Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates

Gevorg Sargsyan; Brianna L. MacLeod; Urice Tohgha; Milan Balaz

doi:10.1016/j.tet.2012.01.021

Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates

Gevorg Sargsyan, Brianna L. MacLeod, Urice Tohgha, Milan Balaz

Integrated Sciences and Engineering Division

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

Circular dichroism (CD), UV-vis absorption, fluorescence, and resonance light scattering (RLS) spectroscopies were used to elucidate the role of the DNA sequence, linkers between DNA and porphyrin, and metal in the porphyrin coordination center on the self-assembly of DNA-porphyrin conjugates. A series of eight non-self-complementary DNA-porphyrin conjugates have been synthesized with zinc and free-base porphyrins covalently attached to the short ODNs (A ₈ or T ₈) via amide or phosphate linker. A small structural modification (e.g., amide linker replaced by the phosphate linker) showed a dramatic effect on the aggregation properties of DNA-porphyrin conjugates and greatly altered their spectroscopic properties. At low ionic strength, porphyrin aggregation was not observed for any conjugate. An increase in the ionic strength caused two out of eight conjugates to form chiral porphyrin dimers.

Original language	English
Pages (from-to)	2093-2099
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	9
DOIs	https://doi.org/10.1016/j.tet.2012.01.021
Publication status	Published - 2012 Mar 4

Bibliographical note

Funding Information:
M.B. thanks the UW start-up grant and the School of Energy Resources . G.S. thanks the School of Energy Resources Graduate Assistantship. B.L.M. was supported by the University of Wyoming NSF REU program .

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.01.021

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title = "Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates",

abstract = "Circular dichroism (CD), UV-vis absorption, fluorescence, and resonance light scattering (RLS) spectroscopies were used to elucidate the role of the DNA sequence, linkers between DNA and porphyrin, and metal in the porphyrin coordination center on the self-assembly of DNA-porphyrin conjugates. A series of eight non-self-complementary DNA-porphyrin conjugates have been synthesized with zinc and free-base porphyrins covalently attached to the short ODNs (A 8 or T 8) via amide or phosphate linker. A small structural modification (e.g., amide linker replaced by the phosphate linker) showed a dramatic effect on the aggregation properties of DNA-porphyrin conjugates and greatly altered their spectroscopic properties. At low ionic strength, porphyrin aggregation was not observed for any conjugate. An increase in the ionic strength caused two out of eight conjugates to form chiral porphyrin dimers.",

author = "Gevorg Sargsyan and MacLeod, {Brianna L.} and Urice Tohgha and Milan Balaz",

note = "Funding Information: M.B. thanks the UW start-up grant and the School of Energy Resources . G.S. thanks the School of Energy Resources Graduate Assistantship. B.L.M. was supported by the University of Wyoming NSF REU program . ",

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AU - Sargsyan, Gevorg

AU - MacLeod, Brianna L.

AU - Tohgha, Urice

AU - Balaz, Milan

N1 - Funding Information: M.B. thanks the UW start-up grant and the School of Energy Resources . G.S. thanks the School of Energy Resources Graduate Assistantship. B.L.M. was supported by the University of Wyoming NSF REU program .

PY - 2012/3/4

Y1 - 2012/3/4

N2 - Circular dichroism (CD), UV-vis absorption, fluorescence, and resonance light scattering (RLS) spectroscopies were used to elucidate the role of the DNA sequence, linkers between DNA and porphyrin, and metal in the porphyrin coordination center on the self-assembly of DNA-porphyrin conjugates. A series of eight non-self-complementary DNA-porphyrin conjugates have been synthesized with zinc and free-base porphyrins covalently attached to the short ODNs (A 8 or T 8) via amide or phosphate linker. A small structural modification (e.g., amide linker replaced by the phosphate linker) showed a dramatic effect on the aggregation properties of DNA-porphyrin conjugates and greatly altered their spectroscopic properties. At low ionic strength, porphyrin aggregation was not observed for any conjugate. An increase in the ionic strength caused two out of eight conjugates to form chiral porphyrin dimers.

AB - Circular dichroism (CD), UV-vis absorption, fluorescence, and resonance light scattering (RLS) spectroscopies were used to elucidate the role of the DNA sequence, linkers between DNA and porphyrin, and metal in the porphyrin coordination center on the self-assembly of DNA-porphyrin conjugates. A series of eight non-self-complementary DNA-porphyrin conjugates have been synthesized with zinc and free-base porphyrins covalently attached to the short ODNs (A 8 or T 8) via amide or phosphate linker. A small structural modification (e.g., amide linker replaced by the phosphate linker) showed a dramatic effect on the aggregation properties of DNA-porphyrin conjugates and greatly altered their spectroscopic properties. At low ionic strength, porphyrin aggregation was not observed for any conjugate. An increase in the ionic strength caused two out of eight conjugates to form chiral porphyrin dimers.

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DO - 10.1016/j.tet.2012.01.021

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JO - Tetrahedron

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Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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