Synthesis, DNA binding and photocleavage study of novel anthracene-appended macrocyclic polyamines

Abstract

Two anthracene derivatives appended on cyclen (1,4,7,10-tetraazacyclododecane) moieties were synthesized and characterized. In these new compounds, the anthryl is used as a substitute for the nucleobases of classical PNA backbone, and the cyclen moiety appends on the terminal amino group. The interaction of the compounds with DNA was systematically investigated by absorption, fluorescence, and viscometric titration, DNA melting and gel electrophoresis experiments. From the absorption titration data, bis-anthryl compound can bind to CT DNA with K(b) = 1.21 x 10(5) M(-1) that is 121 times larger than that of mono-anthryl compound (K(b) = 1.00 x 10(3) M(-1)). Through the fluorescence titration data, compound shows distinct CG-selective DNA binding activity. DNA melting and viscometric titration experiments indicate that the binding mode of is a multiple binding mode that involves groove binding and partial intercalation. Compound also shows excellent DNA photocleavage ability, which is much more efficient than the mono-anthryl compound .

Off–on–off pH luminescence switching and DNA binding properties of a free terpyridine-appended ruthenium complex

“…[60], and falls into the rather broad ΔT m range of 5.9 to 19.3°C previously reported for analogous Ru(II) complex-based DNA intercalators under identical experimental conditions with [Ru]/DNA = 0.10 [37][38][39][40][41][42][43][44][45]. In addition, this ΔT m value is similar to a ΔT m value of 9.3°C that we have recently reported for a Ru(II) complex DNA binder with a mixed binding mode involving classic intercalation plus partial intercalation [23], and greater than only small T m increases of ≤ 2 and 3°C previously reported for an organic DNA binder of 1,4,7,10-tetraazacyclododecane appended with two anthracenyl moieties that showed mixed binding modes of partial intercalator and groove binding [61], and partially intercalative Ru(II) complex of [Ru(H 2 PDTA)(phen)]Cl (H 4 PDTA = propylene-1,2-diaminetetra-acetic acid) [32], respectively.…”

Cooperative DNA Compaction by Ternary Supramolecular Complex with Cucurbituril/Cyclodextrin Pair

“…As discerned from Figures S13 and , in our case, no obvious change was found in the circular dichroism spectra of DNA with excess amount of 1 ⋅CB[6] complex, and the specific viscosity of DNA was slightly declined in the presence of 1 and 1 ⋅CB[6] complex. These results are indicative of a nonintercalative mode in the DNA compaction with 1 ⋅CB[6] complex and provide evidence on their groove binding nature . Furthermore, it was also observed that DNA could be rapidly flocculated at the relatively higher concentrations of 1 ⋅CB[6] and 1 ⋅ 2 ⋅CB[6] systems, here again corroborating the good DNA condensation ability of CB[6]‐involved complexes (Figure S14 in the Supporting Information).…”

Interaction of bis-aryl functionalized molecules with nucleosides and nucleic acids

“…N-tert-butyloxycarbonyl-1,2-diaminoethane [26] and [4,7,10-tris(tertbutoxy-carbonyl)-1,4,7,10-tetraaza-cyclododecan-1-yl]acetic acid (Scheme 1, triBoc-cyclen-acetic acid ) were synthesized according to the literature [27]. Compound 1c was synthesized and characterized in our previous work [25]. The CT DNA which was purchased from sigma was directly dissolved in water at a concentration of 1 mg/mL and stored at 4°C.…”

“…The preparation of designed target compounds 1 was performed based on our previous studies [25]. As shown in Scheme 1, compounds 3 were obtained by reduction of the Schiff base formed by N-Boc-1,2-diaminoethane and relative aldehydes.…”

“…In previous studies, we investigated the large difference in DNA binding and cleavage abilities between two anthracene derivatives [25], in which the only structure difference was the anthracene units. The binding and cleavage abilities of the anthracene dimer ( Figure 1, compound 1c) are more than twice of those indicated by the monomer.…”