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Collect. Czech. Chem. Commun. 2000, 65, 1289-1316
https://doi.org/10.1135/cccc20001289

Bis(methylphosphonic Acid) Derivatives of 1,4,8,11-Tetraazacyclotetradecane (Cyclam). Synthesis, Crystal and Molecular Structures, and Solution Properties

Jan Kotek, Pavel Vojtíšek, Ivana Císařová, Petr Hermann*, Petr Jurečka, Jan Rohovec and Ivan Lukeš

Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic

Crossref Cited-by Linking

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  • Kotková Zuzana, Koucký Filip, Kotek Jan, Císařová Ivana, Parker David, Hermann Petr: Copper(ii) complexes of cyclams with N-(2,2,2-trifluoroethyl)-aminoalkyl pendant arms as potential probes for 19F magnetic resonance imaging. Dalton Trans. 2023, 52, 1861. <https://doi.org/10.1039/D2DT03360G>
  • Koucký Filip, Kotek Jan, Císařová Ivana, Havlíčková Jana, Kubíček Vojtěch, Hermann Petr: Transition metal complexes of cyclam with two 2,2,2-trifluoroethylphosphinate pendant arms as probes for 19F magnetic resonance imaging. Dalton Trans. 2023, 52, 12208. <https://doi.org/10.1039/D3DT01420G>
  • Pazderová Lucia, Benešová Martina, Havlíčková Jana, Vojtíčková Margareta, Kotek Jan, Lubal Přemysl, Ullrich Martin, Walther Martin, Schulze Sabine, Neuber Christin, Rammelt Stefan, Pietzsch Hans-Jürgen, Pietzsch Jens, Kubíček Vojtěch, Hermann Petr: Cyclam with a phosphinate-bis(phosphonate) pendant arm is a bone-targeting carrier of copper radionuclides. Dalton Trans. 2022, 51, 9541. <https://doi.org/10.1039/D2DT01172G>
  • Pazderová Lucia, David Tomáš, Hlinová Veronika, Plutnar Jan, Kotek Jan, Lubal Přemysl, Kubíček Vojtěch, Hermann Petr: Cross-Bridged Cyclam with Phosphonate and Phosphinate Pendant Arms: Chelators for Copper Radioisotopes with Fast Complexation. Inorg. Chem. 2020, 59, 8432. <https://doi.org/10.1021/acs.inorgchem.0c00856>
  • Taschner Ian S., Aubuchon Ethan, Schrage Briana R., Ziegler Christopher J., van der Est Art: Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms. Dalton Trans. 2020, 49, 3545. <https://doi.org/10.1039/C9DT04869C>
  • Bárta Jiří, Hermann Petr, Kotek Jan: Coordination Behavior of 1,4-Disubstituted Cyclen Endowed with Phosphonate, Phosphonate Monoethylester, and H-Phosphinate Pendant Arms. Molecules 2019, 24, 3324. <https://doi.org/10.3390/molecules24183324>
  • Hlinová Veronika, Jaroš Adam, David Tomáš, Císařová Ivana, Kotek Jan, Kubíček Vojtěch, Hermann Petr: Complexes of phosphonate and phosphinate derivatives of dipicolylamine. New J. Chem. 2018, 42, 7713. <https://doi.org/10.1039/C8NJ00100F>
  • Paúrová Monika, David Tomáš, Císařová Ivana, Lubal Přemysl, Hermann Petr, Kotek Jan: Optimization of the selectivity and rate of copper radioisotope complexation: formation and dissociation kinetic studies of 1,4,8-trimethylcyclam-based ligands with different coordinating pendant arms. New J. Chem. 2018, 42, 11908. <https://doi.org/10.1039/C8NJ00419F>
  • Blahut Jan, Hermann Petr, Gálisová Andrea, Herynek Vít, Císařová Ivana, Tošner Zdeněk, Kotek Jan: Nickel(ii) complexes of N-CH2CF3 cyclam derivatives as contrast agents for 19F magnetic resonance imaging. Dalton Trans. 2016, 45, 474. <https://doi.org/10.1039/C5DT04138D>
  • Paúrová Monika, Havlíčková Jana, Pospíšilová Aneta, Vetrík Miroslav, Císařová Ivana, Stephan Holger, Pietzsch Hans‐Jürgen, Hrubý Martin, Hermann Petr, Kotek Jan: Bifunctional Cyclam‐Based Ligands with Phosphorus Acid Pendant Moieties for Radiocopper Separation: Thermodynamic and Kinetic Studies. Chemistry A European J 2015, 21, 4671. <https://doi.org/10.1002/chem.201405777>
  • Lima Luís M. P., Esteves Catarina V., Delgado Rita, Hermann Petr, Kotek Jan, Ševčíková Romana, Lubal Přemysl: Tris(phosphonomethyl) Cyclen Derivatives: Synthesis, Acid–Base Properties and Complexation Studies with Cu2+ and Zn2+ Ions. Eur J Inorg Chem 2012, 2012, 2533. <https://doi.org/10.1002/ejic.201101334>
  • Lima Luís M. P., Delgado Rita, Plutnar Jan, Hermann Petr, Kotek Jan: A New Tris(phosphonomethyl) Monoacetic Acid Cyclam Derivative: Synthesis, Acid‐Base and Metal Complexation Studies. Eur J Inorg Chem 2011, 2011, 527. <https://doi.org/10.1002/ejic.201000919>
  • Campello M. Paula C., Lacerda Sara, Santos Isabel C., Pereira Giovannia A., Geraldes Carlos F. G. C., Kotek Jan, Hermann Petr, Vaněk Jakub, Lubal Přemysl, Kubíček  Vojtěch, Tóth Éva, Santos Isabel: Lanthanide(III) Complexes of 4,10‐Bis(phosphonomethyl)‐1,4,7,10‐tetraazacyclododecane‐1,7‐diacetic acid (trans‐H6do2a2p) in Solution and in the Solid State: Structural Studies Along the Series. Chemistry A European J 2010, 16, 8446. <https://doi.org/10.1002/chem.201000320>
  • Chang John Yu-Chih, Stevenson Ralph J., Lu Guo-Liang, Brothers Penelope J., Clark George R., Denny William A., Ware David C.: Syntheses of 8-quinolinolatocobalt(iii) complexes containing cyclen based auxiliary ligands as models for hypoxia-activated prodrugs. Dalton Trans. 2010, 39, 11535. <https://doi.org/10.1039/c0dt01142h>
  • Svobodová Ivona, Havlíčková Jana, Plutnar Jan, Lubal Přemysl, Kotek Jan, Hermann Petr: Metal Complexes of 4,11‐Dimethyl‐1,4,8,11‐tetraazacyclotetradecane‐1,8‐bis(methylphosphonic acid) – Thermodynamic and Formation/Decomplexation Kinetic Studies. Eur J Inorg Chem 2009, 2009, 3577. <https://doi.org/10.1002/ejic.200900358>
  • Boswell C. Andrew, Regino Celeste A.S., Baidoo Kwamena E., Wong Karen J., Milenic Diane E., Kelley James A., Lai Christopher C., Brechbiel Martin W.: A novel side-bridged hybrid phosphonate/acetate pendant cyclam: Synthesis, characterization, and 64Cu small animal PET imaging. biorg med chem 2009, 17, 548. <https://doi.org/10.1016/j.bmc.2008.11.073>
  • Kreher Ute, Hearn Milton T. W., Spiccia Leone: X-Ray Crystal Structure, Acid - Base Properties and Complexation Characteristics of a Methylenephosphonate Derivative of 1,4,7,10-Tetraazacyclododecane. Aust. J. Chem. 2009, 62, 1583. <https://doi.org/10.1071/CH09337>
  • Plutnar Jan, Havlíčková Jana, Kotek Jan, Hermann Petr, Lukeš Ivan: Unsymmetrically substituted side-bridged cyclam derivatives and their Cu(ii) and Zn(ii) complexes. New J. Chem. 2008, 32, 496. <https://doi.org/10.1039/B709747F>
  • Havlíčková Jana, Medová Hana, Vitha Tomáš, Kotek Jan, Císařová Ivana, Hermann Petr: Coordination properties of cyclam (1,4,8,11-tetraazacyclotetradecane) endowed with two methylphosphonic acid pendant arms in the 1,4-positions. Dalton Trans. 2008, 5378. <https://doi.org/10.1039/b803235a>
  • Lima Luís M. P., Delgado Rita, Drew Michael G. B., Brandão Paula, Félix Vítor: Cyclam derivatives containing three acetate pendant arms: synthesis, acid–base, metal complexation and structural studies. Dalton Trans. 2008, 6593. <https://doi.org/10.1039/b809100e>
  • Dehghanpour Saeed, Mahmoudi Ali, Khalaj Mehdi: Zwitterionic (4-benzylpiperidinium-1-ylmethyl)phosphonate. Acta Crystallogr E Struct Rep Online 2008, 64, o19. <https://doi.org/10.1107/S1600536807061429>
  • Försterová Michaela, Svobodová Ivona, Lubal Přemysl, Táborský Petr, Kotek Jan, Hermann Petr, Lukeš Ivan: Thermodynamic study of lanthanide(iii) complexes with bifunctional monophosphinic acid analogues of H4dota and comparative kinetic study of yttrium(iii) complexes. Dalton Trans. 2007, 535. <https://doi.org/10.1039/B613404A>
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  • Lubal P., Maleček J., Hermann P., Kotek J., Havel J.: Capillary electrophoretic separation and kinetic study of inert copper(II) complexes of 1,8-bis(methylphosphonate) derivative of cyclam. J Polyhedron 2006, 25, 1884. <https://doi.org/10.1016/j.poly.2005.12.004>
  • Yamasaki Ryu, Tanatani Aya, Azumaya Isao, Masu Hyuma, Yamaguchi Kentaro, Kagechika Hiroyuki: Solvent-Dependent Conformational Switching of N-Phenylhydroxamic Acid and Its Application in Crystal Engineering. Crystal Growth & Design 2006, 6, 2007. <https://doi.org/10.1021/cg060151z>
  • Svobodová Ivona, Lubal Přemysl, Plutnar Jan, Havlíčková Jana, Kotek Jan, Hermann Petr, Lukeš Ivan: Thermodynamic, kinetic and solid-state study of divalent metal complexes of 1,4,8,11-tetraazacyclotetradecane (cyclam) bearing two trans (1,8-)methylphosphonic acid pendant arms. Dalton Trans. 2006, 5184. <https://doi.org/10.1039/B603251F>
  • Vitha Tomáš, Kotek Jan, Rudovský Jakub, Kubíček Vojtěch, Císařová Ivana, Hermann Petr, Lukeš Ivan: Selective Protection of 1,4,8,11-Tetraazacyclotetradecane (Cyclam) in Position 1,4 with the Phosphonothioyl Group and Synthesis of a Cyclam-1,4-bis(methylphosphonic Acid). Crystal Structures of Several Cyclic Phosphonothioamides. Collect. Czech. Chem. Commun. 2006, 71, 337. <https://doi.org/10.1135/cccc20060337>
  • Füzerová Silvia, Kotek Jan, Císařová Ivana, Hermann Petr, Binnemans Koen, Lukeš Ivan: Cyclam (1,4,8,11-tetraazacyclotetradecane) with one methylphosphonate pendant arm: a new ligand for selective copper(ii) binding. Dalton Trans. 2005, 2908. <https://doi.org/10.1039/b507062g>
  • Táborský Petr, Lubal Přemysl, Havel Josef, Kotek Jan, Hermann Petr, Lukeš Ivan: Thermodynamic and Kinetic Studies of Lanthanide(III) Complexes with H5do3ap (1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic-10-(methylphosphonic Acid)), a Monophosphonate Analogue of H4dota. Collect. Czech. Chem. Commun. 2005, 70, 1909. <https://doi.org/10.1135/cccc20051909>
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  • Fensterbank Hélène, Berthault Patrick, Larpent Chantal: A Tunable One‐Step N,N′‐Disubstitution of 1,4,8,11‐Tetraazacyclotetradecane with Acrylamide. Eur J Org Chem 2003, 2003, 3985. <https://doi.org/10.1002/ejoc.200300133>
  • Kubíček Vojtěch, Vojtíšek Pavel, Rudovský Jakub, Hermann Petr, Lukeš Ivan: Complexes of divalent transition metal ions with bis(aminomethyl)phosphinic acid in aqueous solution and in the solid state. Dalton Trans. 2003, 3927. <https://doi.org/10.1039/B305844A>
  • Kotek Jan, Vojtisek Pavel, Cisarova Ivana, Hermann Petr, Jurecka Petr, Rohovec Jan, Lukes Ivan: ChemInform Abstract: Bis(methylphosphonic acid) Derivatives of 1,4,8,11‐Tetraazacyclotetradecane (Cyclam). Synthesis, Crystal and Molecular Structures, and Solution Properties. ChemInform 2001, 32. <https://doi.org/10.1002/chin.200105133>
  • Kotek Jan, Hermann Petr, Cı́sařová Ivana, Rohovec Jan, Lukeš Ivan: The cis/trans-isomerism on cobalt(III) complexes with 1,4,8,11-tetraazacyclotetradecane-1,8-bis(methylphosphonic acid). Inorganica Chimica Acta 2001, 317, 324. <https://doi.org/10.1016/S0020-1693(01)00348-6>
  • Lubal Přemysl, Kývala Mojmı́r, Hermann Petr, Holubová Jana, Rohovec Jan, Havel Josef, Lukeš Ivan: Thermodynamic and kinetic study of copper(II) complexes with N-methylene(phenylphosphinic acid) derivatives of cyclen and cyclam. Polyhedron 2001, 20, 47. <https://doi.org/10.1016/S0277-5387(00)00586-6>
  • Kotek Jan, Vojtíšek Pavel, Císařová Ivana, Hermann Petr, Lukeš Ivan: Unusual cis/trans Isomerism in Octahedral Nickel(II) Complexes with 1,4,8,11-Tetraazacyclotetradecane-1,8-bis(methylphosphonic Acid) as a Ligand. Collect. Czech. Chem. Commun. 2001, 66, 363. <https://doi.org/10.1135/cccc20010363>