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
“…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 [12–15]. …”
A series of novel potential DNA bis-intercalators were designed and synthesized, in which two glucuronic acids were linked by ethylenediamine, and the glucuronic acid was coupled with various chromophores, including quinoline, acridine, indole and purine, at the C-1 position. The preliminary binding properties of these compounds to calf thymus DNA (CT-DNA) have been investigated by UV-absorption and fluorescence spectroscopy. The results indicated that all the target compounds can interact with CT-DNA, and the acridine derivative, 3b, showed the highest key selection vector (KSV) value, which suggested that compound 3b binds most strongly to CT-DNA.
“…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 [12–15]. …”
A series of novel potential DNA bis-intercalators were designed and synthesized, in which two glucuronic acids were linked by ethylenediamine, and the glucuronic acid was coupled with various chromophores, including quinoline, acridine, indole and purine, at the C-1 position. The preliminary binding properties of these compounds to calf thymus DNA (CT-DNA) have been investigated by UV-absorption and fluorescence spectroscopy. The results indicated that all the target compounds can interact with CT-DNA, and the acridine derivative, 3b, showed the highest key selection vector (KSV) value, which suggested that compound 3b binds most strongly to CT-DNA.
“…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.…”
The understanding and description of collectively excited multichromophores is of crucial importance for many areas of basic and applied research. DNA has been used for the construction of well-defined heterochromophoric stacks. Electronic coupling among non-adjacent chromophores of the same type leads to the co-existence of PDI and pyrene H-aggregates in hybrids composed of alternating chromophore stacks.
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.…”
We have synthesized a carbon linker analogue of INA (oligonucleotides containing insertions of 1-O-(1-pyrenylmethyl)glycerol). Thermal stability studies showed an increase in melting temperature in favor of the carbon linker analogue. We also synthesized a carbon linker analogue with two pyrenes geminally attached. Fluorescence studies of this intercalating nucleic acid with the pyrene moieties inserted as a bulge showed formation of an excimer band. When a mismatch was introduced at the site of the intercalator, an excimer band was formed for the destabilized duplexes whereas an exciplex band was observed when the stability of the duplex was retained.
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