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Institute of organic chemistry NAS of Ukraine

PHOSPHORANES CHEMISTRY DEPARTMENT

The Department was founded in 1973 by Academician of the NASU L.M. Markovskii. Since 1988 Corresponding Member of the NASU V.I. Kalchenko is the Head of the Department. The staff of the Department is as follows: 3 Doctors of Science, 8 PhDs, 10 engineers and 3 technicians. The departments contains the Laboratory of Biomedical Researches headed by PhD. Roman V. Rodik.

Head of the Department – Dr. Sci, Professor, Corresponding Member of the National Academy of Sciences of Ukraine Vitaly I. Kalchenko

Staffs

Dr Sci., Professor Vyacheslav I. Boiko, Dr Sci., Professor Olexandr K. Yarosh, PhDr. Lyudmila I. Atamas, PhDr. Andriy B. Drapailo, PhDr. Olexandr A. Yesypenko, PhDr. Yuriy I. Matvieiev, PhDr. Olexandr V. Ruban, PhDr. Sergiy O. Cherenok, PhDr. Sergiy G. Vishnevskiy, Leading engineer Olga M. Denisenko, Ist Category engineer Lidiya S. Dovdop’yata, Ist Category engineer Darina S. Ternova, Engineer Andriy L. Boretskiy, Engineer Katerina A. Bretosh, Engineer Andriy O.Karpus, Engineer Kirilo A. Polishchuk, Engineer Lyudmila M. Savonik, Engineer Sergiy G. Kcharchenko, Engineer Anna D. Yampolska, Ist Category technician Tetyana I. Dopira, Ist Category technician Ganna O. Lisova, Ist Category technician Ganna S. Svyatnenko.

Main scientific directions. The research work is directed to the molecular design, synthesis and study of supramolecular interactions of crown-ethers, calixarenes, thiacalixarenes and calixresorcinolarenes.  The aim of investigations is creation of highly selective receptors of molecules and ions, approaching in properties to the natural enzymes, and search for their practical application.  Original types of three-dimensional macrocyclic compounds optimally prearranged for creation of supramolecular complexes with metal cations, anions and neutral organic molecules and bio-molecules, including ecologically hazardous and biologically important ones, have been synthesized.

Main scientific results. The investigations resulted in elaboration of new phosphorus-containing calixarenes which in 2-3 order of magnitude exceed the known industrial extractants (trialkylphosphineoxides, carbamoylphosphineoxides, 2-diethylhexylphosphorus acid) in selectivity and extractivity of actinides, lanthanides, platinum group metals, technetium (the main components of nuclear fuel waste).
Calixarenephosphonic  acids have been obtained. These acids effectively and (stereo)selectively inhibit alkali phosphatases, influence transportation of calcium in smooth  muscles, inhibit fibrin polymerization. These properties open paths for creation of API for medicine (in collaboration with the Institute of Bioorganic Chemistry and Petrochemistry of NASU and Palladin Biochemistry Institute of NASU).

Innovative researches

  • Effectors of Biochemical Processes
  • Modulators of Calcium Pumps in Membrane Cells
  • Cationic Calixarene Amphiphiles as Bactericides and Gene Expression Promoters
  • Calixarene Phosphine Оxide Binders of Actinides and Lanthanides
  • Enatiomericaly and Diastereochemicaly Pure Calixarenes for Chiral Technologies
  • Fluorescent Calixarenes for Chemo & BioSensors
  • Calixarene Sulfides and Thioles for Noble Metals Binding and Gold Surface Covering

More information for the innovative researches see in the Booklet Task Specific Calixarenes for Bio-Medical Research and HighTech Application

 

Сompounds which we synthesize

We are ready to perform a custom synthesis of the compounds from milligrams to kilograms quantities using our KILO LAB facility.

International projects

  • INTAS “Stereochemical Non-Rigidity and Photochromism of Four and Five Coordinate Metal Complexes”
  • INTAS “Allosteric Ionophores”
  • INTAS-UKRAINA “Detection of the Organic Solvents Vapors Using Composite Thin Films Based on Calixarenes and Conductive Polymers”
  • INCO-COPERNICUS “Development of Technologies on Efficient Decontamination of Radioactive Wastes Based on New Organophosphorus Ionophores”
  • STCU “Development and demonstration of high-level waste partitioning technology with the use of phosphorylated calixarenes”
  • STCU «Chiral calixarenes for design of hybrid organic-inorganic metallocomplexing catalysts of asymmetrical reactions”
  • STCU   “Development of chemosensor materials and equipment for detection of toxic substances and pollutants in the environment”
  • STCU   «Phosphorylated calixarenes for selective extraction of actinides from radioactive wastes»
  • STCU-NASU   «Composite calixaren-based sorbents for determination of trace radionuclides in environment»
  • CRDF “Design, synthesis and properties of calixarene based metal-organic materials, calix-MOMs”
  • NASU-CNRS GDRI “Supramolecular systems in chemistry and biology”
  • NASU-CNRS “Task-specific ionic liquids for decontamination of radioactive wastes”
  • NASU-CNRS PICS “Amphiphilic calixarenes for delivery of nucleic acids and peptides”

Selected publications

Books and chapters in monographs:

  1. V.I.Boiko, V.I.Kalchenko, О.А.Esipenko. Chiral Calixarenes. КOMPRINT. Кyiv. 2013
  2. N.A.Vodolazkaya, N.O.Mchedlov-Petrossyan, L.N.Bogdanova, R.V.Rodik, V.I. Kalchenko. The Influence of Aggregates of Calixarenes and Dendrimers on the Protolytic Equilibria of Dyes in Aqueous Solution. – In book «From molecules to functional architecture. Supramolecular interactions» / Edited by V.I. Rybachenko. – Donetsk: East Publisher House, 2013. – 538 p. – P. 49-70.
  3. S.V.Komisarenko, S.O. Kosterin, E.V.Lugovskoy, S.O. Cherenok, V.Yu. Tanchuk, A.I Vovk, V.I.Kalchenko. Synthesis and characterization of calixarene methylene bisphosphonic acids as effectors of biochemical processes.In Book: “LIGANDS: SYNTHESIS, CHARACTERIZATION AND ROLE IN BIOTECHNOLOGY”. Nova Publisher. 2013.
  4. S.V.Komisarenko, S.O.Kosterin, E.V.Lugovskoy, V.I.Kalchenko. Calixarene methylene bisphosphonic acids as promising effectors of biochemical processes. In book: Biochemistry and biotechnology for modern medicine. Publishing House O.M.Moskalenko. Kyiv. 2013.

 

Reweaves:

  1. Rodik R.V., Boyko V.I., Kalchenko V. I. Calixarenes in bio-medical researches. Current Medicinal Chemistry. – 2009. – Vol. 16, N 13. – P. 1630-1655.
  2. Cherenok S., Kalchenko V. Phosphorus-containing calixarenes. Topics Heterocyclic Chemistry. – 2009. – Vol. 20. – P. 229-273.
  3. Kalchenko V. Calixarene receptors of environmentally hazardous and bio-relevant molecules and ions. IUPAC. 2008. 80. 1449-1458
  4. Cherenok S., Dutasta J.-P., Kalchenko V. Phosphorus-containing chiral macrocycles. Current Organic Chemistry. 2006. 10. 2307-2331.

 

Articles:

  1. T.A. Cheipesh, E.S. Zagorulko, N.O. Mchedlov-Petrossyan, R.V. Rodik, V.I. Kalchenko The difference between the aggregates of short-tailed and long-tailed cationic calix[4]arene in water as detected using fluorescein dyes. Journal of Molecular Liquids. 2014 193. 232–238
  2. T. A. Veklich, A. A. Shkrabak, N. N. Slinchenko, I. I. Mazur, R. V. Rodik, V. I. Boyko V. I. Kalchenko,S. A. Kosterin CALIX[4]ARENE C-90 SELECTIVELY INHIBITS Ca2+,Mg2+_ATPase OF MYOMETRIUM CELL PLASMA MEMBRANE. Biochemistry. 2014. 79. 532 – 540.
  3. A.V. Ruban, A.B. Rozhenko, V.V. Pirozhenko, S.V. Shishkina, O.V. Shishkin, S.O. Cherenok, V.I. Kalchenko. Perfluorophenylcalix[4]arenes: perspective hosts for nucleophilic guests. Synthesis, structure and quantum chemical calculations. Tetrahedron Letters. – 2013. – V. 54. – P. 3496-3499.
  4. E. Ukhatskaya, S. V. Kurkov, M. A. Hjálmarsdóttir, V. A. Karginov, S. E. Matthews, R. V Rodik, V. I. Kalchenko, T. Loftsson. Cationic quaternized aminocalix[4]arenes: cytotoxicity, haemolytic and antibacterial activities. Int. J. Pharm. – 2013. – V. 458. – P. 25-30.
  5. A.O.Karpus, O.A.Yesypenko, L.P.Andronov, V.I.Boyko, Z.V.Voitenko, A.N.Chernega, V.I.Kalchenko.Synthesis and stereochemical configuration of inherently chiral p-tert-butylcalix[4]arene carboxylic acids and their derivatives. J. Incl. Phenom. Macrocycl Chem. – 2013. – V. 77, No 1-4. – P. 175-181.
  6. R.V.Rodik, V.Yu.Malytskyy, V.S.Starova, T.V.Yegorova, A.I.Kysil, O.A.Zaporozhets, Z.V.Voitenko, V.I.Kalchenko. Synthesis, fluorescent properties and aggregation of 2,3-dihydroisoindolenylcalix[4]arenes. J. Incl. Phenom. Macrocycl Chem. – 2013. – V. 77, No 1-4. – Р.343-350.
  7. O.I.Kalchenko, A.Drapailo, S.V.Shishkina, O.V.Shishkin, S.Kharchenko, V.Gorbatchuk, V.Kalchenko. Complexation of thiacalix[4]arene methylphоsphonic and sulfonic acids with amino acids. Supramolecular chemistry. – 2013. – V. 25, No 5. – P. 263-268.
  8. Yu.Matvieiev, V.Boyko, A.Solovyov, S.Shishkina, O.Shishkin, V.Kalchenko, A.Katz. Upper-rim calixarene phosphines consisting of multiple lower-rim OH functional groups: Synthesis and characterization. Supramol. Chem. – 2013
  9. T. A. Cheipesh, E. S. Zagorulko, N. O. Mchedlov-Petrossyan, R. V. Rodik, V. I. Kalchenko. The Difference between the Aggregates of a Short-Tailed and a Long-Tailed Cationic Calix[4]arene in Water as Detected Using Fluorescein Dyes. J. Molecular Liquids. – 2013
  10. Lyudmila V. Tsymbal, Yaroslaw D. Lampeka, Vyacheslaw I. Boyko, Vitaly I. Kalchenko, Oleg V. Shishkin. Ladder-type coordination polymer constructed from two different macrocyclic building units – calix[4]arene tetracarboxylate and hexaazamacrocyclic nickel(II) complex. Cryst. Eng. Comm. – 2013
  11. S.G.Kharchenko, А.B.Drapailo, S.V.Shishkina, О.V.Shishkin, М.D.Karavan, І.V.Smirnov, A.B.Ryabitskii, V.І.Kalchenko. Dibutylphosphinoylmethyloxythiacalix[4]arenes. Synthesis, structure, americium, europium and technetium extraction. Supramolecular Chemistry. – 2013
  12. E. Ukhatskaya, S. V. Kurkov, R. V. Rodik, V. I. Kalchenko, S. E. Matthews, P.Jansook, T. Loftsson. Surface activity and self-aggregation ability of three cationic quaternized aminocalix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. –  2013. DOI 10.1007/s10847-013-0370-6.
  13. V.V.Trush, S.O.Cherenok, V.Yu.Tanchuk, V.P.Kukhar, V.I.Kalchenko, A.I.Vovk. Calix[4]arene methylenebisphosphonic and hydroxymethylenebisphosphonic acids as inhibitors of protein tyrosine phosphatase 1B. Bioorg. Med. Chem. Lett. – 2013. – V. 23. – P. 5619-5623.
  14. S.O.Cherenok, O.A.Yushchenko, V.Yu.Tanchuk, I.M.Mischenko, N.V.Samus, O.V.Ruban, Yu.Matvieiev, Yu.A.Karpenko, V.P.Kukhar, A.I.Vovk, V.I.Kalchenko.
  15. Calix[4]arene-α-hydroxyphosphonic acids. Synthesis, stereochemistry and inhibition of glutathione S-transferase. Arkivok. – 2012. – P. 278-298.
  16. A.O.Karpus, O.A.Yesypenko, L.P.Andronov, V.I.Boyko, S.G.Garasevich, Z.V.Voitenko, A.N.Chernega, V.I.Kalchenko. Stereoselective synthesis of enantiomerically pure inherently chiral p-tert-butylcalix[4]arene carboxylic acids. Tetrahedron: Asymmetry. – 2012. – V. 23. – P.1243-1250.
  17. N.O.Mchedlov-Petrossyan, N.A.Vodolazkaya, R.V.Rodik, L.N.Bogdanova, T.A.Cheipesh, O.Yu.Soboleva, A.P.Kryshtal, L.V.Kutuzova, V.I.Kalchenko. The colloidal nature of cationic calix[4]arene aqueous solutions. J. Phys. Chem. C. – 2012. – V. 116. – P. 10245-10259.
  18. Y.I.Matvieiev, Y.A.Karpenko, A.V.Kulinich, A.B.Ryabitskii, V.G.Pivovarenko, S.V.Shishkina,O.V.Shishkin, V.I.Kalchenko. Synthesis of Calixarene-Based Ketocyanine Fluorophores. Tetrahedron Lett. – 2011. – V. 52. – P. 3922-3925
  19. R.V.Rodik, A.S.Klymchenko, N.Jain, S.I.Miroshnichenko, L.Richert, V.I.Kalchenko, Y.Mély. Virus-sized DNA nanoparticles for gene delivery based on micelles of cationic calixarenes. Chem. Eur. J. – 2011. – V.17. – P. 5526-5538.
  20. E.V.Lugovskoy, P.G.Gritsenko, T.A.Koshel, V.I.Kalchenko, S.O.Cherenok, S.V.Komisarenko. Calix[4]arene methylenebisphosphonic acids as inhibitors of fibrin polymerization. FEBS Journal. – 2011. – V. 278. – P. 1244-1251.
  21. P.Nandi, Yu.I.Matvieiev, A.Katz, V.I.Boyko, V.I.Kalchenko. A Comparative Study of Al(III)-Catalyzed MPV Reduction Using Calix[4]arenes as Oxo Ligands: Effect of Bidentate Ketone Binding. J. of Catalysis. – 2011. – V. 284, N 1. – P. 42-49.
  22. V.G.Torgov, G.A.Kostin, T.V.Us, T.M.Korda, O.V.Klimchuk, S.I.Miroshnichenko, K.Suwinska, A.A.Varnek, V.I.Kalchenko. Сalixarenes grafted with Bu2P(O)CH2O binding groups at the narrow rim: synthesis, structure and extraction of heterometallic Ru/Zn complexes. J. Incl. Phenom. Macrocycl. Chem. – 2011. – Vol. 71. – P. 67-77.
  23. F.Arnaud-Neu, M.Karavan, V.Hubscher-Bruder, I.Smirnov, V.Kalchenko. Novel phosphorylated calixarenes for the recognition of f-elements. J. Inclusion Phenomena and Macrocyclic Chemistry. – 2010. – Vol. 66, No 1-2. – P. 113-123.
  24. Vovk A.I., Kononets L.A., Tanchuk V.Yu., Drapailo A.B., Kalchenko V.I., Kukhar V.P. Thiacalix[4]arene as Molecular Platform for Design of Alkaline Phosphatase Inhibitors. J. Incl. Phenom. Macrocyclic Chem.- 2010. – V. 66, No 3-4. P. 271-277.
  25. A.I.Vovk, L.A.Kononets, V.Yu.Tanchuk, S.O.Cherenok, A.B.Drapailo, V.I.Kalchenko, V.P.Kukhar. Inhibition of Yersinia protein tyrosine phosphatise by calixarene phosphonous and methylenebisphosphonous acids. Bioorg. Med. Chem. Lett. – 2010. – Vol. 20. – P. 483–487.
  26. A.I.Vovk, L.A.Kononets, V.Yu.Tanchuk, A.B.Drapailo, V.I.Kalchenko, V.P.Kukhar. Thiacalix[4]arene as Molecular Platform for Design of Alkaline Phosphatase Inhibitors. J. Incl. Phenom. Macrocyclic Chem. – 2010. – Vol. 66. – Р. 271–277.
  27. G.A.Kostin, T.V.Us, T.M.Korda, V.G.Torgov, N.V.Kuratieva, S.I.Miroshnichenko, V.I.Kalchenko. Complexation and extraction of non-ferrous metals by calix[n]arene phosphine oxides. J. Inclusion Phenomena and Macrocyclic Chemistry. – 2010. – Vol. 68. – P. 131-137.
  28. Vovk A.I., Kononets L.A., Tanchuk V.Yu, Cherenok S.O., Drapailo A.B., Kalchenko V.I., Kukhar V.I. Inhibition of Yersinia protein tyrosine phosphatase by calixarene phosphonous and methylenebisphosphonous acids. Bioorg. Med. Chem. Lett. – 2009. – Vol. 20. – P. 483–487.
  29. Kalchenko O.I., Cherenok S.A., Solovyov A.V. Kalchenko V.I. Influence of Calixarenes on HPLC Separation of Benzene or Uracil Derivatives. Chromatographia. – 2009. – Vol. 70. – P. 717-721.
  30. Klyachina M.А., Yesypenkо O.A., Pyrozhenko V.V., Shishkina S.V., Shishkin O.V., Boyko V.І., Kalchenko V.I. Synthesis, optical resolution and absolute configuration of inherently chiral сalixarene carboxylic acids. Tetrahedron. – 2009. –Vol. 65. – P. 7085-7091.
  31. Koshets I.A., Kazantseva Z.I., Belyaev A.E., Kalchenko   V.I. Sensitivity of resorcinarene films towards aliphatic alcohols. Sensors and Actuators. – 2009. – Vol. B 140. – P. 104–108.
  32. Ha J.-M., Katz A., Drapailo A.B., Kalchenko V. I. Mercaptocalixarene-Capped Gold Nanoparticles via Postsynthetic Modification and Direct Synthesis: Effect of Calixarene Cavity-Metal Interactions. J. Phys. Chem. C.- 2009. – Vol. 113.- P. 1137-1142.
  33. Boyko V.I., Yakovenko A.V., Matvieiev Yu.I., Каlchenkо O.I., Shishkin O.V., Shishkinа S.V., Каlchenkо V.I. Regio- and stereoselective 1(S)-camphorsulfonylation of monoalkoxycalix[4]arenes. Tetrahedron. 2008. 64. 7567-7573
  34. Klyachina M.А., Boyko V.І., Yakovenko A.V., Babich L.G., Shlykov S.G., Kosterin S.О., Khilya V.P., Kalchenko V.I. Calix[4]arene N-Сhalconeamides: Synthesis and Influence on Mg2+,АТP-Dependent Са2+ Accumulation in the Smooth Muscle Subcellular Structures. J. Inclusion Phenomena and Macrocyclic Chemistry. 2008. 60. 131-137.
  35. Rodik R., Rozhenko A., Boyko V., Pirozhenko V., Danylyuk O., Suwinska K., Lipkowski J., Kalchenko V. Calix[4]arenequinazolinones. Synthesis and structure. Tetrahedron. 2007. 63. 11451-11457.
  36. Notestein J.M., Andrini L.R., Kalchenko V.I., Requejo F.J., Katz A., Iglesia E. Structural Assessment and Catalytic Consequences of the Oxygen Coordination Environment in Grafted Ti-Calixarenes. J.Am.Chem.Soc. 2007. 129. 1123-1131.
  37. Yakovenko A.V., Boyko V.I., Danylyuk O., Suwinska K., Lipkowski J., Kalchenko V.I. Diastereoselective lower rim(1S)-camphorsulfonylation as the shortest way to the inherently chiral calix[4]arene. Organic Letters. 2007. 9. 1183-1185.
  38. Yakovenko A.V., Boyko V.I., Kalchenko V.I., Baldini L., Casnati A., Sansone F., Ungaro R. N-Linked-peptidocalix[4]arene as enantioselective receptors for amino acid derivatives. J.Org.Chem. 2007. 72. 3223-3231.
  39. Kasyan O., Kalchenko V., Bolte V., Bohmer V. Hydrogen-bonded dimers of a thiacalixarene substituted carbamoylmethylphosphineoxide groups at the wide rim. Chemical Communications. 2006. 1932–1934.
  40. Cherenok S., Vovk A., Muravyova I., Shivanyuk A., Kukhar V., Lipkowski J., Kalchenko V. Calix[4]arene α-Aminophosphonic Acids: Asymmetric synthesis and Enantioselective Inhibition of Alkaline Phosphatases. Organic Letters. 2006. 8. 549-552.