Paul E. Reyes‐Gutiérrez

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

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Filip Teplý

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

DŠ

David Šaman

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Ivana Cı́sařová

Charles University

Radek Pohl

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Lukáš Severa

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Václav Kašička

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Dušan Koval

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Petra Sázelová

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Miroslav Hájek

Czech University of Life Sciences Prague

Petr Slavı́ček

University of Chemistry and Technology, Prague

Cooperative Institutions

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Czech Academy of Sciences

Charles University

General University Hospital in Prague

University of Cambridge

University of Chemistry and Technology, Prague

Universidad Nacional Autónoma de México

Masaryk University

Central European Institute of Technology

Central European Institute of Technology – Masaryk University

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Functional helquats: helical cationic dyes with marked, switchable chiroptical properties in the visible region

Chemical Communications (2014)

Paul E. Reyes‐Gutiérrez Michael Jirásek Lukáš Severa Pavlína Novotná Dušan Koval

Helically chiral styryl dyes with large ECD in the visible region are introduced.

Helicene

Cationic polymerization

Chromophore

Visible spectrum

10.1039/c4cc08967g

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Citations (50)

Sulfonated Hydroxyaryl‐Tetrazines with Increased pKa for Accelerated Bioorthogonal Click‐to‐Release Reactions in Cells

Angewandte Chemie International Edition (2024)

Michal Rahm Patrick Keppel Rastislav Dzijak Martin Dračínský Veronika Šlachtová

Bioorthogonal reactions that enable switching molecular functions by breaking chemical bonds have gained prominence, with the tetrazine‐mediated cleavage of trans‐cyclooctene caged compounds (click‐to‐release) being particularly noteworthy for its high versatility, biocompatibility, and fast reaction rates. Despite several recent advances, the development of highly reactive tetrazines enabling quantitative elimination from trans‐cyclooctene linkers remains challenging. In this study, we present the synthesis and application of sulfo‐tetrazines, a class of derivatives featuring phenolic hydroxyl groups with increased acidity constants (pKa). This unique property leads to accelerated elimination and complete release of the caged molecules within minutes. Moreover, the inclusion of sulfonate groups provides a valuable synthetic handle, enabling further derivatization into sulfonamides, modified with diverse substituents. Significantly, we demonstrate the utility of sulfo‐tetrazines in efficiently activating fluorogenic compounds and prodrugs in living cells, offering exciting prospects for their application in bioorthogonal chemistry.

Bioorthogonal Chemistry

Tetrazine

Biocompatibility

Bioconjugation

Functional group

Cyclooctene

10.1002/anie.202411713

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Citations (1)

CCDC 1447598: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Harish R. Talele Dušan Koval Lukáš Severa Paul E. Reyes‐Gutiérrez Ivana Cı́sařová

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1klbq6

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Interactions of helquats with chiral acidic aromatic analytes investigated by partial-filling affinity capillary electrophoresis

Journal of Chromatography A (2016)

Martin Růžička Dušan Koval Jan Vávra Paul E. Reyes‐Gutiérrez Filip Teplý

Chiral ligand

10.1016/j.chroma.2016.08.053

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Citations (26)

CCDC 925830: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Paul E. Reyes‐Gutiérrez Michael Jirásek Lukáš Severa Pavlína Novotná Dušan Koval

Crystal (programming language)

10.5517/cc102dhz

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CCDC 1447596: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Harish R. Talele Dušan Koval Lukáš Severa Paul E. Reyes‐Gutiérrez Ivana Cı́sařová

10.5517/ccdc.csd.cc1klbn4

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CCDC 1413176: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Paul E. Reyes‐Gutiérrez Tynchtyk Amatov Pavel Švec Ivana Cı́sařová David Šaman

10.5517/ccdc.csd.cc1jfjbt

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Helquat dyes targeting G-quadruplexes as a new class of anti-HIV-1 inhibitors

Scientific Reports (2023)

Marcela Pávová Paul E. Reyes‐Gutiérrez Jaroslav Kozák Juraj Dobiáš Yevgen P. Yurenko

Abstract The secondary structure of nucleic acids containing quartets of guanines, termed G-quadruplexes, is known to regulate the transcription of many genes. Several G-quadruplexes can be formed in the HIV-1 long terminal repeat promoter region and their stabilization results in the inhibition of HIV-1 replication. Here, we identified helquat-based compounds as a new class of anti-HIV-1 inhibitors that inhibit HIV-1 replication at the stage of reverse transcription and provirus expression. Using Taq polymerase stop and FRET melting assays, we have demonstrated their ability to stabilize G-quadruplexes in the HIV-1 long-terminal repeat sequence. Moreover, these compounds were not binding to the general G-rich region, but rather to G-quadruplex-forming regions. Finally, docking and molecular dynamics calculations indicate that the structure of the helquat core greatly affects the binding mode to the individual G-quadruplexes. Our findings can provide useful information for the further rational design of inhibitors targeting G-quadruplexes in HIV-1.

G-quadruplex

Provirus

Transcription

10.1038/s41598-023-33263-3

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Citations (1)

HeliDye1: helquat fluorogenic probe specific for AT-rich DNA duplexes

Research Square (Research Square) (2022)

Erika Kužmová Vishwas N. Joshi Jaroslav Kozák Lukáš Severa Lucie Bednarova

Abstract DNA-binding fluorescent probes are useful tools in cell biology for various applications enabling visualisation and quantification of DNA. Herein, we report on HeliDye1 , a novel cationic helicene-like DNA probe, and its versatile usability. HeliDye1 exhibits fluorescence exclusively in the presence of DNA duplexes containing AT base pairs and (contrary to any recent DNA probe) it remains non-fluorescent in the presence of single-stranded DNA and RNA. Favourable chemical properties of HeliDye1 allowed its use in super-resolution microscopy and DNA quantification using flow cytometry. We present five more applications of HeliDye1 . Viscosimetry showed that HeliDye1 is a minor groove binder. HeliDye1 interacts with double-stranded DNA as an induced (P) -enantiomer, which we confirmed by ECD spectroscopy and DFT calculations. ECD spectroscopy suggested the formation of HeliDye1 dimers. MD simulations predicted the structures of (P) -HeliDye1 dimers inside DNA and showed their stability in AT-rich sequences and instability in GC-rich sequences.

10.21203/rs.3.rs-737372/v1

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Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Chemistry - A European Journal (2018)

Harish R. Talele Dušan Koval Lukáš Severa Paul E. Reyes‐Gutiérrez Ivana Cı́sařová

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol-1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.

Racemization

Chirality

Diquat

10.1002/chem.201800369

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Citations (8)