Wiley Encyclopedia of Chemical Biology 2008
DOI: 10.1002/9780470048672.wecb654
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DNA‐Conjugated Organic Chromophores inDNAStacking Interactions

Abstract: Since the discovery of the intercalation of acridine derivatives into DNA (1961), chemists have synthesized many intercalators tethered to DNA. Advances in the chemical synthesis of modified nucleosides along with progress in oligonucleotide synthesis have made it possible to introduce organic chromophores in any desired position of the sequence. As an outcome of such fascinating research, we gained a deeper knowledge and understanding of nucleic acid structures, which is pivotal for future progress within nuc… Show more

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Cited by 27 publications
(31 citation statements)
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“…Intercalating agents share some common structural features, such as the presence of planar polyaromatic systems that are inserted between DNA base-pairs with a marked preference for 5′-pyrimidine-purine-3′ sequence. In addition, the chromophores are linked to basic moieties that might also play an important role in the affinity and selectivity shown for compounds [1215]. …”
Section: Introductionmentioning
confidence: 99%
“…Intercalating agents share some common structural features, such as the presence of planar polyaromatic systems that are inserted between DNA base-pairs with a marked preference for 5′-pyrimidine-purine-3′ sequence. In addition, the chromophores are linked to basic moieties that might also play an important role in the affinity and selectivity shown for compounds [1215]. …”
Section: Introductionmentioning
confidence: 99%
“…For delocalized excitation, a high structural order of the individual chromophores is a prerequisite. [7,[23][24][25][26][27][28][29][30][31][32][33] The formation of chromophore segments that are welldefined with regard to the number and kind of the components is readily controlled by hybridization of complementary strands. [4,[19][20][21][22] DNA has been used as a supramolecular scaffold for the construction of distinct arrays of aromatic dyes.…”
mentioning
confidence: 99%
“…R f = 0.24 (petroleum ether/EtOAc, 3:1). 1 122.85, 123.33, 124.58, 124.69, 124.73, 124.94, 125.69, 126.47, 127.12, 127.15, 127.43, 127.63, 127.69, 128.37, 128.54, 129.70, 130.82, 131.33, 136. …”
Section: Preparation Of (S)-1-(benzyloxy)-5-(pyren-1-yl)pentan-2-ol (5)mentioning
confidence: 99%
“…[1] One of the most promising candidates for the intercalating moiety is pyrene because it has almost the same surface area as a regular Watson-Crick base pair, which makes a large stabilization through base stacking with neighboring base pairs. [2] Another advantage is that pyrene is a fluorescent molecule and if two pyrene residues come close together (3-5 Å ) the formation of an excimer band is possible.…”
Section: Introductionmentioning
confidence: 99%