A Journey through 12 Years of Interacting Molecules: From Artificial Amino Acid Receptors to the Recognition of Biomolecules and Switchable [nl]Nanomaterials

Schmuck, Carsten

doi:10.1055/s-0030-1260946

Cited by 21 publications

(10 citation statements)

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“…At variance to all previously studied aryl-GCP conjugates [ 10 , 11 , 12 , 13 , 14 , 15 ] and even the Cy-GCP [ 17 ] (very close analog of 2 ), no ICD bands of GCP chromophore (at λ = 300 nm) were observed, pointing out that for both, 1 and 2 , GCP moiety was not uniformly oriented in respect to the polynucleotide chiral axis [ 32 ], similar as previously noted for nucleobase-GCP analogs [ 33 ].…”

Section: Resultsmentioning

confidence: 97%

“…The 2 was prepared as shown on Scheme 2 , starting from the corresponding cyanine-amino acids ( Cy-aa ) [ 19 ] and guanidiniocarbonyl-pyrrole ( GCP ) [ 10 , 11 , 12 ], following a similar procedure used previously for the preparation of its analog 1 [ 18 ]. Namely, the reaction mixture of Cy-amino acid and GCP in acetonitrile with O-(1H-6-Chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU) and Et 3 N was left stirring at room temperature under argon for three days.…”

Section: Resultsmentioning

confidence: 99%

“…Cyanine analogs are likely the most extensively used family of fluorogenic dyes, their particular advantage being non-emissive in free solution but strong emission fluorescence upon binding to the target [ 7 , 8 , 9 ]. On the other hand, our systematic work on aryl-guanidiniocarbonyl-pyrrole (GCP) derivatives characterized GCP moiety as a very useful building block in the design of new small molecules targeting DNA/RNA, particularly when conjugated with large aromatic fluorophores [ 10 , 11 , 12 ]. For instance, pyrene-GCP analogs have been shown to be very efficient single-molecule- multipurpose probes, being able to recognize between various ds-DNA and ds-RNA by simultaneous specific responses in fluorescence and circular dichroism [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate

et al. 2020

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Two novel isosteric conjugates of guanidiniocarbonyl-pyrrole and 6-bromo-TO (thiazole orange) were prepared, differing only in linker connectivity to cyanine (benzothiazole nitrogen vs. quinoline nitrogen). The quinoline analog was significantly more susceptible to aggregation in an aqueous medium, which resulted in induced circular dichroism (ICD; λ = 450–550 nm) recognition between A-T(U) and G-C basepair containing polynucleotides. The benzothiazole-isostere showed pronounced (four-fold) fluorimetric selectivity toward ds-RNA in comparison to any ds-DNA, at variance to its quinoline-analogue fluorescence being weakly selective to GC-DNA. Preliminary screening on human tumor and normal lung cell lines showed that both dyes very efficiently enter living cells and accumulate in mitochondria, causing moderate cytotoxic effects, and thus could be considered as lead compounds toward novel theragnostic mitochondrial dyes.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate

et al. 2020

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“…The interest is stimulated by its potential applications in diverse fields such as drug delivery, nutritional analysis and disease diagnosis. Various examples of the use of artificial receptors for amino acid (or peptide/protein) recognition have been reported 6 7 8 9 10 11 12 . Cucurbit[ n ]urils ( n = 5–8, 10, abbreviated as Q[ n ], Fig.…”

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confidence: 99%

Host-guest complexation of cucurbit[8]uril with two enantiomers

Gao

Lin

Bai

et al. 2017

Sci Rep

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“…Alkoxycarbonyl pyrroles have been used in supramolecular chemistry for self-assembly and in molecular recognition. 11 Our dialkoxycarbonyl dipyrromethanes represent a unique set of regiochemically differentiated compounds containing the typical framework used in the studies of supramolecular recognition processes. The three dipyrromethanes show three distinct and different packings in their crystal structures.…”

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confidence: 99%

Synthesis of α,β′- and β,β′-Linked Dimethoxycarbonyldipyrromethanes by Rothemund-Type Condensation

Journot

Stœckli-Evans

Neier

2012

Synlett

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The Rothemund-type condensation of methoxycarbonylpyrrole with acetone produces mainly the α,β′-linked dipyrromethane, a building block for the synthesis of N-confused macrocycles. The influence of the reaction conditions on the regioselectivity of the process is reported. The X-ray structures of the α,α′-, α,β′-and β,β′-linked dipyrromethanes show an interesting discrimination of the structurally different types of hydrogen bonds.The three important classical transformations of pyrroles, the Mannich reaction, the Vilsmeier-Haak reaction and the Rothemund condensation leading to porphyrins are all electrophilic aromatic substitution reactions showing a high α regioselectivity. The isolation and characterization of the so-called N-confused porphyrins at the end of the last century were spectacular findings. They attracted the attention of the synthetic community to the feasibility of obtaining β-substituted pyrroles via electrophilic substitution reactions. The discovery of products obtained by reaction at the β-position is largely due to the development of efficient and sensitive analytical methods. In the past the existence of a competition between α and β reactivity has been largely ignored. The products of β-substitution have probably often been discarded as unwanted side products. The new findings due the more sensitive analytics show that the regioselectivity is in favor of the α-position, but minor amounts of the β products are also formed. Reversing the selectivity of these reactions towards β reactivity remains a challenge. To develop conditions for either obtaining selectively α-or β-substituted pyrroles is of synthetic importance. Active ingredients containing substituted pyrroles have been part of important drug molecules. The chemistry and the synthesis of tetrapyrrolic macrocycles have regained importance for applications in materials science and catalysis. Controlling the regioselectivity of the electrophilic aromatic substitution process is a central factor for the efficient synthesis of N-confused macrocycles. Good methods of synthesizing mono-(α,β′-linked) or bis-confused (β,β′-linked) dipyrromethane as building blocks are needed (Figure 1). 1 Only few syntheses of confused dipyrromethanes have been described so far. Confused dipyrromethanes or confused macrocycles have been generally isolated as minor side products only. 2 Three main strategies exist for the synthesis of N-confused dipyrromethanes: 1) selective syntheses via multiple steps starting from a reactive species in the β-position of the pyrrole precursor; 3 2) avoiding the α-substitution by using an α,α′-substituted pyrrole as starting material 1h,4 or by introducing a bulky protecting group on the nitrogen; 1c,5 3) introducing an electron-withdrawing group on the pyrrole in order to change its electronic properties. 6 These strategies involve multiple steps and usually lead to the product in poor yields. To the best of our knowledge syntheses of Nconfused dipyrromethane starting from an α-free pyrrole in a single step have not been re...

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A Journey through 12 Years of Interacting Molecules: From Artificial Amino Acid Receptors to the Recognition of Biomolecules and Switchable [nl]Nanomaterials

Cited by 21 publications

References 46 publications

Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate

Fluorimetric and CD Recognition between Various ds-DNA/RNA Depends on a Cyanine Connectivity in Cyanine-guanidiniocarbonyl-pyrrole Conjugate

Host-guest complexation of cucurbit[8]uril with two enantiomers

Synthesis of α,β′- and β,β′-Linked Dimethoxycarbonyldipyrromethanes by Rothemund-Type Condensation

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