Selective Extraction of G‐Quadruplex Ligands from a Rationally Designed Scaffold‐Based Dynamic Combinatorial Library

Nielsen, Mads C.; Ulven, Trond

doi:10.1002/chem.200801109

Cited by 16 publications

(13 citation statements)

References 55 publications

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“…The clear trend towards higher melting temperatures for the guanidinium ligands thus indicates that the off-rates of the ligands have higher influence on thermal stability than the on-rates. A preferred role of the guanidinium group in quadruplex ligands is supported by two independent dynamic combinatorial libraries targeting quadruplex DNA, which both identified the guanidinium-containing compounds as the favored library members, 43,44 and by the higher efficiency of the guanidinium-containing steroid FG exhibited compared to the analogous trimethylammonium steroid maouetine. 45 …”

Section: Resultsmentioning

confidence: 98%

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Nielsen

Borch

Ulven

2009

Bioorganic & Medicinal Chemistry

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Section: Resultsmentioning

confidence: 98%

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Nielsen

Borch

Ulven

2009

Bioorganic & Medicinal Chemistry

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“…The ligands LSSL and L Me SSL Me were synthesized by using a combination of reported procedures (see the Supporting Information, Scheme S1). [18][19][20] 2 were obtained by vapor diffusion of pentane into this acetone solution; its structure was confirmed by single crystal X-ray crystallography. Projections of the cationic parts of the two structures are depicted in Figure 1.…”

Section: Introductionmentioning

confidence: 91%

“…Ligand and complex synthesis LSSL: This ligand was synthesized using a combination of reported syntheses. [18][19][20] Di-(2-picolyl)amine (2.0 mL, 11.0 mmol) was dissolved in CH 3 CN (10 mL) under argon. Propylene sulfide (1.3 mL, 16.5 mmol) was added, after which the reaction mixture was stirred for 15 h at 70 8C under argon.…”

Section: Dft Calculationsmentioning

confidence: 99%

Protonation of a Biologically Relevant Cu^II μ‐Thiolate Complex: Ligand Dissociation or Formation of a Protonated Cu^I Disulfide Species?

Ording-Wenker

Plas

Siegler

et al. 2014

Chemistry A European J

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The proton-induced electron-transfer reaction of a Cu(II) μ-thiolate complex to a Cu(I) -containing species has been investigated, both experimentally and computationally. The Cu(II) μ-thiolate complex [Cu(II) 2 (L(Me) S)2 ](2+) is isolated with the new pyridyl-containing ligand L(Me) SSL(Me) , which can form both Cu(II) thiolate and Cu(I) disulfide complexes, depending on the solvent. Both the Cu(II) and the Cu(I) complexes show reactivity upon addition of protons. The multivalent tetranuclear complex [Cu(I) 2 Cu(II) 2 (LS)2 (CH3 CN)6 ](4+) crystallizes after addition of two equivalents of strong acid to a solution containing the μ-thiolate complex [Cu(II) 2 (LS)2 ](2+) and is further analyzed in solution. This study shows that, upon addition of protons to the Cu(II) thiolate compound, the ligand dissociates from the copper centers, in contrast to an earlier report describing redox isomerization to a Cu(I) disulfide species that is protonated at the pyridyl moieties. Computational studies of the protonated Cu(II) μ-thiolate and Cu(I) disulfide species with LSSL show that already upon addition of two equivalents of protons, ligand dissociation forming [Cu(I) (CH3 CN)4 ](+) and protonated ligand is energetically favored over conversion to a protonated Cu(I) disulfide complex.

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“…7). [40] Three aromatic scaffolds, each carrying positively charged side-chains, were designed based on the structures of the majority of G-quadruplex ligands, which generally contain a central aromatic scaffold with one or several positively charged side chains. Cystamine hydrochloride was used to initiate the reaction, and the DCL was generated from the scaffolds and a large excess of the positively charged side chains in order to minimize oligomerization of the scaffolds.…”

Section: Quadruplex Dnamentioning

confidence: 99%

Targeting Nucleic Acids using Dynamic Combinatorial Chemistry

Durai

Harding

2011

Aust. J. Chem.

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Dynamic combinatorial chemistry (DCC) is a powerful method for the identification of novel ligands for the molecular recognition of receptor molecules. The method relies on self-assembly processes to generate libraries of compounds under reversible conditions, allowing a receptor molecule to select the optimal binding ligand from the mixture. However, while DCC is now an established field of chemistry, there are limited examples of the application of DCC to nucleic acids. The requirement to conduct experiments under physiologically relevant conditions, and avoid reaction with, or denaturation of, the target nucleic acid secondary structure, limits the choice of the reversible chemistry, and presents restrictions on the building block design. This review will summarize recent examples of applications of DCC to the recognition of nucleic acids. Studies with duplex DNA, quadruplex DNA, and RNA have utilized mainly thiol disulfide libraries, although applications of imine libraries, in combination with metal coordination, have been reported. The use of thiol disulfide libraries produces lead compounds with limited biostability, and hence design of stable analogues or mimics is required for many applications.

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Selective Extraction of G‐Quadruplex Ligands from a Rationally Designed Scaffold‐Based Dynamic Combinatorial Library

Cited by 16 publications

References 55 publications

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Protonation of a Biologically Relevant Cu^II μ‐Thiolate Complex: Ligand Dissociation or Formation of a Protonated Cu^I Disulfide Species?

Targeting Nucleic Acids using Dynamic Combinatorial Chemistry

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Selective Extraction of G‐Quadruplex Ligands from a Rationally Designed Scaffold‐Based Dynamic Combinatorial Library

Cited by 16 publications

References 55 publications

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Design, synthesis and evaluation of 4,7-diamino-1,10-phenanthroline G-quadruplex ligands

Protonation of a Biologically Relevant CuII μ‐Thiolate Complex: Ligand Dissociation or Formation of a Protonated CuI Disulfide Species?

Targeting Nucleic Acids using Dynamic Combinatorial Chemistry

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Protonation of a Biologically Relevant Cu^II μ‐Thiolate Complex: Ligand Dissociation or Formation of a Protonated Cu^I Disulfide Species?