Characterization of host-guest complexes of cucurbit[n]uril (n = 6, 7) by electrospray ionization mass spectrometry

Journal of Mass Spectrometry

Volumn 41, Issue 2, 2006, Pages 202-207

  Osaka, Issey ^a   Kondou, Masanobu ^a   Selvapalam, Narayanan ^b   Samal, Shashadhar ^b   Kim, Kimoon ^b   Rekharsky, Mikhail V ^c   Inoue, Yoshihisa ^c   Arakawa, Ryuichi ^a  

^a KANSAI UNIVERSITY   (Japan)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Cucurbit n uril; ESI MS; Host guest complex

Indexed keywords

ALKALI METALS; AMMONIUM COMPOUNDS; HYDROPHOBICITY; IONIZATION; MOLECULAR STRUCTURE; POSITIVE IONS;

CUCURBIT[N]URIL; ESI-MS; HOST-GUEST COMPLEX;

MASS SPECTROMETRY;

ALKALI METAL; AMMONIA; CATION; CUCURBIT[N]URIL; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHARACTER STATE; CHEMICAL REACTION; DIPOLE; ELECTROSPRAY MASS SPECTROMETRY; GAS; HYDROPHOBICITY; PRIORITY JOURNAL;

EID: 32944473828     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.978     Document Type: Article

References (25)

1. Kim HJ, Heo J, Jeon WS, Lee E, Kim J, Sakamoto S, Yamaguchi K, Kim K. Selective inclusion of a hetero-guest pair in molecular host: formation of stable charge-transfer complexs in cucurbit[8]uril. Angew. Chem. Int. Ed. Engl 2001; 40: 1526.
2. +)2 complexs in the gas phase: influence of the guest on lid tightness. J. Am. Chem. Soc. 2001; 123: 11316.
3. Ong W, Kaifer AE. Salt effects on the apparent stability of the cucurbit[7]uril-methyl viologen inclusion complex. J. Org. Chem. 2004; 69: 1383.
4. Ong W, Kaifer MG, Kaifer AE. Cucurbit[7]uril: a very effective host for viologens and their cation radicals. Org. Lett. 2002; 4: 1791.
5. Kim HJ, Jeon WS, Ko YH, Kim K. Inclusion of methylviologen in cucurbit[7]uril. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 5007.
6. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins. 2. in vivo drug delivery. J. Pharm. Sci. 1996; 85: 1142.
7. Ashton PR, Stoddart JF, Zarzycki R. Mass spectrometric investigation of adduct formation by methylated cyclodextrins. Tetrahedron Lett. 1988; 29: 2103.
8. Camilleri P, Haskins NJ, New AP, Saunders MR. Analysing the complexation of amino acids and peptides with β-cyciodextrin using electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 1993; 7: 949.
9. Cunniff JB, Vouros P. False positives and the detection of cyclodextrin inclusion complexes by electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 1995; 6: 437.
10. Sun W, Cui M, Liu S, Song F, Elkin YN. Electrospray ionization mass spectrometry of cyclodextrin complexes with amino acids in incubated solutions and in eluates of gel permeation chromatography. Rapid Commun. Mass Spectrom. 1998; 12: 2016.
11. Lamcharfi E, Chuilon S, Kunesch G, Libot F, Virelizer H. Electrospray ionization mass spectrometry in supramolecular chemistry: characterization of non-covalent cyclodextrin complexes. J. Mass Spectrom. 1996; 31: 982.
12. Shahgholi M, Copper CL, Callahan J. Probing cyclodextrin-guest associations using electrospray mass spectrometry. J. Supramol. Chem. 1998; 9: 263.
13. Sun W, Liu J, Cui M, Song F, Liu S. Cyclodextrin-catalyzed oxidation of glutathione in solution and in an ion traps. Rapid Commun. Mass Spectrom. 1999; 13: 950.
14. Miyake K, Hirayama F, Uekama K. Solubility and mass and nuclear magnetic resonance spectroscopic studies on interaction of cyclosporin A with dimethyl-alpha- and -beta-cyclodextrins in aqueous solution. J. Pharm. Set. 1999; 88: 39.
15. Bakhtiar R. Complexes of amino (6-monodeoxy-6-mono)-beta-cyclodextrin probed by electrospray ionization mass spectrometry. Eur. Mass Spectrom. 1999; 5: 1.
16. Kobetic R, Jursic BS, Bonnette S, Tsai JSC, Salvatore SJ. Study of the lorazepam: cyclodextrin inclusion complexes using electrospray ionization mass spectrometry. Tetrahedron Lett. 2001; 42: 6077.
17. Bongiorno D, Ceraulo L, Mele A, Panzeri W, Selva A, Liveri VT. Guest-to-host proton transfer in melatonin-β-cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry. J. Mass Spectrom. 2001; 36: 1189.
18. Arakawa R, Yamaguchi T, Takahashi A, Fujimoto T, Kaneda T. Identification of face-to-face inclusion complex formation of cyclodextrin bearing an azobenzene group by electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 2003; 14: 1116.
19. Schalley CA. Supramolecular chemistry goes gas phase: the mass spectrometric examination of noncovalent interactions in host-guest chemistry and molecular recognition. Int. J. Mass Spectrom. 2000; 194: 11.
20. Kim J, Jung IS, Kim SY, Lee E, Kang JK, Sakamoto S, Yamaguchi K, Kim K. New cucurbituril homologues: synthesis, isolation, characterization, X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 2000; 122: 540.
21. Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. The cucurbit[n]uril family. Angew. Chem. Int. Ed. Engl. 2005; 44: 4844.
22. Isobe H, Sato S, Nakamura E. Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivate. Org. Lett. 2002; 4: 1287.
23. Buschmann HJ, Jansen K, Meschke C, Schollmeyer E. Thermodynamic data for complex formation between cucurbituril and alkali and alkaline earth cations in aqueous formic acid solution. J. Solution Chem. 1998; 27: 135.
24. Mock WL, Shih NY. Structure and selectivity in host-guest complexes of cucurbituril. J. Org. Chem. 1986; 51: 4440.
25. Marquez C, Hudgins RR, Nau WM. Mechanism of host-guest complexation by cucurbituril. J. Am. Chem. Soc. 2004; 16: 5806.