Determination of branched β-cyclodextrin-prostaglandin complexes using electrospray ionization mass spectrometry

Bioscience, Biotechnology and Biochemistry

Volumn 72, Issue 8, 2008, Pages 2164-2169

  Yamane, Naoe ^a   Tozuka, Zenzaburo ^a   Okada, Yasuyo ^b   Honda, Chie ^b   Nishi, Yuki ^b   Tanimoto, Toshiko ^b  

^a JCL Bioassay Corporation   (Japan)

^b MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

Author keywords

Branched cyclodextrin; Electrospray ionization mass spectrometry; Inclusion complex; Prostaglandin

Indexed keywords

CHLORINE COMPOUNDS; DATA STORAGE EQUIPMENT; IONIZATION; MASS SPECTROMETERS; MASS SPECTROMETRY; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS;

CYCLO DEXTRIN; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; INCLUSION COMPLEX; PROSTAGLANDIN;

ELECTROSPRAY IONIZATION;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; PROSTAGLANDIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY;

BETA-CYCLODEXTRINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROSTAGLANDINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 50649102624     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80233     Document Type: Article

References (33)

1. Szejtli, J., "Cyclodextrins and Their Inclusion Complexes," Akademiani Kiado, Budapest (1982).
2. Uekama, K., and Otagiri, M., Cyclodextrins in drug carrier systems. CRC Critical Reviews in Therapeutic Drug Carrier Systems, 3, 1-40 (1987).
3. Szejtli, J., Medicinal applications of cyclodextrins. Med. Res. Rev., 14, 353-386 (1994).
4. Okada, Y., Matsuda, K., Hara, K., Hamayasu, K., Hashimoto, H., and Koizumi, K., Properties and the inclusion behavior of 6-O-α- D-galactosyl- and 6-O-α-D-mannosyl-cyclodextrins. Chem. Pharm. Bull., 47, 1564-1568 (1999).
5. 2α with α- and β-cyclodextrin in aqueous solution. Chem. Pharm. Bull., 26, 1195-1200 (1978).
6. Uekama, K., Hirayama, F., Yamasaki, S., Otagiri, M., and Ikeda, K., Circular dichroism study on inclusion complexes of some prostagalandins with α- and β-cyclodextrins. Chem. Lett., 1389-1392 (1977).
7. 1 with α-cyclodextrin in aqueous systems: stability of the inclusion complex. J. Pharm. Sci., 80, 153-156 (1991).
8. 2α-cyclodextrin complexes in aqueous solution. Chem. Pharm. Bull., 28, 1975-1980 (1980).
9. Koizumi, K., and Utamura, T., Isolation and characterization of branched cyclodextrins. Carbohydr. Res., 153, 55-67 (1986).
10. Yamagaki, T., Ishizuka, Y., Kawabata, S., and Nakanishi, H., Post-source decay fragment spectra of cyclomalto-octaose and branched cyclomalto-hexaose by matrix-assisted laser desorption/ionization time-of flight mass spectrometry. Rapid Commun. Mass Spectrom., 10, 1887-1890 (1996).
11. Lehmann, E., Salih, B., Gomez-Lopez, M., Diederich, F., and Zenobi, R., Do matrix-assisted laser desorption/ioniation mass spectra reflect solution-phase formation of cyclodextrin inclusion complexes? Analyst, 125, 849-854 (2000).
12. Zhang, M., Shi, Z., Bai, Y., Gao, Y., Hu, R., and Zhao, F., Using molecular recognition of β-cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry. J. Am. Soc. Mass Spectrom., 17, 189-193 (2006).
13. Ganem, B., Li, Y. T., and Henion, J. D., Detection of noncovalent receptor-ligand complexes by mass spectrometry. J. Am. Chem. Soc., 113, 6294-6296 (1991).
14. th, 226-232 (1992).
15. Haskins, N. J., Saunders, M. R., and Camilleri, P., The complexation and chiral selectivity of 2-hydroxypropyl-β-cyclodextrin with guest molecules as studied by electrospray mass spectrometry. Rapid Commun. Mass Spectrom., 8, 423-426 (1994).
16. Prokai, L., Ramanathan, R., Nawrocki, J., and Eyler, J., Electrospray ionization mass spectrometry of cyclodextrin complexes of amino acids and peptides. J. Inclusion Phenom. Mol. Recog. Chem., 25, 117-120 (1996).
17. Ramirez, J., He, F., and Lebrilla, C. B., Gas-phase chiral differentiation of amino acid guests in cyclodextrin hosts. J. Am. Chem. Soc., 120, 7387-7388 (1998).
18. Sun, W., Cui, M., Liu, S., Song, F., and Elkin, Y. N., Electrospray ionization mass spectrometry of cyclodextrin complexes with amino acids in incubated solutions and in eluates of gel permeation chromatography. Rapid Commun. Mass Spectrom., 12, 2016-2022 (1998).
19. Ramanathan, R., and Prokai, L., Electrospray ionization mass spectrometric study of encapsulation of amino acids by cyclodextrins. J. Am. Soc. Mass Spectrom., 6, 866-871 (1995).
20. Camilleri, P., Haskins, N. J., New, A. P., and Saunders, M. R., Analyzing the complexation of amino acids and peptides with β-cyclodextrin using electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom., 7, 949-952 (1993).
21. 1H NHR. J. Pharm. Biomed. Anal., 29, 487-494 (2002).
22. Selva, A., Redenti, E., Zanol, M., Ventura, P., and Casetta, B., Support for the proposed observation by ionspray mass spectrometry of piroxicam/β-cyclodextrin and terfenadine/β-cyclodextrin non-covalent inclusion complexes. Eur. Mass Spectrom., 1, 105-106 (1995).
23. Lu, W., and Cole, R. B., Determination of chiral pharmaceutical compounds, terbutaline, ketamine and propranolol, by on-line capillary electrophoresis-electrospray ionization mass spectrometry. J. Chromatogr. B, 714, 69-75 (1998).
24. Srinivasan, K., and Bartlett, M. G., Comparison of cyclodextrin- barbiturate noncovalent complexes using electrospray ionization mass spectrometry and capillary electrophoresis. Rapid Commun. Mass Spectrom., 14, 624-632 (2000).
25. Kobetic, R., Jursic, B. S., Bonnette, S., Tsai, J. S. C., and Salvatore, S. J., Study of the lorazepam:cyclodextrin inclusion complexes using electrospray ionization mass spectrometry. Tetrahedron Lett., 42, 6077-6082 (2001).
26. Al-nouti, Y., and Bartlett, M. G., Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom., 13, 928-935 (2002).
27. Smith, R. D., and Light-Wahl, K. J., The observation of non-covalent interactions in solution by electrospray ionization mass spectrometry: promise, pitfalls and prognosis. Biol. Mass Spectrom., 22, 493-501 (1993).
28. Cunniff, J. B., and Vouros, P., False positives and the detection of cyclodextrin inclusion complexes by electrospray mass spectrometry. J. Am. Soc. Mass Spectrom., 6, 437-447 (1995).
29. Package insert for Prostarmon™ E tablet, Ono pharmaceutical Co., Ltd., September 2003.
30. Koizumi, K., Mitsui, K., and Higuchi, K., Comparison between interactions of α- and β-cyclodextrin with barbituric acid derivatives. Yakugaku Zasshi (in Japanese), 94, 1515-1519 (1974).
31. Tanimoto, T., Kishimoto, Y., Ikuta, A., Nishi, Y., and Miyake, K., Preparation and characterization of branched β-cyclodextrins having mannno-oligosaccharide side chains derived from yeast mannan and study of their functions. J. Inclusion Phenom. Macrocyclic Chem., 44, 297-302 (2002).
32. Tanimoto, T., Omatsu, M., Ikuta, A., Nishi, Y., Murakami, H., Nakano, H., and Kitahata, S., Synthesis of novel heterobranched β-cyclodextrins having β-D-N-acetylglucosaminyl-maltotriose on the side chain. Biosci. Biotechnol. Biochem., 69, 732-739 (2005).
33. n-di-O-(L-fucopyranosyl)- β-cyclodextrin (n = II-IV) and investigation of their functions. Carbohydr. Res., 342, 2173-2181 (2007).