Tomas Fiala

ORCID: 0000-0001-6949-4561
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About
Contact & Profiles
Research Areas
  • Photochromic and Fluorescence Chemistry
  • Collagen: Extraction and Characterization
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Conducting polymers and applications
  • Protein Hydrolysis and Bioactive Peptides
  • Chemical synthesis and alkaloids
  • Traditional and Medicinal Uses of Annonaceae
  • Alkaloids: synthesis and pharmacology
  • Marine Biology and Environmental Chemistry
  • Neuroscience and Neural Engineering
  • Receptor Mechanisms and Signaling
  • Neuroscience and Neuropharmacology Research
  • Neuroinflammation and Neurodegeneration Mechanisms
  • Photoacoustic and Ultrasonic Imaging
  • Bamboo properties and applications
  • Enzyme Production and Characterization
  • Advanced Fluorescence Microscopy Techniques
  • Carbon dioxide utilization in catalysis
  • Crystallography and molecular interactions
  • Proteins in Food Systems
  • bioluminescence and chemiluminescence research
  • Photochemistry and Electron Transfer Studies
  • Oxidative Organic Chemistry Reactions
  • Polymer Surface Interaction Studies

Masaryk University
2013-2025

Columbia University
2018-2024

ETH Zurich
2021-2024

RECETOX
2013

The serotonergic transmitter system plays fundamental roles in the nervous neurotransmission, synaptic plasticity, pathological processes, and therapeutic effects of antidepressants psychedelics, as well gastrointestinal circulatory systems. We introduce a novel small molecule fluorescent agent, termed SERTlight, that specifically labels neuronal cell bodies, dendrites, axonal projections serotonin transporter (SERT) substrate. SERTlight was developed by an iterative molecular design...

10.1021/jacs.3c11617 article EN Journal of the American Chemical Society 2024-04-01

Driving forces of anion binding in water contrast to nonpolar environments are high interest because their relevance biology and medicine. Here we report a neutral bambusuril macrocycle (1), soluble both solvents due decoration with 12 polyethylene glycol-based substituents. The new has the highest affinity for I– pure ever reported synthetic relying on hydrogen bonding interactions rather than metal coordination or Coulombic forces. Isothermal titration calorimetry (ITC) experiments nine...

10.1021/acs.joc.7b02846 article EN The Journal of Organic Chemistry 2018-01-26

Methyl viologen hexafluorophosphate (MV2+·2PF6–) and dodecamethylbambus[6]uril (BU6) form crystals in which the layers of dications alternate with those a 1:2 supramolecular complex BU6 PF6–. This arrangement allows for one-electron reduction MV2+ ions upon UV irradiation to MV+• radical cations within crystal structure half-lives several hours air. The mechanism this photoinduced electron transfer solid state origin long-lived charge-separated were studied by steady-state transient...

10.1021/jacs.6b08589 article EN Journal of the American Chemical Society 2017-02-13

Mitragynine (MG) is the most abundant alkaloid component of psychoactive plant material "kratom", which according to numerous anecdotal reports shows efficacy in self-medication for pain syndromes, depression, anxiety, and substance use disorders. We have developed a synthetic method selective functionalization unexplored C11 position MG scaffold (C6 indole numbering) via an indole-ethylene glycol adduct subsequent iridium-catalyzed borylation. Through this work we discover that represents...

10.1038/s41467-021-23736-2 article EN cc-by Nature Communications 2021-06-22

Collagen model peptides (CMPs), composed of proline–(2S,4R)-hydroxyproline–glycine (POG) repeat units, have been extensively used to study the structure and stability triple-helical collagen─the dominant structural protein in mammals─at molecular level. Despite more than 50-year history CMPs numerous studies on relationship between composition single-stranded thermal assembled triple helices, little attention has paid effects arising from their terminal residues. Here, we show that...

10.1021/jacs.2c08727 article EN Journal of the American Chemical Society 2022-09-30

Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. The impact of these highly lipophilic sensors has, however, been limited due to the lack cell-specific targeting methods brain tissue or living animals. We address this key challenge by introducing a nongenetic molecular platform cell- molecule-specific synthetic VSDs brain. employ dextran polymer particle overcome inherent lipophilicity dynamic encapsulation...

10.1021/jacs.0c00861 article EN Journal of the American Chemical Society 2020-05-12

N-terminal acylation is a common tool for the installation of functional moieties (e.g., sensors or bioactive molecules) on collagen model peptides (CMPs). The N-acyl group and its length are generally assumed to have little no influence properties triple helix formed by CMP. Here, we show that short (C1–C4) acyl capping groups has different effects thermal stability helices in POG, OGP, GPO frames. While effect frame negligible, longer chains stabilize OGP but destabilize POG analogues....

10.1021/acs.biomac.3c00241 article EN Biomacromolecules 2023-05-25

Abstract Collagen model peptides (CMPs) consisting of proline‐(2 S ,4 R )‐hydroxyproline‐glycine (POG) repeats have provided a breadth knowledge the triple helical structure collagen, most abundant protein in mammals. Predictive tools for helix stability have, however, lagged behind since effect CMPs with different frames ([POG] n , [OGP] or [GPO] ) and capped uncapped termini so far been underestimated. Here, we elucidated impact frame, terminal functional group its charge on collagen...

10.1002/anie.202214728 article EN Angewandte Chemie International Edition 2022-11-21

Nature uses elaborate methods to control protein assembly, including that of heterotrimeric collagen. Here, we established design principles for the composition and register-selective assembly synthetic collagen heterotrimers. The code enabled self-sorting eight different strands into three─out 512 possible─triple helices via complementary (4S)-aminoproline aspartate residues. Native ESI-MS corroborated specific coexisting

10.1021/jacs.3c12295 article EN Journal of the American Chemical Society 2023-12-29

Abstract1H NMR spectrometry and X-ray diffraction were used to investigate supramolecular complexes of bambusurils dialkyl phosphates. It was shown that bambusuril forms external 1:1 stoichiometry with phosphates in chloroform solution. Conversely, a 2:1 complex observed the solid state which each opposed macrocycle portals is occupied by one phosphate anion. Exclusive preference over inclusion binding organic precludes these be for preparation interlocked structures.Keywords: Host–guest...

10.1080/10610278.2016.1146278 article EN Supramolecular chemistry 2016-02-16

Ethyleneurea fused with a norbornane ring was prepared. Acid-catalyzed polycondensation of the urea paraformaldehyde yielded new six-membered hemicucurbituril derivative. The presence hemicucurbiturils containing from four to eight monomer units were also detected.

10.1055/s-0033-1339850 article EN Synlett 2013-09-13

Carbohydrates are common co-solutes for the stabilization of proteins. The effect carbohydrate solutions on stability collagen, most abundant protein in mammals, is, however, underexplored. In this work, we studied thermal collagen triple helices derived from a molecularly defined model peptide (CMP), Ac-(Pro-Hyp-Gly)

10.1002/cbic.202300860 article EN cc-by-nc-nd ChemBioChem 2024-01-18

<p>Mitragynine is the most abundant alkaloid component of psychoactive plant material “kratom”, which according to numerous anecdotal reports shows efficacy in self-medication for pain syndromes, depression, anxiety, and substance use disorders. We developed a new synthetic method selective functionalization unexplored C11 position mitragynine scaffold (C6 indole numbering) via an indole-ethylene glycol adduct subsequent iridium-catalyzed borylation. discovered that represents key...

10.26434/chemrxiv.12799787 preprint EN 2020-08-14

Abstract Collagen model peptides (CMPs) consisting of proline‐(2 S ,4 R )‐hydroxyproline‐glycine (POG) repeats have provided a breadth knowledge the triple helical structure collagen, most abundant protein in mammals. Predictive tools for helix stability have, however, lagged behind since effect CMPs with different frames ([POG] n , [OGP] or [GPO] ) and capped uncapped termini so far been underestimated. Here, we elucidated impact frame, terminal functional group its charge on collagen...

10.1002/ange.202214728 article EN cc-by-nc-nd Angewandte Chemie 2022-11-21

Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. These sensors, rendered highly lipophilic to anchor the conjugated pi-wire molecular framework membrane, offer several favorable functional parameters including fast response kinetics high sensitivity membrane potential changes. The impact of VSDs has, however, been limited due lack cell-specific targeting methods brain tissue or living animals. We address this...

10.26434/chemrxiv.6955355.v2 preprint EN 2020-01-22

Collagen, the most widespread protein in animals, contains glycine as every third amino acid. This regular repetition of residues is required for tight packing collagen triple helix. In this work, we substitute with its homolog β-alanine model peptides (CMPs) and study effect on formation helices. While middle CMP sequences incompatible helix formation, terminal are tolerated. The work highlights critical role collagen.

10.1016/j.tetlet.2024.154964 article EN cc-by Tetrahedron Letters 2024-02-20

Optical imaging of changes in the membrane potential living cells can be achieved by means fluorescent voltage-sensitive dyes (VSDs). A particularly challenging task is to efficiently deliver these highly lipophilic probes specific neuronal subpopulations brain tissue. We have tackled this designing a solubilizing, hydrophilic polymer platform that carries high-affinity ligand for protein marker interest and VSD. Here, we disclose an improved design polymer-supported chemical, nongenetic...

10.1021/acschemneuro.1c00862 article EN ACS Chemical Neuroscience 2022-04-10

Mitragynine is the most abundant alkaloid component of psychoactive plant material “kratom”, which according to numerous anecdotal reports shows efficacy in self-medication for pain syndromes, depression, anxiety, and substance use disorders. We developed a new synthetic method selective functionalization unexplored C11 position mitragynine scaffold (C6 indole numbering) via an indole-ethylene glycol adduct subsequent iridium-catalyzed borylation. discovered that represents key locant...

10.26434/chemrxiv.12799787.v1 preprint EN 2020-08-14

Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. These sensors, rendered highly lipophilic to anchor the conjugated p-wire molecular framework membrane, offer several favorable functional parameters including fast response kinetics high sensitivity membrane potential changes. The impact of VSDs has however been limited due lack cell-specific targeting methods brain tissue or living animals. We address this key...

10.26434/chemrxiv.6955355.v1 preprint EN cc-by-nc-nd 2018-08-13

Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. These sensors, rendered highly lipophilic to anchor the conjugated pi-wire molecular framework membrane, offer several favorable functional parameters including fast response kinetics high sensitivity membrane potential changes. The impact of VSDs has, however, been limited due lack cell-specific targeting methods brain tissue or living animals. We address this...

10.26434/chemrxiv.6955355 preprint EN cc-by-nc-nd 2018-08-13
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