The synthesis and nucleic acid interactions of an acridine-porphyrin heterodimer.
Item
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Title
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The synthesis and nucleic acid interactions of an acridine-porphyrin heterodimer.
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Identifier
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AAI9417505
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identifier
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9417505
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Creator
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Scarborough, Alex Laon.
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Contributor
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Adviser: David K. Lavallee
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Date
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1994
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Biochemistry | Chemistry, Organic
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Abstract
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Two nucleic acid-interacting compounds were synthesized; binding modes on DNA were evaluated by circular dichroism, UV-visible absorption and fluorescence spectroscopy; equilibrium constants for binding were determined by ethidium bromide competitive binding.;The indicated mode of binding of meso- (tetra(N- (tri-methylammoniumethyl) -4-benzamidyl)) porphine (TAP) to poly(dA-dT) {dollar}\cdot{dollar} (dA-dT) is non-intercalative, external binding. Interaction with poly(dG-dC) {dollar}\cdot{dollar} (dG-dC) is indicated to be by intercalation. With calf thymus DNA, there is a combination of the two modes.;A molecule with two domains capable of nucleic acid interactions, an acridine-porphyrin heterodimer, 5- (4-(N- (9-acridinyl) -3-aminopropoxy)phenyl) -10,15,20-tri (4-(N- (tri-methylammoniumethyl))benzamidyl) porphine (ATB) produces CD, UV-visible and fluorescence emission spectra that are similar.;Equilibrium constants for binding to poly(dA-dT) {dollar}\cdot{dollar} (dA-dT), poly(dG-dC) {dollar}\cdot{dollar} (dG-dC) and calf thymus DNA reveal that TAP binds to the nucleic acids with strong affinities, while ATB has much weaker affinities. The data are consistent with a mode of binding for ATB that is dominated by an intercalated acridine moiety and an externally bound porphyrin macrocycle.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
