Хімія, фізика та технологія поверхні, 2012, 3 (1), 3-19.

Каліксареновмісні фази в хроматографії (огляд)



O. I. Kalchenko, V. I. Kalchenko

Анотація


Огляд містить літературні дані та результати власних досліджень авторів із застосування каліксаренів як нерухомих фаз для газової та рідинної хроматографії, а також їх використання як селекторних добавок до рухомих фаз в рідинній хроматографії. Обговорюються результати та перспективи застосування каліксаренів і резорцинаренів, функціоналізованих різними групами, для хроматографічного розділення органічних та неорганічних сполук, а також механізми молекулярних взаємодій каліксаренових селекторів з аналітами різних класів, в тому числі біомолекулами.

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Gutsche C.D. Calixarenes: An introduction. Cambridge: Royal Society of Chemistry, 2008.

Lehn J.-M. Supramolecular Chemistry. Concepts and perspectives. Weinheim: Wiley–VCH, 1995.

Sansone F., Segura M., Ungaro R. Calixarenes in bioorganic and biomimetic chemistry. In Calixarenes 2001. Eds. Asfari M.-Z., Böhmer V., Harrowfield J., Vicens J. Dordrecht. Kluwer Academic Publishers, 2001. – P. 496–512.

Calixarenes for Separations .Eds. G.J. Lumetta. R.D. Rogers, A.S. Gopalan. Washington: American Chemical Society, 2000.

Vicens J., Harrowfield J., Baklouti L. Calixarenes the Nanoworld. Dordrecht: Springer, 2007.

Mildbradt R., Bohmer V. Calixarenes as stationary phases. In: Calixarenes 2001.Eds. Asfari M.–Z., Böhmer V., Harrowfield J., Vicens J. Dordrecht: Kluwer Academic Publishers, 2001.

Stewart D.R., Gutsche C.D. Isolation, сharacterization, and сonformational сharacteristics of p-tert-butylcalix [9–20] arenes. J. Am. Chem. Soc. 1999. 121. 4136–4146.

Gutsche C.D., Dhawan B., Levine J.A. et al. Conformational isomers of the ethers and esters of calyx [4] arenes. Tetrahedron. 1983. 39. 409–426.

Hoorn W. P., van Veggel F. C. J. M., Reinhoudt D. N. Conformation of exahydroxycalix [6] arene. Org. Chem. 1996. 61. 7180–7184.

Iki. N., Miyano S. Can thiacalixarene surpass calixarene. J. Incl. Phenom. 2001. 41. . 99–105.

Chauhan S. M. S., Garg B., Bisht T. Syntheses of calix[4]pyrroles by amberlyst-15 catalyzed cyclocondensations of pyrrole with selected ketones. Molecules. 2007. 12. 2458–2466.

Hu W., Li J.S., Feng Y.Q. et al. Preparation and characterization of p-tert-butyl-calix[6]arene-bonded silica gel stationary phase for high-performance liquid chromatography. Chromatographia. 1998. 48. 245–250.

Xiao X.Z., Feng Y.Q., Da S.L., Zhang Y. Preparation and evaluation of p-tert-butylcalix[4]arene-bonded silica stationary phases for high-performance liquid chromatography. Chromatographia. 1999. 49. 643–648.

Lee Y.K., Ryu Y.K., Ryu J.W. et al. Reversed-phase liquid chromatography of some positional isomers on calix[6]arene-p-sulfonate-bonded silica. Chromatographia. 1997. 46. 507–510.

Glennon J. D., O’Connor K., Srijaranai S. et al. Enhanced chromatographic selectivity for sodium(1+) ions on a calixarene-bonded silica phase. Anal. Proc. 1993. 26. 153–159.

Joyce T., Grady T., Harris S.J. et al. Chiral resolution of the enantiomers of phenylglycinol using (S)-dinaphtylprolinol calix[4]arene by capillary electrophoresis and fluorescenece spectroscopy. Anal. Commun. 1998. 35. P. 123–125.

Glennon J. D., Horne E., O’Connor K. et al. Chromatographic selectivity for amino acid esters and alkali metal ions on a silica bonded calix[4]arene tetraester stationary phase. Anal. Proc. 1994. 31. 33–35.

Glennon J.D., Horne E., Hall K. et al. Silica-bonded calixarenes in chromatography II. Chromatographic retention of metal ions and amino acid ester hydrochlorides. J. Chromatogr. A. 1996. 731. 47–55.

O'Connell M., P., Treacy J., Merly C. et al. Selective preconcentration and ion chromatography of trace lead (II) in environmental samples using a porous graphitic carbon column. Anal. Lett. 1999. 32. 185–192.

Schneider C., Menyes U., Jira T. Characterization of calixarene-bonded stationary phases . J. Sep. Sci. 2010. 33. 2930–2942.

Menyes U., Roth U., Troltzsch C. WO/1997/027479: PCT/DE1997/000180, 1997.

Mnuk P., Feltl L. Gas chromatographic study of the inclusion properties of calixarenes. I. p-tert-butylcalix[4]arene in a micropacked column. J. Chromatogr. A. 1995. 696. 101–112.

Mnuk P., Feltl L, Schurig V. Gas chromatographic study of the inclusion properties of calixarenes– II. Selective properties of cyclic tetra- to octamers derived from phenol, and some problems associated with the use of calixarenes in capillary gas chromatography . J. Chromatogr. A. 1996. 732. 63–74.

Gross B., Jauch J., Schurig V. Gas chromatographic studies employing p-(2′-methyltridecyl-2′)calix[8]arene diluted in a polysiloxane as stationary phase. J. Microcolumn Sep. 1999. 11 . 313–317.

Lai X.H., Lin L. Calix[4]arene derivatives as stationary phases for capillary gas chromatography. Chromatographia. 1998. 47. 689–694.

Lim H.J., Lee H.S., Kim I.W. et al. Separation of positional isomers on polymeric calix[4]arene-siloxane stationary phases in capillary GC. Chromatographia. 1998. 48. 422–426.

Lin L., Wu C. Y., Yan Z. Q. et al. Calix[4]arene derivatives as stationary phases for capillary gas chromatography . Chromatographia. 1998. 47. 689–694.

Lai X.H., Lin L., Wu C.Y. Preparation and chromatographic characteristics of calix[4]arene polysiloxane as stationary phases for capillary gas chromatography . Chromatographia. 1999. 50. 82–88.

Ye H., Lin L., Wu C. Two amide kinds of calix[4]arene polysiloxane stationary phases for gas chromatography. Fenxi Huaxue. 1999. 27. 1087–1090.

Xing J., Wu C.-Y., Li T. et al. Separation of aromatic isomers by capillary gas chromatography with two calix[4]arene polysiloxane stationary phases. Anal. Sci. 1999. 1715. 785–789.

Zhang L.F., Chen L., Lu X.R. et al. Chen Y.P. Preparation and study of two polysiloxanes with pendant hand-basket type calixarene stationary phases for capillary gas chromatography. J. Chromatogr. A. 1999. 840. 225–233.

Yu X.D., Lin L., Wu C.Y. Synergistic effect of mixed stationary phase in gas chromatography // Chromatographia. – 1999. – V. 49. – P. 567–571.

Park J. H., Lim H. J., Lee Y. K. et al. Separation of positional isomers on A,C- and A,D-bridged calix[6]arene as stationary phases in capillary GC // J. High Resol. Chromatogr. – 1999. – V. 222. – P. 679–682.

Pheiffer J., Schurig V. Enantiomer separation of amino acid derivatives on a new polymeric chiral calix[4]arene stationary phase by capillary gas chromatography // J. Chromatogr. A – 1999. – V. 840. – P. 145–150.

Gebauer S., Friebe S., Gubitz G., Krauss G.J., High performance liquid chromatography on calixarene-bonded silica gels. II. Separations of regio- and stereoisomers on p-tert-butylcalix[n]arene phases // J. Chromatogr. Sci. – 1998. – V. 36. – P. 383–387.

Hashem H., Jira T. The effect of the process variables on the HPLC separation of tricyclic neuroleptic on a calixarene-bonded stationary phase // Die Pharmazie. – 2005. – V. 60. – P. 186–192.

Hashem H, Jira T. Comparison of the chromatographic behavior of tricyclic neuroleptics on calixarene-bonded, monolithic and conventional RP-HPLC Columns // Comb. Chem. High Screen. – 2007. – V. 10. – P. 387–396.

Li L.S., Da S.L., Feng Y.-Q., Liu M. Study on the chromatographic behavior of water-soluble vitamins on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase by HPLC // Talanta. – 2004. – V. 64. – P. 373–379.

Liu M., Li L.-S., Da S.-L., Feng Y.-Q. High performance liquid chromatography with cyclodextrin and calixarene macrocycle bonded silica stationary phases for separation of steroids // Talanta. – 2005. – V. 66. – P. 479–486.

Gezici O., Tabakci M., Kara H., Yilmaz M. Synthesis of p-tert-Butylcalix[4]arene dinitrile bonded aminopropyl silica and investigating its usability as a stationary phase in HPLC // J. Macromol. Sci. A: Pure Appl. Chem. – 2006. – V. 43. – P. 221–231.

Gebauer S., Friebe S., Scherer C. et al. High performance liquid chromatography on calixarene-bonded silica gels. III. Separations of cis/trans isomers of proline-containing peptides // J. Chromatogr. Sci. – 1998. – V. 36. – P. 388–394.

Brindle R., Albert K., Harris S.J. et al. Silica-bonded calixarenes in chromatography. Synthesis and characterization by solid state NMR spectroscopy // J. Chromatogr. A. – 1996. – V. 731. – P. 41–46.

Glennon J.D., Horne E., Hall K. et al. Silica-bonded calixarenes in chromatography II. Chromatographic retention of metal ions and amino acid ester hydrochlorides // J. Chromatogr. A. – 1996. – V. 731. – P. 47–55.

Hutchinson S., Kearney G., Horne A. et al. Solid-phase extraction of metal-ions using immobilized chelating calixarene tetrahydroxamates // Analytica Chimica Acta. – 1994. – V. 291. – Р. 269–275.

Healy L.O., McEnery M.M., McCarthy D.G. et al. Silica-bonded calixarenes in chromatography: Enantioseparations on molecular basket phases for rapid chiral LC // Anal. Lett. – 1998. – V. 31. – P. 1543–1551.

Friebe S., Gebauer S., Krauss G.J. et al. HPLC on calixarene bonded silica gels. Characterization and applications of the p-tert-butyl-calix[4]arene bonded material // J. Chromatogr. Sci. – 1995. – V. 33. – P. 281–284.

Menyes U., Roth U. Process for the separation of fullerenes using chromatography. Eur. Pat. Appl. EP 952110. – 1999.

Menyes U., Roth U., Jira T. Separation of polycyclic aromatic hydrocarbons by using calixarene – modified chromatographic stationary phases. Eur. Pat. Appl. EP 952134. – 1999.

Iwata K., Morigushi S. (Showa Denko Kk, Japan) Jpn. Kokai Tokyo Koho 05264531 A 2. – 1993.

Iwata K., Kimizuka H., Suzuki H. (Showa Denko Kk, Japan) Jpn. Kokai Tokkyo Koho 06058920 A 2. – 1994.

Arena G., Casnati A., Contino A. et al. Synthesis of a new calixcrowns and their anchoring to silica gel for the selective separation of Cs+ and K+ // Chem. Commun. – 1996. – V. 19. – P. 2277–2278.

Sessler J.L., Genge J.W., Gale P.A., Kral V. Calix[4]pyrrole-functionalized silica gels: novel supports for the HPLC-based separation of anions // ACS Symp. Ser. – 2000. – V. 757 (Calixarenes for Separations). – P. 238.

Sessler J.L., Gale P.A., Genge J.W. Calix[4]pyrroles: new solid-phase HPLC supports for the separation of anions // Chem. Eur. J. – 1998. – N 4. – P. 1095–1099.

Li L.S., Da S.L., Feng Y.-Q., Liu M. Preparation and evaluation of a new calix[4]arene-bonded stationary phase for HPLC // J. Liq. Chromatogr. Relat. Technol. – 2004. – V. 27. – P. 2167–2188.

Sokoliess T., Menyes U., Roth. U., Jira T. Separation of cis- and trans-isomers of thioxanthene and dibenz[b,e]oxepin derivatives on calixarene- and resorcinarenebonded high-performance liquid chromatography stationary phases // J. Chromatogr. A. – 2002. – V. 948. – P. 309–319.

Sokoliess T., Schonherr J., Menyes U. et al. Characterization of calixarene- and resorcinarene-bonded stationary phases I. Hydrophobic interactions // J. Chromatogr. A. – 2003. – V. 1021. – P. 71–82.

Hashem H., Trundelberg C., Jira T. Chromatographic application on calixarene bonded stationary phases: A stability indicating LC-method for determination of Celecoxib in tablet formulation // Chromatographia. – 2010. – V. 71. – P. 91–94.

Hashem H. Chromatographic application on calixarene bonded stationary phases: A stability indicating method for simultaneous determination of paracetamol, caffeine and acetylsalicylic acid in excedrin tablets // Chromatographia. – 2010. – V. 71. – P. 31–35.

Schneider C., Jira T. Selectivity of calixarene-bonded silica phases in HPLC: Description of special characteristics with a multiple term linear equation at different methanol concentration // J. Sep. Sci. – 2010. – V. 33. – P. 2943–2955.

Li L.-S., Liu M., Da S.-L. Feng, Y.Q. The chromatographic behavior of hydroxyanthro-quinones from Rheum palmatum L. on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase by high performance liquid chromatography // Chinese J. Anal. Chem. – 2004. – V. 32, N 4. – P. 511–515.

Liu M., Da S.-L.,Feng Y.Q., Li L.-S. Preparation, characterization and chromatographic performance of p-tert-butyl-calix[8]arene bonded silica stationary phase // Chem. J. Chinese Univ. – 2004. – V. 25. – P. 1254–1256.

Li L.S., Da S.L., Feng Y.Q., Liu M. Preparation and characterization of a new p-tert-butyl-calix[8]arene-bonded stationary phase for high-performance liquid chromatography // Anal Sci. – 2004. – V. 20. – P. 561–564.

Li L.S., Da S.L., Feng Y.Q., Liu M. Separation of neutral, acidic, and basic compounds on a p-tert-butylcalix[8]arene-bonded stationary phase // Anal. Lett. – 2007. – V. 37. – P. 2805–2817.

Xiao Y.-X., Xiao X.-Z., Feng Y.-Q. et al. HPLC оf some nucleosides and bases on p-tert-butylcalix[6]arene-bonded silica gel stationary phase // J. Liq. Chromatogr. Rel. Tech. – 2001. – V. 24. – P. 2925–2942.

Sokoliess T., Menyes U., Roth U., Jira T. New calixarene-bonded stationary phases in high performance liquid chromatography: comparative studies on the retention behavior and on influences of the eluent // J. Chromatogr. A. – 2000. – V. 898. – P. 35–52.

Meyer R., Jira T. Calixarene HPLC Phases – Applications // Curr. Anal. Chem. – 2007. – V. 3. – P. 161–170.

Sliwka-Kaszynska M. Calixarenes as stationary phases in high performance liquid chromatography // Critical Reviews in analytical chemistry. – 2007. – V. 37. – P. 211–224.

Ding С., Qu K., Li Y. et al. Preparation and characterization of six calixarene bonded stationary phases for high performance liquid chromatography // Chromatogr. A. – 2007. – V. 1170. – P. 73–81.

Bazylak G., Malak A., Ali I. et al. Diversity oriented high-throughput screening of 1,3,4-oxadiazole modified chlorophenylureas and halogenobenzamides by HPLC with peptidomimetic calixarene-bonded stationary phases // Curr. Drug Discov. Technol. – 2008. – V. 5. – P. 77–89.

Krauss G.J., Friebe S., Gebauer S. Cavity supported HPLC of cis-/trans isomers of proline-containing peptides using cyclodextrins and calixarenes // J. Protein. Chem. – 1998. – V. 17. – P. 515–516.

Sessler J.L., Kim S.K., Gross D.E. et al. Crown-6-calixarene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions // J. Amer. Chem. Soc. – 2008. – V. 130. – P. 13162–13266.

Kalchenko O.I., Lipkowski J., Kalchenko V.I. et al. Effect of octakis(diethoxyphosphoryloxy)-tert-butyl-calix[8]arene in mobile phase on the reversed-phase retention behavior of aromatic compounds. Host-guest complexes formation and the stability constants determination // J. Chromatogr. Sci. – 1998. – V. 36. – P. 269–273.

Baudry R., Kalchenko O., Dumazet-Bonnamour I. et al. Investigation of host guest stability constants of calix[n]arenes complexes with aromatic molecules by RP-HPLC method // J. Chromatogr. Sci. – 2003. – V. 41. – P. 157–163.

Kalchenko O.I., Solovyov A.V., Lipkowski J., Kalchenko V.I. RP HPLC study of the complexation of benzene derivatives guest molecules with 5,17-bis(N-tolylmethylenimino)-25,27-ipropoxycalix[4]arene in acetonitrile-water solution // J. Chem. Res. (S). – 1999. – P. 60–61.

Kalchenko O.I., Бойко В.І., Яковенко А.В. та ін. Застосування рідинної хроматографії в хімії каліксаренових сполук // Матер. XXI конф. з органічної хімії (16–18 жовтня 2007 р., Чернігів, Україна). – С. 34.

Kalchenko O.I., Solovyov A.V., Lipkowski J., Kalchenko V.I. Study of the complexation of octakis(diethoxyphosphoryloxy)-tetramethyl-calix[4]-resorcinarene with benzene derivatives by RP HPLC method // J. Incl. Phenom. – 1999. – V. 34. – P. 259–266.

Kalchenko O.I., Lipkowski J., Nowakowski R. et al. Host-guest complexation of phosphorus containing calixarenes with aromatic molecules in RP HPLC conditions. The stability constants determination // J. Incl. Phenom. – 1998. – V. 23. – P. 377–380.

Lipkowski J., Kalchenko O.I., Slowikowska J. et al. Host-guest interactions of calix[4]-resorcinarenes with benzene derivatives 1 in conditions of reversed-phase high-performance liquid chromatography. Stability constants determination // J. Phys. Org. Chem. – 1998. – V. 11. – P. 426–435.

Kalchenko O., Poznanski J., Marсinowicz A. et al. Complexation of tetrapropoxycalix[4]arene with uracil and adenine derivatives in water-containing solution // J. Phys. Org. Chem. – 2003. – V. 16. – P. 246–252.

Kalchenko O., Marcinowicz A., Poznanski J. et al. Complexation of upper rim phosphorylated calix[4]arenes with uracil derivatives in water-containing solution // J. Phys. Org. Chem. – 2005. – V. 18. – P. 578–585.

Кальченко О.І., Черенок С.О., Кальченко В.І. Хроматографічне дослідження комплексоут-ворення фосфорильованих калікс[4]аренів з урацилом та аденіном // Укр. хiм. журн. – 2008. – T. 74. – C. 58–62.

Kalchenko O., Marcinowicz A., Poznanski J. et al. HPLC Investigation of complexation of calixarenes with uracil derivatives // Int. Conf. “Modern Physical Chemistry for Advanced materials” devoted to the 100th anniversаry of the birth of Professor N. Izmailov (June 26-30, 2007, Kharkiv, Ukraine). Book of Abstracts – P. 56.

Kalchenko O.I., Perret F., Coleman A.W. A comparative study of the determination of the stability constants of inclusion complexes of p-sulphonato-calix[4]arene with aminoacids by RP HPLC and 1H NMR // J. Chem. Soc. Perkin Trans. 2. – 2001. – Р. 258–263.

Douteau-Guevel N., Coleman A.W., Morel J.-P., Morel-Desrosiers N. Complexation of the basic aminoacids lysine and arginine by three sulfonatocalix[n]arenas (n=4, 6 and 8) in water: microcalorimetric determination of the Gibbs energies, enthalpies and entropies of complexation // J. Chem. Soc., Perkin Trans. 2. – 1999. – P. 629–633.

Кальченко О.І., Da Silva E., Coleman A.W. Determination of the stability constants of inclusion complexes of p-H-37-(carboxy-methyloxy)-calix-[6]-arene and p-sulphonato-37-(2-carboxy-methyloxy)-calix-[6]-arene with 15 amino acids by RP HPLC // J. Incl. Phenom. – 2002. – V. 43. – P. 305–310.

Патент України № а 01243 Етилгілрокси-фосфонілметилтетра-пропоксика-лікс[4]арен в якості комплексоутворювача амінокислот / Кальченко О.І, Mірошніченко C.І., Кальченко В.І. – 2007.

Патент України № а 01246 Натрова сіль дигідрокси-фосфонілметилтіакалікс[4]арену в якості комплексоутворювача амінокислот / Касьян О.В., Драпайло А.Б., Кальченко О.І., Кальченко В.І. – 2007.

Кальченко О.І., Кальченко В.І. Рідинна хроматографія в аналітичній та супрамоле-кулярній хімії каліксаренів // Журнал орг. фарм. хімії. – 2011. –Т.9. – C. 21–36.

Cherenok S.O., Міrоshnichеnkо S.І., Drаpаilо А.B. et al. Supramolecular chemistry of phosphorus containing (thia)calixarenes // 18th Int. conf. of phosphorus chemistry (July 11–15, 2010, Wroclaw, Poland). Book of Abstracts – P. 55.

Кальченко О.І., Касьян О.В., Драпайло А.Б. и др. Синтез та хроматографічне дослідження комплексоутворення водорозчинних каліксаренів з амінокислотами // “Актуальні проблеми синтезу і створення нових біологічно активних сполук та фармацевтичних препаратів” (15–18 жовтня 2008 р., Львів, Україна). Матеріали: Національна науково-технічна конференція – С.163.

Carugo O. Prediction of polypeptide fragments exposed to the solvent // In Silico Biology. – 2003. – V. 3. – P. 0035–0045.

Шкрабак O.A., Kaльчeнкo O.I., Рoдiк Р.В. та ін. Каліксарензалежний гідроліз АТР. I. Кінетика реакції та комплексоутворення між каліксареном С-107 та нуклеозидтрифос-фатом // Укр. бioхiм. журн. – 2008. – Т. 80. – С. 90–99.

Rodik R.V., Kаlchеnkо О.І., Boyko V.I. et al. Influence of calixareneaminomethylphosphonic acids on ATP hydrolisys // Book of Abstracts: Vth International Symposium Supramolecular Systems in Chemistry and Biology (May 12–17, 2009, Kyiv, Ukraine). – P. 171.

Rodik R.V., Kalchenko O.I., Boyko V.I. et al. ynthesis and ATP- Hydrolase Activity of Calixarene-aminomethyl-phosphonic acids // XVth International Conference on Chemstry of Phosphorus Compounds (ІССРС-XV) (May 25–31, 2008, Saint-Petersburg, Russia). Book of Abstracts – P. 425.

Kаlchеnkо О.І., Cherenok S.O., Rodik R.V. et al. HPLC study of the complexation of phosphorus and sulfur containing calixarenes with aminoacids // 3rd Summer School „Supramolecular Systems in Chemistry and Biology” (September 6–10, 2010). Book of Abstracts – P. 89.

Cherenok S.O., Yuschenko O.A., Gritsenko P.G. et al. Synthesis of calix[4]arenemethylene-bisphosphonic acids and their influence on fibrin polymerization // Phosphorus, Sulfur, Silicon and the Related Elements – 2011. – V. 186 – P. 1–2.

Lugovskoy E.V., Gritsenko P.G. , Koshel T.A. et al. Calix[4]arene methylenebisphosphonic acids as inhibitors of fibrin polymerization // FEBS Journal. – 2011. – V. 278. – P. 1244–1251.

Kalchenko O.I., Cherenok S.A., Kаlchеnkо V.І. Influence of calixarenes on chromatographic separation of benzene or uracil derivatives // Chromatographia. – 2009. – V. 70. – P. 717–721.

Kalchenko O., Cherenok S., Solovyov A., Kalchenko V. Influence of calixarenes on HPLC separation of aromatic molecules // First Int. Symp. ”Supramolecular and NanoChemistry: Toward Applications” (SNCTA–2008) (August 25–29, 2008, Kharkiv, Ukraine). Book of Abstracts – Р. 1–8.




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