Selective covalent binding of a positively charged water-soluble benzoheterocycle triosmium cluster to single- and double-stranded DNA

Using coarse-grained dissipative particle dynamics (DPD) with explicit electrostatics, we performed (i) an extensive series of simulations of the electrostatic co-assembly of asymmetric oppositely charged copolymers composed of one (either positively or negatively charged) polyelectrolyte (PE) block A and one water-soluble block B and (ii) studied the solubilization of positively charged porphyrin derivatives (P+) in the interpolyelectrolyte complex (IPEC) cores of co-assembled nanoparticles. We studied the stoichiometric mixtures of 137 A10+B25 and 137 A10−B25 chains with moderately hydrophobic A blocks (DPD interaction parameter aAS=35) and hydrophilic B blocks (aBS=25) with 10 to 120 P+ added (aPS=39). The P+ interactions with other components were set to match literature information on their limited solubility and aggregation behavior. The study shows that the moderately soluble P+ molecules easily solubilize in IPEC cores, where they partly replace PE+ and electrostatically crosslink PE− blocks. As the large P+ rings are apt to aggregate, P+ molecules aggregate in IPEC cores. The aggregation, which starts at very low loadings, is promoted by increasing the number of P+ in the mixture. The positively charged copolymers repelled from the central part of IPEC core partially concentrate at the core-shell interface and partially escape into bulk solvent depending on the amount of P+ in the mixture and on their association number, AS. If AS is lower than the ensemble average ⟨AS⟩n, the copolymer chains released from IPEC preferentially concentrate at the core-shell interface, thus increasing AS, which approaches ⟨AS⟩n. If AS>⟨AS⟩n, they escape into the bulk solvent.

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Water-Soluble Conjugate of Double-Stranded DNA and Poly(N-isopropylacrylamide) for One-Pot Affinity Precipitation Separation of DNA-Binding Proteins

Bioconjugate Chemistry ◽

10.1021/bc980019f ◽

1998 ◽

Vol 9 (6) ◽

pp. 719-724 ◽

Cited By ~ 41

Author(s):

Daisuke Umeno ◽

Masafumi Kawasaki ◽

Mizuo Maeda

Keyword(s):

Dna Binding ◽

Binding Proteins ◽

Dna Binding Proteins ◽

Water Soluble ◽

One Pot ◽

Affinity Precipitation ◽

Double Stranded Dna

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Interactions of a biocompatible water-soluble anthracenyl polymer derivative with double-stranded DNA

Physical Chemistry Chemical Physics ◽

10.1039/c5cp05381a ◽

2015 ◽

Vol 17 (45) ◽

pp. 30318-30327 ◽

Cited By ~ 18

Author(s):

Marco Deiana ◽

Bastien Mettra ◽

Katarzyna Matczyszyn ◽

Katarzyna Piela ◽

Delphine Pitrat ◽

...

Keyword(s):

Water Soluble ◽

Double Stranded Dna

We have studied the interaction of a polymeric water soluble anthracenyl derivative (Ant-PHEA) with salmon testes DNA.

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Synthesis, Characterization, and Interaction with Biomolecules of Platinum(II) Complexes with Shikimic Acid-Based Ligands

Bioinorganic Chemistry and Applications ◽

10.1155/2013/565032 ◽

2013 ◽

Vol 2013 ◽

pp. 1-12 ◽

Cited By ~ 4

Author(s):

Yan Peng ◽

Min-Min Zhang ◽

Zhen-Feng Chen ◽

Kun Hu ◽

Yan-Cheng Liu ◽

...

Keyword(s):

Shikimic Acid ◽

Covalent Binding ◽

Carbon Chain ◽

Water Soluble ◽

Cytotoxic Activities ◽

Experimental Conditions ◽

H Nmr ◽

Mtt Method ◽

Low Cytotoxicity

Starting from the active ingredient shikimic acid (SA) of traditional Chinese medicine and NH2(CH2)nOH, (n=2–6), we have synthesized a series of new water-soluble Pt(II) complexes PtLa–eCl2, where La–eare chelating diamine ligands with carbon chain covalently attached to SA (La–e= SA-NH(CH2)nNHCH2CH2NH2; La,n=2; Lb,n=3; Lc,n=4; Ld,n=5; Le,n=6). The results of the elemental analysis, LC-MS, capillary electrophoresis, and1H,13C NMR indicated that there was only one product (isomer) formed under the present experimental conditions, in which the coordinate mode of PtLa–eCl2was two-amine bidentate. Theirin vitrocytotoxic activities were evaluated by MTT method, where these compounds only exhibited low cytotoxicity towards BEL7404, which should correlate their low lipophilicity. The interactions of the five Pt(II) complexes with DNA were investigated by agarose gel electrophoresis, which suggests that the Pt(II) complexes could induce DNA alteration. We also studied the interactions of the Pt(II) complexes with5′-GMP with ESI-MS and1H NMR and found that PtLbCl2, PtLcCl2, and PtLdCl2could react with5′-GMP to form mono-GMP and bis-GMP adducts. Furthermore, the cell-cycle analysis revealed that PtLbCl2, PtLcCl2cause cell G2-phase arrest after incubation for 72 h. Overall, these water-soluble Pt(II) complexes interact with DNA mainly through covalent binding, which blocks the DNA synthesis and replication and thus induces cytotoxicity that weakens as the length of carbon chain increases.

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Sensing of Double-Stranded DNA/RNA Secondary Structures by Water Soluble Homochiral Perylene Bisimide Dyes

Chemistry - A European Journal ◽

10.1002/chem.201500184 ◽

2015 ◽

Vol 21 (21) ◽

pp. 7886-7895 ◽

Cited By ~ 22

Author(s):

Jana Gershberg ◽

Marijana Radić Stojković ◽

Marko Škugor ◽

Sanja Tomić ◽

Thomas H. Rehm ◽

...

Keyword(s):

Secondary Structures ◽

Water Soluble ◽

Rna Secondary Structures ◽

Perylene Bisimide ◽

Double Stranded Dna

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Binding of two spin-labelled derivatives of chlorpromazine to human erythrocytes

Biochemical Journal ◽

10.1042/bj2640633 ◽

1989 ◽

Vol 264 (3) ◽

pp. 633-641 ◽

Cited By ~ 4

Author(s):

J L Olivier ◽

C Chachaty ◽

C Wolf ◽

D Daveloose ◽

G Bereziat

Keyword(s):

Spin Label ◽

Binding Sites ◽

Spin Probe ◽

Slow Motion ◽

Water Soluble ◽

Spin Labels ◽

Exponential Dependence ◽

Exchange Frequency ◽

Derivatives Of ◽

Positively Charged

The binding to human intact erythrocytes of two different spin-labelled derivatives of chlorpromazine has been studied. The influence of the positively charged side chain of the drug has been the focus of our attention. The positively charged amphiphilic compound (spin derivative I) is water-soluble up to 80 microM at pH values below 5.9. The apolar analogue (spin derivative II) aggregates in aqueous buffer from the lowest concentration tested. Both spin derivatives undergo a slow reduction inside the erythrocyte. The reduced nitroxides are readily reoxidized by adding a low, non-quenching, concentration of potassium ferricyanide to the intact erythrocytes. The fractions of spin label I and II bound to the erythrocyte membrane or to the erythrocyte-extracted lipids remain constant as a function of the temperature (3-42 degrees C) and as a function of the concentration of the spin label up to 150 microM. E.s.r. spectra of both spin labels show a two-component lineshape when they are bound to intact erythrocytes. Below 35 degrees C for the positively charged spin probe, and below 32 degrees C for the apolar spin probe, the simulation of the lineshape shows that more than 50% of the spectrum originates from a slow-motion component. This slow-motion component is also found in erythrocyte-extracted lipids probed by the positively charged spin label below 25 degrees C. In contrast, no slow-motion component is detected in the range 4-40 degrees C for the apolar spin label in erythrocyte-extracted lipids. In this environment the apolar probe experiences a single fast anisotropic motion with an exponential dependence on 1/temperature. Detailed lineshape simulations take into account the exchange frequency between binding sites where the probe experiences a fast motion and binding sites where it experiences a slow motion. The exchange frequency is strongly temperature-dependent. Characterization of the different motions experienced inside the different locations has been achieved and compared for whole erythrocytes and for the extracted lipids. The biochemical nature of the binding sites (membrane protein/acidic phospholipid) giving rise to the slow-motion component is discussed as a function of the polarity of the spin-labelled drug and as a function of the temperature controlling the fluidity of the lipid bulk and influencing the distribution of the drug inside the membrane.

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Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

Beilstein Journal of Nanotechnology ◽

10.3762/bjnano.8.184 ◽

2017 ◽

Vol 8 ◽

pp. 1825-1835 ◽

Cited By ~ 4

Author(s):

Pavel L Padnya ◽

Irina A Khripunova ◽

Olga A Mostovaya ◽

Timur A Mukhametzyanov ◽

Vladimir G Evtugyn ◽

...

Keyword(s):

Electron Microscopy ◽

Self Assembly ◽

Water Soluble ◽

Fluorescent Nanoparticles ◽

Spectral Emission ◽

Chiroptical Properties ◽

Transmission Electron ◽

Derivatives Of ◽

Tryptophan Derivatives ◽

Positively Charged

New water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a concentration of 1 × 10−4 M as confirmed by dynamic light scattering, scanning electron microscopy and transmission electron microscopy. It was established that these aggregates are fluorescently active and chiral. A distinctive feature of the compounds is the pronounced dependence of their spectral (emission and chiroptical) properties on the polarity of the solvent and the length of the linker between the macrocyclic and fluorophore parts of the molecule.

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Porphyrins and Metalloporphyrins: Potential Hypoxic Agents

Metal-Based Drugs ◽

10.1155/mbd.1996.85 ◽

1996 ◽

Vol 3 (2) ◽

pp. 85-89 ◽

Cited By ~ 9

Author(s):

B. R. James ◽

G. G. Meng ◽

J. J. Posakony ◽

J. A. Ravensbergen ◽

C. J. Ware ◽

...

Keyword(s):

Copper Complex ◽

Chinese Hamster Ovary ◽

Chinese Hamster ◽

Cobalt Complexes ◽

Water Soluble ◽

The Other ◽

Enhancement Ratio ◽

Selective Toxicity ◽

Further Development ◽

Positively Charged

Synthetic water-soluble porphyrins and their metalloporphyrin derivatives with Co(III), Cu(II), Ru(II) and Pt(II), containing various functional groups within the meso-positions of the porphyrin, were synthesised and evaluated as hypoxic agents, especially as cytotoxins and radiosensitisers. Cobalt complexes of the porphyrins containing positively charged methylpyridinium groups showed selective toxicity toward hypoxic Chinese Hamster Ovary (CHO) cells. The Co(III) complexes of the cationic and the anionic porphyrins are all weak radiosensitisers toward hypoxic cells, the highest sensitisation enhancement ratio (SER = 1.22, at 50 μM) being with a porphyrin complex containing a cis-arrangement of two nitro and two methylpyridinium meso-substituents. A copper complex of a tetracationic porphyrin showed slight radiosensitisation activity with an SER value of about 1.1. The other metalloporphyrins showed no hypoxic selectivity or radiosensitisation activity. In total, over 50 porphyrin free bases have been synthesised, of which half are water-soluble and have been metallated; thus, the chemistry is now in place for further development of water-soluble hypoxic agents.

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