Complexation and (templated) synthesis of rhenium complexes with cyclodextrins and cyclodextrin dimers in water

Chemistry - A European Journal

Volumn 7, Issue 16, 2001, Pages 3603-3615

  Van Bommel, Kjeld J C ^a,b   De Jong, Menno R ^a   Metselaar, Gerald A ^a   Verboom, Willem ^a   Huskens, Jurriaan ^a   Hulst, Ron ^c   Kooijman, Huub ^d   Spek, Anthony L ^d   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b NUCLEAR RESEARCH AND CONSULTANCY GROUP NRG   (Netherlands)

^c UNIVERSITY OF TWENTE   (Netherlands)

^d UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Cyclodextrins; Radiopharmaceuticals; Rhenium; Supramolecular chemistry; Templated synthesis

Indexed keywords

DIMERS; SYNTHESIS (CHEMICAL); WATER;

BIOMOLECULES;

RHENIUM COMPOUNDS;

CYCLODEXTRIN DERIVATIVE; DIMER; RHENIUM COMPLEX;

ARTICLE; COMPLEX FORMATION; ISOTOPE LABELING; MOLECULAR INTERACTION; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CYCLODEXTRINS; DIMERIZATION; INDICATORS AND REAGENTS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; RHENIUM; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; WATER;

EID: 0035902896     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010817)7:16<3603::AID-CHEM3603>3.0.CO;2-E     Document Type: Article

References (76)

1. For recent reviews of medicinal inorganic chemistry in general, or (rhenium) radiopharmaceuticals in specific see: a) Chem. Rev. 1999, 99, Issue 9;
2. b) Z. Guo, P. J. Sadler, Angew. Chem. 1999, 111, 1610-1630;
3. Angew. Chem. Int. Ed. 1999, 38, 1513-1531;
4. c) K. Schwochau, Angew. Chem. 1994, 106, 2349-2358;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 2258-2267;
6. d) J. R. Dilworth, S. J. Parrot, Chem. Soc. Rev. 1998, 27, 43-55.
7. For reviews on CD chemistry see Chem. Rev. 1998, 98, Issue 5.
8. J. Szejtli, Med. Res. Rev. 1994, 14, 353-386.
9. K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045-2076.
10. S. D. Eastburn, B. Y. Tao, Biotech. Adv. 1994, 12, 325-339.
11. β-CD dimer complexes with potential applications in photodynamic therapy have been reported: a) J. G. Moser, A. Ruebner, A. Vervoorts, B. Wagner, J. Incl. Phenom. Macromol. Chem. 1996, 25, 29-34;
12. b) A. Ruebner, J. G. Moser, D. Kirsch, B. Spengler, S. Andrees, S. Roehrs, J. Incl. Phenom. Macromol. Chem. 1996, 25, 35-38;
13. c) A. Ruebner, D. Kirsch, S. Andrees, W. Decker, B. Roeder, B. Spengler, R. Kaufmann, J. G. Moser, J. Incl. Phenom. Macromol. Chem. 1997, 27, 69-84;
14. d) A. Ruebner, Z. Yang, D. Leung, R. Breslow, Proc. Natl. Acad. Sci. USA 1999, 96, 14692-14693.
15. F. Hirayama, K. Uekama, Adv. Drug Delivery Rev. 1999, 36, 125-141.
16. K. H. Frömming, J. Szejtli, Cyclodextrins in Pharmacy, Kluwer Academic Publisher, Dordrecht, 1993, p. 324.
17. J. Szejtli, Cyclodextrin Technology, Kluwer Academic Publisher, Dordrecht, 1988, p. 450.
18. G. N. Kalinkova, Int. J. Pharm. 1999, 187, 1-15.
19. D. W. Oliver, I. C. Dormehl, W. Louw, E. Kilian, V. de Beco, J. L. Morretti, Arzneimittel Forsch. 2000, 50, 758-764.
20. C. Bolzati, A. Boschi, L. Uccelli, A. Duatti, R. Franceschini, A. Piffanelli, Nucl. Med. Biol. 2000, 27, 309-314.
21. K. Takahashi, Chem. Rev. 1998, 98, 2013-2033.
22. 2+ complexing with the methanol present.
23. K. J. C. van Bommel, W. Verboom, R. Hulst, H. Kooijman, A. L. Spek, D. N. Reinhoudt, Inorg. Chem. 2000, 39, 4099-4206.
24. M. R. de Jong, J. F. J. Engbersen, J. Huskens, D. N. Reinhoudt, Chem. Eur. J. 2000, 6, 4034-4040.
25. 2, and the free and bound shift values, using a spreadsheet methodology developed before: J. Huskens, H. van Bekkum, J. A. Peters, Comp. Chem. 1995, 19, 409-416.
26. K. A. Connors, J. Pharm. Sci. 1995, 84, 843-848.
27. K. A. Connors, Binding constants, the measurement of molecular complex stability, Wiley, New York, 1987, Chapter 4.
28. 2benz.
29. CPK molecular models suggest that only one of the two aromatic rings can be complexed at any given time, due to the distance between the β-CD moieties. NMR spectra indicate that there is a rapid exchange between the extremes, that is, either one of the aromatic rings inside a β-CD cavity.
30. obs values is estimated to be ±0.3.
31. K. A. Connors, M. J. Mulski, A. Paulson, J. Org. Chem. 1992, 57, 1794-1798.
32. 1, the reported value of 4.9 could be used for the fitting procedure.)
33. 2dans 14 is 10.3±1.0.
34. For the different aspects of rhenium radiopharmaceuticals see the review of Dilworth and Parrot, ref. [1d].
35. B. Johannsen, R. Syhre, Radiochem. Radioanal. Lett. 1978, 36, 107-110.
36. B. Noll, T. Kniess, M. Freibe, H. Spies, B. Johannsen, Isotopes Environ. Health Stud. 1996, 32, 21-29.
37. 4.
38. +) to facilitate extraction of the formed complexes to the organic layer.
39. 1H NMR signals belonging to compound cis-11a are listed in the Experimental Section.
40. Due to the degree of symmetry present in both the cis as well as the trans complex, the structure of the two complexes could not be proven with NMR.
41. Only one example of preferential product formation using a CD-dimer has been reported, however, without stereoselectivity: C. J. Easton, J. B. Harper, S. F. Lincoln, New J. Chem. 1998, 1163-1165.
42. a) D. H. Busch, A. L. Vance, A. G. Kolchinkski, in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J.-P. Sauvage, M. W. Hosseini), Elsevier, Amsterdam/New York, 1996, p. 1;
43. b) R. G. Chapman, J. C. Sherman, Tetrahedron 1997, 53, 15911-15945.
44. D. Y. Chi, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1993, 115, 7045-7046.
45. R. K. Hom, D. Y. Chi, J. A. Katzenellenbogen, J. Org. Chem. 1996, 61, 2624-2631.
46. The other bis(bidentate) complexes were not isolated.
47. Besides the three bis(bidentate) complexes, TLC showed several other spots belonging to compounds which were not identified.
48. Although actual complexation of the pyridine ligand by β-CD has not been established here, pyridine derivatives are known to form inclusion complexes with β-CD: a) I. Satake, S. Yoshida, K. Hayakawa, T. Maeda, Y. Kusumoto, Bull. Chem. Soc. Jpn. 1986, 59, 3991-3993;
49. b) M. Cotta Ramusino, L. Rufini, C. Mustazza, J. Inclusion Phenom. Mol. Recogn. 1993, 15, 359-368.
50. 3O, making purification somewhat troublesome.
51. a) F. Djedaïni-Pilard, J. Désalos, B. Perly, Tetrahedron Lett. 1993, 34, 2457-2460;
52. b) M. K. Hristova-Kazermieski, P. Horan, P. Davis, H. I. Yamamura, T. Kramer, R. Horvath, W. M. Kazermieski, F. Porreca, V. J. Hruby, Bioorg. Med. Chem. Lett. 1993, 3, 831-834;
53. c) N. Schaske, S. Fiori, E. Weyher, C. Escrieut, D. Fourmy, G. Müller, L. Moroder, J. Am. Chem. Soc. 1998, 120, 7030-7038.
54. a) N. Schaske, I. Assfalg-Machleidt, W. Machleidt, T. Lassleben, C. P. Sommerhoff, L. Moroder, Biorg. Med. Chem. Lett. 2000, 10, 677-680;
55. b) C. Péan, C. Créminon, A. Wijkhuisen, J. Grassi, P. Guenot, P. Jéhan, J.-P. Dalbiez, B. Perly, F. Djedaïni-Pilard, J. Chem. Soc. Perkin Trans. 2 2000, 853-863.
56. S. Liu, S. Edwards, Chem. Rev. 1999, 99, 2235-2268.
57. J. M. Peeters, T. G. Hazendonk, E. C. Beuvery, G. I. Tesser, J. Immunol. Methods 1989, 120, 133-143.
58. R. J. S. Duncan, P. D. Weston, R. Wrigglesworth, Anal. Biochem. 1983, 132, 68-73.
59. A. Bax, R. Freeman, J. Magn. Reson. 1981, 44, 542-546.
60. A. Bax, D. G. Davis, J. Magn. Reson. 1985, 65, 355-60.
61. J. Jeener, B. M. Meier, P. Bachmann, R. R. Ernst, J. Chem. Phys. 1979, 71, 4546-4553.
62. A. Bax, R. H. Griffey, B. L. Hawkins, J. Magn. Reson. 1983, 55, 301-315.
63. D. J. States, R. A. Haberkorn, D. J. Ruben, J. Magn. Reson. 1982, 48, 286-292.
64. M. Karas, D. Bachmann, U. Bahr, F. Hillenkamp, Int. J. Mass Spectrom. Ion Processes 1987, 78, 53-68.
65. F. Hillenkamp, M. Karas, Anal. Chem. 1991, 63, A1193-A1202.
66. K. Tanaka, H. Waki, Y. Ido, S. Akita, Y. Yoshida, T. Yoshida, Rapid Commun. Mass Spectrom. 1988, 2, 151-153.
67. M. L. Vestal, P. Juhasz, S. A. Martin, Rapid Commun. Mass Spectrom. 1995, 9, 1044-1050.
68. H.-F. Grützmacher, W. Husemann, Tetrahedron 1987, 43, 3205-3212.
69. E. van Dienst, B. H. M. Snellink, I. Von Piekartz, M. H. B. Grote Gansey, F. Venema, M. C. Feiters, R. J. M. Nolte, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1995, 60, 6537-6545.
70. Compound 2 has been described in patents only: Ciba-Geigy, DE 2749902 [Chem. Abstr. 1978, 89, 112428].
71. J. K. Chakrabarti, M. J. Foulis, S. S. Szinai, Tetrahedron Lett. 1968, 6249-6252.
72. This compound was synthesized before, however, using pyridin-2-yl-methanol and thioacetic acid: ref. [60].
73. Synthesized according to an adapted literature procedure: R. Deziel, E. Malenfant, Bioorg. Med. Chem. Lett. 1998, 8, 1437-1442.
74. A. L. Spek, PLATON - A multi-purpose crystallographic tool, Utrecht University, The Netherlands, 1999; Internet: http://www. cryst.chem.uu.nl/platon.
75. G. M. Sheldrick, SHELXL-97: Program for crystal structure refinement, University of Göttingen, Germany, 1997.
76. G. M. Sheldrick, SHELXS86: Program for crystal structure determination, University of Göttingen, Germany, 1986.