ratios. The photophysical properties of the DNA-porphyrin constructs, along with the individual donor and acceptor fluorophores, were investigated by electronic absorption and steady-state emission spectroscopy. The data shows that A546 (donor) emission spectrum is significantly quenched in each of the constructs with EnT efficiencies that are comparable to the predicted EnT determined through modeling the Förster resonance energy transfer (FRET) mechanism.

Original language	English (US)
Pages (from-to)	2452-2459
Number of pages	8
Journal	Journal of Materials Chemistry C
Volume	6
Issue number	10
DOIs	https://doi.org/10.1039/c7tc05272c
State	Published - 2018
Externally published	Yes

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Chemistry(all)
Materials Chemistry

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10.1039/c7tc05272c

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title = "Synthesis and characterization of porphyrin-DNA constructs for the self-assembly of modular energy transfer arrays",

abstract = "In this report, a 5′ azide-terminated single-stranded DNA (ssDNA) was covalently attached to a Zn-tetra(phenylethynyl)porphyrin (ZnTPEP) utilizing copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) to form five DNA-porphyrin adducts containing one to four ssDNAs attached around the porphyrin core. The newly synthesized DNA-porphyrin adducts provide a modular platform that allows us to assemble donor-acceptor energy transfer (EnT) arrays/constructs using complementary dye-labeled ssDNAs, herein a 3′ AlexaFluor 546 (A546)-labeled ssDNA, with different donor:acceptor ratios. The photophysical properties of the DNA-porphyrin constructs, along with the individual donor and acceptor fluorophores, were investigated by electronic absorption and steady-state emission spectroscopy. The data shows that A546 (donor) emission spectrum is significantly quenched in each of the constructs with EnT efficiencies that are comparable to the predicted EnT determined through modeling the F{\"o}rster resonance energy transfer (FRET) mechanism.",

author = "Anderson, {Nathaniel T.} and Dinolfo, {Peter H.} and Xing Wang",

note = "Funding Information: This work was supported by Rensselaer Polytechnic Institute through new faculty start-up funds and the National Science Foundation under Contract No. CHE-1255100. N. T. A. acknowledges a Slezak Memorial Fellowship from Rensselaer Polytechnic Institute. We would also like to acknowledge the support of the Center for Biotechnology and Interdisciplinary Studies Research Core facilities and specifically Analytical Biochemistry Core director Joel Morgan for his assistance and guidance on this work. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2018.",

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doi = "10.1039/c7tc05272c",

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AU - Anderson, Nathaniel T.

AU - Dinolfo, Peter H.

AU - Wang, Xing

N1 - Funding Information: This work was supported by Rensselaer Polytechnic Institute through new faculty start-up funds and the National Science Foundation under Contract No. CHE-1255100. N. T. A. acknowledges a Slezak Memorial Fellowship from Rensselaer Polytechnic Institute. We would also like to acknowledge the support of the Center for Biotechnology and Interdisciplinary Studies Research Core facilities and specifically Analytical Biochemistry Core director Joel Morgan for his assistance and guidance on this work. Publisher Copyright: © The Royal Society of Chemistry 2018.

PY - 2018

Y1 - 2018

N2 - In this report, a 5′ azide-terminated single-stranded DNA (ssDNA) was covalently attached to a Zn-tetra(phenylethynyl)porphyrin (ZnTPEP) utilizing copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) to form five DNA-porphyrin adducts containing one to four ssDNAs attached around the porphyrin core. The newly synthesized DNA-porphyrin adducts provide a modular platform that allows us to assemble donor-acceptor energy transfer (EnT) arrays/constructs using complementary dye-labeled ssDNAs, herein a 3′ AlexaFluor 546 (A546)-labeled ssDNA, with different donor:acceptor ratios. The photophysical properties of the DNA-porphyrin constructs, along with the individual donor and acceptor fluorophores, were investigated by electronic absorption and steady-state emission spectroscopy. The data shows that A546 (donor) emission spectrum is significantly quenched in each of the constructs with EnT efficiencies that are comparable to the predicted EnT determined through modeling the Förster resonance energy transfer (FRET) mechanism.

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Synthesis and characterization of porphyrin-DNA constructs for the self-assembly of modular energy transfer arrays

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