IOCB covers 2020

Substituted ferrocene derivatives with tuned redox potentials were tested as redox labels for electrochemical detection and coding of nucleobases in DNA. The ferrocene-linked nucleotides were enzymatically incorporated to DNA and analyzed by using capture probes on gold electrodes. Ferrocenecarboxamide and ethynylferrocene were used as tags for orthogonal ratiometric coding and analysis of cytosine and adenine in DNA. (Covert art: Tomáš Belloň / IOCB Prague)

• Article: Simonova, A.; Magriñá, I.; Sýkorová, V.; Pohl, R.; Ortiz, M.; Havran, L.; Fojta, M.; O'Sullivan, C. K.; Hocek, M. Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA. Chem. Eur. J. 2020, 26, 1286–1291. https://doi.org/10.1002/chem.201904700
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Advanced molecular nanocarbons are now in the spotlight reflecting the basic discoveries of fullerenes, carbon nanotubes, and graphene. Iconic helicenes and their congeners combine a unique π-electron system with helical chirality that makes them highly attractive in various fields of science. (Covert art: Tomáš Belloň / IOCB Prague)

• Article: Stará, I. G.; Starý, I. Helically Chiral Aromatics: The Synthesis of Helicenes by [2 + 2 + 2] Cycloisomerization of π-Electron Systems. Acc. Chem. Res. 2020, 53, 144–158. https://doi.org/10.1021/acs.accounts.9b00364 
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Covert art: Tomáš Belloň / IOCB Prague

• Article: Strmeň, T.; Vrkoslav, V.; Bosáková, Z.; Cvačka, J. Atmospheric pressure chemical ionization mass spectrometry at low flow rates: Importance of ion source housing. Rapid Commun. Mass Sp. 2020, 34, e8722. https://doi.org/10.1002/rcm.8722
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Artistic abstraction of how ammonia solutions change with increasing excess electron concentration. Microjets of liquid ammonia can be used to track how an electrically insulating liquid becomes a metal, with an accompanying color change from transparent blue through deeper blue to bronze. Mapping energy levels spectroscopically and theoretically reveals a gradual transition from electrolyte to liquid metal. (Cover art: C. Bickel/Science)

• Article: Buttersack, T.; Mason, P. E.; McMullen, R. S.; Schewe, H. C.; Martinek, T.; Brezina, K.; Crhan, M.; Gomez, A.; Hein, D.; Wartner, G.; Seidel, R.; Ali, H.; Thürmer, S.; Marsalek, O.; Winter, B.; Bradforth, S. E.; Jungwirth, P. Photoelectron spectra of alkali metal–ammonia microjets: From blue electrolyte to bronze metal. Science 2020, 368, 1086–1091. https://doi.org/10.1126/science.aaz7607
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Using solid-state NMR spectroscopy, the cis/trans isomerization in a 2-D array of surface-mounted azobenzene-based switches was detected for the first time. In order to achieve this, a new class of rod-shaped molecular switches was synthesized. The switching of individual molecules is not compromised by the close proximity of neighbors. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Santos Hurtado, C.; Bastien, G.; Mašát, M.; Štoček, J. R.; Dračínský, M.; Rončević, I.; Císařová, I.; Rogers, C. T.; Kaleta, J. Regular Two-Dimensional Arrays of Surface-Mounted Molecular Switches: Switching Monitored by UV–vis and NMR Spectroscopy.  J. Am. Chem. Soc. 2020, 142, 9337–9351. https://doi.org/10.1021/jacs.0c01753
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Observation of through-space (or through-hydrogen bond) relativistic effects between a heavy element (iodine) and a hydrogen atom is reported in this work. The artwork represents a neutron star (an extremely heavy space object) that causes relativistic time effects (a connotation of Einstein's theory of relativity). A stylized spacecraft with the shape of our experimental molecule (dimethylaminopyridine) is approaching the neutron star and the interaction between its hydrogen atom and the neutron star appears. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Vícha, J.; Švec, P.; Růžičková, Z.; Samsonov, M. A.; Bártová, K.; Růžička, A.; Straka, M.; Dračínský, M. Experimental and Theoretical Evidence of Spin-Orbit Heavy Atom on the Light Atom 1H NMR Chemical Shifts Induced through H⋅⋅⋅I− Hydrogen Bond. Chem. Eur. J. 2020, 26, 8698–8702. https://doi.org/10.1002/chem.202001532
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Non-ionic polysubstituted azopyrimidines with strong push–pull character are promising candidates for extremely fast photochromic oscillators. The fast oscillation is based on photoinduced (E)-to-(Z) isomerization of the azo group and the accordingly very fast (Z)-to-(E) thermal relaxation. In their Communication on page 15590, E. Procházková, M. Cigáň et al. demonstrate how the relaxation lifetime can be tuned by proper substitution over eight orders of magnitude from hundreds of milliseconds to several nanoseconds. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Čechová, L.; Filo, J.; Dračínský, M.; Slavov, C.; Sun, D.; Janeba, Z.; Slanina, T.; Wachtveitl, J.; Procházková, E.; Cigáň, M. Polysubstituted 5-Phenylazopyrimidines: Extremely Fast Non-ionic Photochromic Oscillators. Angew. Chem. Int. Ed. 2020, 59, 15590–15594. https://doi.org/10.1002/anie.202007065
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Parallel worlds: An artistic parallel between the space-time curvature underlying gravity around a heavy magnetar with its effect on the neighboring objects in the macro world and the relativistic heavy-neighbor-atom effects on NMR shifts across the Periodic Table in the sub-nano world. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Vı́cha, J.; Novotný, J.; Komorovsky, S.; Straka, M.; Kaupp, M.; Marek, R. Relativistic Heavy-Neighbor-Atom Effects on NMR Shifts: Concepts and Trends Across the Periodic Table. Chem. Rev. 2020, 120, 7065–7103. https://doi.org/10.1021/acs.chemrev.9b00785
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A novel labeled nucleotide exerts very low near-IR fluorescence in water but lights-up (up to a 348-fold increase) after polymerase incorporation to DNA. It can be used to directly visualize enzymatic DNA synthesis in vitro and the labeled DNA probes are also responsive to secondary structure changes or interactions with small molecules or proteins. Its application was demonstrated on real-time PCR detection of RNA from SARS-CoV-2 virus. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Kuba, M.; Kraus, T.; Pohl, R.; Hocek, M. Nucleotide-Bearing Benzylidene-Tetrahydroxanthylium Near-IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions. Chem. Eur. J. 2020, 26, 11950–11954. https://doi.org/10.1002/chem.202003192 
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The front cover illustrates the cyclooxygenase (COX) highway (pathway), a part of the arachidonic acid (AA) cascade, where prostaglandins (PGE2, PGI2, PGD2, and also PGF2α) and thromboxane TXA2 are the major metabolites of AA. While inhibition of COX1/2 enzymes by NSAIDs or coxibs shuts down the whole COX highway (with some serious side-effect consequences), some of the polysubstituted pyrimidines presented in our study are able to selectively inhibit the PGE2 production, where the main molecular target of these compounds is mPGES-1. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Kalčic, F.; Kolman, V.; Ajani, H.; Zídek, Z.; Janeba, Z. Polysubstituted Pyrimidines as mPGES-1 Inhibitors: Discovery of Potent Inhibitors of PGE2 Production with Strong Anti-inflammatory Effects in Carrageenan-Induced Rat Paw Edema. ChemMedChem 2020, 15, 1398–1407. https://doi.org/10.1002/cmdc.202000258
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The front cover shows how helquat molecules (shown as solar panels) can be used as organocatalysts in the Povarov reaction. The background combines historical monuments of Prague and the new research centre of the Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, while the yellow plants represent alternative fuels. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Reyes-Gutiérrez, P. E.; Amatov, T. T.; Švec, P.; Císařová, I.; Šaman, D.; Pohl, R.; Teplý, F.; Pospíšil, L. Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids. ChemPlusChem 2020, 85, 2212–2218. https://doi.org/10.1002/cplu.202000151
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Gaur, P.; Galkin, M.; Hauke, S.; Redkin, R.; Barnes, C.; Shvadchak, V. V.; Yushchenko, D. A. Reversible spatial and temporal control of lipid signaling. Chem. Commun. 2020, 56, 10646–10649. https://doi.org/10.1039/D0CC04146G
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Matouš, P.; Kadaník, M.; Timoracký, M.; Kuneš, J.; Maříková, J.; Růžička, A.; Kočovský, P.; Pour, M. Nucleophile-assisted cyclization of β-propargylamino acrylic compounds catalyzed by gold(i): a rapid construction of multisubstituted tetrahydropyridines and their fused derivatives. Org. Chem. Front. 2020, 7, 3356–3367. https://doi.org/10.1039/D0QO00653J
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The Front Cover shows cobalt bis(dicarbollide) alkylsulfonamide, which acts as an inhibitor of carbonic anhydrase IX (CA IX). This enzyme is overexpressed on the cell surface of hypoxic cancer cells, and plays a critical role in cancer cell survival and in the formation of metastases. The inhibition of CA IX is known to result in reduced tumor growth. The new family of potent and selective CA IX inhibitors combines a structural motif of a bulky inorganic cobalt bis(dicarbollide) polyhedral ion with a propylsulfonamido anchor group. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Grüner, B.; Kugler, M.; El Anwar, S.; Holub, J.; Nekvinda, J.; Bavol, D.; Růžičková, Z.; Pospíšilová, K.; Fábry, M.; Král, V.; Brynda, J.; Řezáčová, P. Front Cover: Cobalt Bis(dicarbollide) Alkylsulfonamides: Potent and Highly Selective Inhibitors of Tumor Specific Carbonic Anhydrase IX (3/2021). ChemPlusChem 2021, 86, 347–347. https://doi.org/10.1002/cplu.202000723
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Weinstain, R.; Slanina, T.; Kand, D.; Klán, P. Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials. Chem. Rev. 2020, 120, 13135–13272. https://doi.org/10.1021/acs.chemrev.0c00663 
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