Emerging subject for chiral separation science: Cluster boron compounds

Chirality

Volumn 23, Issue 4, 2011, Pages 307-319

  Horáková, Hana ^a   Grüner, Bohumír ^b   Vespalec, Radim ^c,d  

^a BRNO UNIVERSITY OF TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

^c Kachlíkova   (Czech Republic)

^d Radim Vespalec   (Czech Republic)

Author keywords

boranes; capillary electrophoresis; carboranes; chiral separations; cyclodextrins; liquid chromatography

Indexed keywords

BORON; CARBORANE DERIVATIVE; CYCLODEXTRIN; METALLACARBORANE DERIVATIVE; UNCLASSIFIED DRUG;

CHIRALITY; DATA BASE; ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REVIEW;

EID: 79952496460     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20918     Document Type: Review

References (47)

1. Plesek J,. Potential applications of the boron cluster compounds. Chem Rev 1992; 92: 269-278.
2. Grimes RN,. Boron clusters come of age. J Chem Educ 2004; 81: 658-672.
3. Valliant IF, Guenther KJ, King AS, Morel P, Schaffer P, Sogbein OO, Stephenson KA,. The medicinal chemistry of carboranes. Coord Chem Rev 2002; 232: 173-230.
4. Armstrong AF, Valliant JF,. The bioorganic and medicinal chemistry of carboranes: from new drug discovery to molecular imaging and therapy. Dalton Trans 2007: 4240-4251. (Pubitemid 47485645)
5. Endo Y, Yoshimi T, Miyaura C,. Utility of boron clusters for drug design: selective estrogen receptor modulators (SERMs) bearing carborane as a hydrophobic skeletal structure. In:, Bubnov Yu, editor. Boron Chemistry at the Beginning of the 21-st Century. Proceedings of the 11-th international conference on the chemistry of boron, IMEBORON XI. Moscow: Editorial URSS Scientific Literature and Textbooks; 2002. p. 298-306.
6. Cigler P, Kozisek M, Rezacova P, Brynda J, Otwinowski, Z, Pokorna J, Plesek J, Gruner B, Doleckova-Maresova L, Masa M, Sedlacek J, Bodem J, Krausslich HG, Kral V, Konvalinka J,. From nonpeptide toward noncarbon protease inhibitors: metallacarboranes as specific and potent inhibitors of HIV protease. Proc Natl Acad Sci USA 2005; 102: 15394-15399. (Pubitemid 41528068)
7. KoÅíÅek M., Cígler P, LepÅík M, Fanfrlík J, ÅezáÄová P, Brynda J, Pokorná J, PleÅek J, Grüner B, Grantz-ÅaÅková K, Václavíková J, Kraeusslich HG, Král V, Konvalinka J,. Inorganic polyhedral metallacarborane inhibitors of HIV protease a new approach to overcoming antiviral resistance. J Med Chem 2008; 59: 4839-4843.
8. Soloway AH, Barth RF, Gahbauer RA, Blue TE, Goodman JH,. The rationale requirements for the development of boron neutron capture therapy of brain tumors. J Neurol Oncol 1997; 33: 9-13.
9. Hawthorne MF,. New horizons for therapy based on the boron neutron capture reaction. Mol Med Today 1998; 4: 174-181. (Pubitemid 28207733)
10. Hawthorne MF,. The role of chemistry in the development of boron neutron-capture therapy of cancer. Angew Chemie Intl Ed Engl 1993; 32: 950-984.
11. Teixidor F, Viñas C, Democeanu A, Nunez R,. Boron clusters: Do they receive the deserved interest? Pure Appl Chem 2003; 75: 1305-1313.
12. Teixidor F, Flores MA, Vinas C,. The first optically pure nido monothiocarborane cluster. Organometalics 1999; 18: 5409-5411. (Pubitemid 129648919)
13. 11] and its ortho-cycloboronated derivative. Inorg Chem Commun 2005; 8: 614-618. (Pubitemid 40792971)
14. Williams RE,. The polyborane, carborane, carbocation continuum: architectural patterns. Chem Rev 1992; 92: 177-207.
15. Williams RE,. In:, Casanova E, editor. The borane, carbaborane and carbocation continuum. New York: John Wiley; 1997. p 3-57.
16. PleÅek J,. Chemistry of deltahedral compounds of boron and organic chemistry. Fundamental similarity and fundamental dissimilarity (in Czech). Chem Listy 1996; 90: 273-279.
17. PleÅek J,. The age of chiral deltahedral boranes. Inorg Chim Acta 1999; 289: 45-50.
18. Fanfrlik J, Lepsik M, Havlas Z, Hobza P,. Interaction of carboranes with biomolecules: Formation of dihydrogen bonds. Chem Phys Chem 2006; 7: 1100-1105.
19. Juhasz M, Hoffmann S, Stoyanov E, Kim KC, Reed CA,. The strongest isolable acid. Angew Chem Intl Ed Engl 2004; 43: 5352-5355. (Pubitemid 39433916)
20. - and its protonated zwitterionic product. J Sep Sci 2007; 30: 2733-2741. (Pubitemid 350162210)
21. Grüner, B, Plzák Z,. High performance liquid chromatographic separations of boron cluster compounds. J Chromatogr A 1997; 789: 497-517. (Pubitemid 28028221)
22. Vespalec R, BoÄek P,. Chiral separations in capillary electrophoresis. Chem Rev 2000; 100: 3715-3753.
23. Chankvetadze B,. Capillary electrophoresis in chiral analysis. Chichester: John Wiley & Sons; 1997. 555 p.
24. PleÅek J, Grüner B, MaloÅ P,. Liquid chromatographic resolution of enantiomers of deltahedral carborane and metallaborane derivatives. J Chromatogr 1992; 626: 197-206.
25. 10. Collect Czech Chem Commun 1993; 58: 1087-1092.
26. 2-2-Co] with a monosulfur bridge between ligands and HPLC resolution of the enantiomers. Collect Czech Chem Commun 1993; 58: 2936-2943.
27. PleÅek J, Grüner B, VanÄk T, Votavová H,. Chiral resolution of enantiomers of asymmetric cobaltacarboranes with monoatomic bridge between ligands by liquid chromatography on a Ã-cyclodextrin column. J Chromatogr 1993c; 633: 73-80.
28. 2-3-Co] complex-the third isomer of nitrogen-bridged bisicosahedral cobaltacarborane. Collect Czech Chem Commun 1994; 59: 347-380.
29. Grüner B, Holub J, PleÅek J, VanÄk T, Votavová H,. High-performance liquid chromatographic enantiomeric resolution in the ten-vertex carborane series. Comparison of acetyl- and native-cyclodextrin bonded chiral stationary phases. J Chromatogr A 1998a; 793: 249-256. (Pubitemid 28044250)
30. 2-2-Co] bridged cobaltacarborane to enantiomers pure by HPLC, circular dichroism spectra and absolute configuration by X-ray diffraction. Tetrahedron: Asymmetry 1998b; 9: 79-88. (Pubitemid 28096377)
31. 9]. J Organomet Chem 2000: 1-14.
32. Petersson P, Malmquist J, Markides KE, Sjoberg S,. Determination of enantiomeric purity of (S)-carboranylalanine using capillary column supercritical- fluid chromatography. J. Chromatogr. A, 1994; 670: 239-242. (Pubitemid 24179150)
33. 3,2-norbornadienyl) rhodacarboranes into enantiomers by HLPC on chiral stationary phases. Russ Chem Bull 2000; 49: 759-760.
34. Valliant JF, Schaffer P, Stephenson KA, Britten JF,. Synthesis of boroxifen, a nido-carborane analogue of tamoxifen. J Org Chem 2002; 67: 383-387. (Pubitemid 34101239)
35. Ramsay BO,. Stereochemistry. London: Heyden; 1990. 486 p.
36. SlavíÄek V, Grüner B, Vespalec R,. Exploration of the electrophoretic behavior of borane cluster anions and of the capability capillary electrophoresis to separate them chirally. J Chromatogr A 2003; 984: 121-134. (Pubitemid 35453934)
37. Horáková H, Vespalec R,. Chiral separability of hydrophobic boron cluster anions with native cyclodextrins in water-methanol background electrolytes. Electrophoresis 2007; 28: 3639-3649. (Pubitemid 350056192)
38. Horáková H, Vespalec R,. Influence of substituents on selectivity and efficiency of chiral separations of anions containing single nido-7,8-dicarbaundecaborane cluster with α-cyclodextrin. J Chromatogr A 2007; 1143: 143-152. (Pubitemid 46209111)
39. Horáková H, Grüner B, Vespalec R,. Preconditions for reasonable detection sensitivity and zone symmetry in electrophoretic separations of cluster borane anions. J Chromatogr A 2004; 1051: 227-235. (Pubitemid 39298848)
40. Valeri AR, Kremser L, Raggi MA, Grüner B, Vespalec R, Kenndler E,. Capillary electrophoresis of boron cluster compounds in aqueous and nonaqueous solvents. Electrophoresis 2008; 29: 1658-1666. (Pubitemid 351597524)
41. Horáková H, Vespalec R,. Optical spectra of anionic boron cluster compounds and their utilization for photometric detection. Spectrochim Acta A 2006; 65: 378-386. (Pubitemid 44292578)
42. Cameron J, Macka M, Haddad PR,. Enhancement of detection sensitivity for indirect photometric detection of anions and cations in capillary electrophoresis. Electrophoresis 2003; 24: 2150-2167. (Pubitemid 38088997)
43. Wren SAC, Rowe, RC,. Theoretical aspects of chiral separation in capillary electrophoresis I. Initial evaluation of model. J Chromatogr 1992; 603: 235-241.
44. Wren SAC, Rowe RC,. Theoretical aspects of chiral separation in capillary electrophoresis II. The role of organic solvent. J Chromatogr 1992; 609: 363-367.
45. Wren SAC, Rowe RC,. 1993. Theoretical aspects of chiral separation in capillary electrophoresis III. Application to Ã-blockers. J Chromatogr 1993; 635: 113-118. (Pubitemid 23112137)
46. Giddingd JC,. Unified separation science. New York: Wiley; 1991.
47. KrupÄík J, Oswald P, Májek P, Sandra P, Armstrong DW,. Determination of the interconversion energy barriers by separation methods. J. Chromatogr A 2003; 1000: 779-800. (Pubitemid 36638485)