Bioorg Med Chem
Division of Natural and Applied Sciences and Department of Chemistry, Hope College, Holland, MI 49423, USA.
Published: July 2013
Orthogonally positioned diamino/dicationic polyamides (PAs) have good water solubility and enhanced binding affinity, whilst retaining DNA minor groove and sequence specificity compared to their monoamino/monocationic counterparts. The synthesis and DNA binding properties of the following diamino PAs: f-IPI (3a), f-IPP (4), f-PIP (5), and f-PPP (6) are described. P denotes the site where a 1-propylamino group is attached to the N1-position of the heterocycle. Binding of the diamino PAs to DNA was assessed by DNase I footprinting, thermal denaturation, circular dichroism titration, biosensor surface plasmon resonance (SPR), and isothermal titration calorimetry (ITC) studies. According to SPR studies, f-IPI (3a) bound more strongly (K(eq)=2.4×10(8) M(-1)) and with comparable sequence selectivity to its cognate sequence 5'-ACGCGT-3' when compared to its monoamino analog f-IPI (1). The binding of f-IPI (3a) to 5'-ACGCGT-3' via the stacked dimer motif was balanced between enthalpy and entropy, and that was quite different from the enthalpy-driven binding of its monoamino parent f-IPI (1). f-IPP (4) also bound more strongly to its cognate sequence 5'-ATGCAT-3' (K(eq)=7.4×10(6) M(-1)) via the side-by-side stacked motif than its monoamino analog f-IPP (2a). Although f-PPP (6) bound via a 1:1 motif, it bound strongly to its cognate sequence 5'-AAATTT-3' (K(eq)=4.8×10(7) M(-1)), 15-times higher than the binding of its monoamino analog f-PPP (2c), albeit f-PPP bound via the stacked motif. Finally, f-PIP (5) bound to its target sequence 5'-ATCGAT-3' as a stacked dimer and it has the lowest affinity among the diamino PAs tested (Keq <1×10(5) M(-1)). This was about two times lower in affinity than the binding of its monoamino analog f-PIP (2b). The results further demonstrated that the 'core rules' of DNA recognition by monoamino PAs also apply to their diamino analogs. Specifically, PAs that contain a stacked IP core structure bind most strongly (highest binding constants) to their cognate GC doublet, followed by the binding of PAs with a stacked PP structure to two degenerate AT base pairs, and finally the binding of PAs with a PI core to their cognate CG doublet.
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http://dx.doi.org/10.1016/j.bmc.2013.04.001 | DOI Listing |
Mater Today Chem
December 2019
Nanochemistry/QDs R & D Laboratory, Department of Applied Chemistry, Defence Institute of Advanced Technology (DIAT), Ministry of Defence, DRDO, Government of India, Girinagar, Pune, 411025, India.
Schiff bases are versatile organic compounds which are widely used and synthesized by condensation reaction of different amino compound with aldehydes or ketones known as imine. Schiff base ligands are considered as privileged ligands as they are simply synthesized by condensation. They show broad range of application in medicine, pharmacy, coordination chemistry, biological activities, industries, food packages, dyes, and polymer and also used as an O detector.
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February 2019
Functional Polymer Membranes Group, Advanced Membranes and Porous Materials Center, Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia.
A triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diamino-triptycene (TMDAT), was used for the synthesis of a novel solution-processable polyamide obtained via polycondensation reaction with 4,4'-(hexafluoroisopropylidene)bis(benzoic acid) (6FBBA). Molecular simulations confirmed that the tetrasubstitution with -methyl groups in the triptycene building block reduced rotations around the C⁻N bond of the amide group leading to enhanced fractional free volume. Based on N₂ sorption at 77 K, 6FBBA-TMDAT revealed microporosity with a Brunauer⁻Emmett⁻Teller (BET) surface area of 396 m² g; to date, this is the highest value reported for a linear polyamide.
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October 2017
Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Department of Macromolecular Science and Engineering, School of Chemical, Chemical Engineering and Materials, Heilongjiang University, Harbin 150086, China.
In this study, a new diamine monomer, namely 4,4'-diamino-4″-(5-dibenzo[]azepin-5-yl)triphenylamine, was prepared and polymerized with four kinds of dicarboxylic acids via direct polycondensation reaction resulting in a novel series of soluble and electroactive polyamides (PAs). The tough thin films of all PAs could be solution-cast onto an indium-tin oxide (ITO)-coated glass substrate owing to the good solubility in polar organic solvents. Two pairs of obvious redox peaks for these films were observed in cyclic voltammetry (CV) with low onset potentials () of 0.
View Article and Find Full Text PDFFront Plant Sci
December 2015
College of Agriculture/The Key Laboratory of Oasis Eco-Agriculture, Shihezi University Shihezi, China.
The objective of this study was to increase understanding about the mechanism by which polyamines (PAs) promote the conversion of embryogenic calli (EC) into somatic embryos in cotton (Gossypium hirsutum L.). We measured the levels of endogenous PAs and H2O2, quantified the expression levels of genes involved in the PAs pathway at various stages of cotton somatic embryogenesis (SE), and investigated the effects of exogenous PAs and H2O2 on differentiation and development of EC.
View Article and Find Full Text PDFPhys Chem Chem Phys
January 2016
School of Chemistry, Monash University, 17 Rainforest Walk, Clayton 3800, Australia.
Carbon dioxide (CO2) chemical absorption and regeneration was investigated in two diamino carboxylate protic ionic liquids (PILs), dimethylethylenediamine formate (DMEDAH formate) and dimethylpropylenediamine acetate (DMPDAH acetate), using novel calorimetric techniques. The PILs under study have previously been shown to possess a CO2 absorption capacity similar to the industrial standard, 30% aqueous MEA, while requiring much lower temperatures to release the captured CO2. We show that this is in part due to the fact that the PILs exhibit enthalpies of CO2 desorption as low as 40 kJ mol(-1), significantly lower than the 85 kJ mol(-1) required for 30% aqueous MEA.
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