Photoinduced Release of DNA‐Binding Ligands from the [4+4] Dimers of Benzo[<i>b</i>]quinolizinium and Anthracene Derivatives

Berdnikova, Daria V.; Heider, Josef; Ihmels, Heiko; Sewald, Norbert; Pithan, Phil M.

doi:10.1002/cptc.202000015

Cited by 7 publications

(3 citation statements)

References 97 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Detailed investigation of these bio‐macromolecules and understanding of the interactions that influence their communication on a molecular level is a broad and interdisciplinary research field. One well‐established way to approach the subject is to study the interactions and binding behaviours of small molecules with DNA and RNA [6–17] …”

Section: Introductionmentioning

confidence: 99%

“…One well-established way to approach the subjecti st os tudy the interactions andb inding behaviours of small molecules with DNA and RNA. [6][7][8][9][10][11][12][13][14][15][16][17] There are three main binding modes, namely intercalation, groove binding and external binding (Figure 1). [22,23] For intercalation to occur,t he helical structureo ft he bio-macromole-cule needs to unwind to allow for as mall molecule to insert in between the coplanarly arranged nucleobases.…”

Section: Introductionmentioning

confidence: 99%

“…Figure16. The results of 90 (left), 95 (middle) and 300 ns (right) of moleculardynamics simulation of the 5/DNA complex with the dimer of 5 bound initially into the major groove.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Ferger

Ban

Krošl

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

We report four new luminescent tetracationic bis‐triarylborane DNA and RNA sensors that show high binding affinities, in several cases even in the nanomolar range. Three of the compounds contain substituted, highly emissive and structurally flexible bis(2,6‐dimethylphenyl‐4‐ethynyl)arene linkers (3: arene=5,5′‐2,2′‐bithiophene; 4: arene=1,4‐benzene; 5: arene=9,10‐anthracene) between the two boryl moieties and serve as efficient dual Raman and fluorescence chromophores. The shorter analogue 6 employs 9,10‐anthracene as the linker and demonstrates the importance of an adequate linker length with a certain level of flexibility by exhibiting generally lower binding affinities than 3–5. Pronounced aggregation–deaggregation processes are observed in fluorimetric titration experiments with DNA for compounds 3 and 5. Molecular modelling of complexes of 5 with AT‐DNA, suggest the minor groove as the dominant binding site for monomeric 5, but demonstrate that dimers of 5 can also be accommodated. Strong SERS responses for 3–5 versus a very weak response for 6, particularly the strong signals from anthracene itself observed for 5 but not for 6, demonstrate the importance of triple bonds for strong Raman activity in molecules of this compound class. The energy of the characteristic stretching vibration of the C≡C bonds is significantly dependent on the aromatic moiety between the triple bonds. The insertion of aromatic moieties between two C≡C bonds thus offers an alternative design for dual Raman and fluorescence chromophores, applicable in multiplex biological Raman imaging.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Ferger

Ban

Krošl

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Schlosser,

Stötzel,

Fedorov

et al. 2023

ChemPhotoChem

Self Cite

View full text Add to dashboard Cite

The photocyclization reaction of sterically demanding styrylpyridine derivatives was investigated and shown to depend on the type of substituent. With this method, a 2,2‐diphenyl‐1,3‐benzodioxolo‐annelated benzo[c]quinolizinium was synthesized, and its association with regular and abasic site‐containing DNA (AP‐DNA) was investigated by absorption, fluorescence, circular and linear dichroism spectroscopy. Specifically, this ligand binds preferentially to AP‐DNA relative to regular duplex DNA, and the AP‐DNA/ligand complex is formed in situ upon irradiation of the styrylpyridine substrate in the presence of the DNA.

show abstract

Photoinduced [2+2] and [4+4] Cycloaddition and Cycloreversion Reactions for the Development of Photocontrollable DNA Binders

Dohmen,

Ihmels

2024

ChemPhotoChem

View full text Add to dashboard Cite

In the current field of photopharmacology, molecular photoswitches are applied whose interactions with DNA can be triggered or controlled by light. And although several photochromic reactions have been shown to serve this purpose well, the reversible photocycloaddition and photocycloreversion reactions have been largely neglected. This absence of research is surprising because especially the photodimerization of a DNA ligand leads to products with significant change of the size and shape which, in turn, leads to strongly diminished or even suppressed DNA association. Therefore, photocycloaddition‐cycloreversion sequences have a huge potential for the photoinduced, reversible deactivation and activation of ligand‐DNA interactions, as will be shown with selected examples in this Concept. Specifically, heterostyryl and ‐stilbene derivatives are presented whose DNA‐binding properties are efficiently switched in reversible [2+2] photocycloaddition reactions. In addition, the photocontrolled DNA‐binding of anthracene derivatives and their heterocyclic benzo[b]quinolizinium analogues in a [4+4] photocycloaddition, as well as the use of this reaction as part of dual‐mode switches in combination with redox‐active functionalities, are highlighted. Furthermore, examples of conjugates are provided, in which the photochromic unit is bound covalently to nucleic acids or proteins, such that the photocycloaddition reaction can be used for reversible photoinduced crosslinking, ligation, or inhibition of gene expression.

show abstract

Photoinduced Release of DNA‐Binding Ligands from the [4+4] Dimers of Benzo[b]quinolizinium and Anthracene Derivatives

Cited by 7 publications

References 97 publications

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Photoinduced [2+2] and [4+4] Cycloaddition and Cycloreversion Reactions for the Development of Photocontrollable DNA Binders

Contact Info

Product

Resources

About