Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2093-2099
Number of pages7
JournalTetrahedron
Volume68
Issue number9
DOIs
Publication statusPublished - 2012 Mar 4

Fingerprint

Dimerization
Porphyrins
DNA
Ionic strength
Amides
Osmolar Concentration
Agglomeration
Phosphates
DNA sequences
Circular Dichroism
Dimers
Light scattering
Self assembly
Zinc
Spectrum Analysis
Complementary DNA
Fluorescence
Metals
Spectroscopy
Light

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Sargsyan, Gevorg ; MacLeod, Brianna L. ; Tohgha, Urice ; Balaz, Milan. / Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates. In: Tetrahedron. 2012 ; Vol. 68, No. 9. pp. 2093-2099.
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Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates. / Sargsyan, Gevorg; MacLeod, Brianna L.; Tohgha, Urice; Balaz, Milan.

In: Tetrahedron, Vol. 68, No. 9, 04.03.2012, p. 2093-2099.

Research output: Contribution to journalArticle

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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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