메뉴 건너뛰기




Volumn 9, Issue 3, 2003, Pages 784-792

Recognition of caffeine in aqueous solutions

Author keywords

Caffeine; Noncovalent interactions; Porphyrinoids; Sensors; Water chemistry

Indexed keywords

COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; SUBSTRATES;

EID: 0037416024     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390088     Document Type: Article
Times cited : (45)

References (57)
  • 2
    • 0040735624 scopus 로고    scopus 로고
    • S. R. Waldvogel, R. Fröhlich, C. A. Schalley, Angew. Chem. 2000, 112, 2580-2583; Angew. Chem. Int. Ed. 2000, 39, 2472-2475.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2472-2475
  • 15
    • 0011888714 scopus 로고    scopus 로고
    • For recent reviews about porphyrin receptors see: a) J. Weiss, J. Incl. Phenom. Macrocyclic Chem. 2001, 40, 1-22; b) A. Robertson, S. Shinkai, Coord. Chem. Rev. 2000, 205, 157-199; c) H. Ogoshi, T. Mizutani, Curr. Opin. Chem. Biol. 1999, 3, 736-739; d) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89.
    • (2001) J. Incl. Phenom. Macrocyclic Chem. , vol.40 , pp. 1-22
    • Weiss, J.1
  • 16
    • 0033830413 scopus 로고    scopus 로고
    • For recent reviews about porphyrin receptors see: a) J. Weiss, J. Incl. Phenom. Macrocyclic Chem. 2001, 40, 1-22; b) A. Robertson, S. Shinkai, Coord. Chem. Rev. 2000, 205, 157-199; c) H. Ogoshi, T. Mizutani, Curr. Opin. Chem. Biol. 1999, 3, 736-739; d) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89.
    • (2000) Coord. Chem. Rev. , vol.205 , pp. 157-199
    • Robertson, A.1    Shinkai, S.2
  • 17
    • 0032704878 scopus 로고    scopus 로고
    • For recent reviews about porphyrin receptors see: a) J. Weiss, J. Incl. Phenom. Macrocyclic Chem. 2001, 40, 1-22; b) A. Robertson, S. Shinkai, Coord. Chem. Rev. 2000, 205, 157-199; c) H. Ogoshi, T. Mizutani, Curr. Opin. Chem. Biol. 1999, 3, 736-739; d) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 736-739
    • Ogoshi, H.1    Mizutani, T.2
  • 18
    • 0002678891 scopus 로고    scopus 로고
    • For recent reviews about porphyrin receptors see: a) J. Weiss, J. Incl. Phenom. Macrocyclic Chem. 2001, 40, 1-22; b) A. Robertson, S. Shinkai, Coord. Chem. Rev. 2000, 205, 157-199; c) H. Ogoshi, T. Mizutani, Curr. Opin. Chem. Biol. 1999, 3, 736-739; d) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 81-89
    • Ogoshi, H.1    Mizutani, T.2
  • 19
    • 0036501398 scopus 로고    scopus 로고
    • For other water-soluble receptors based on cationic (N-alkyl)pyridyl porphyrins see: a) M. Sirish, V. A. Chertkov, H.-J. Schneider, Chem. Eur. J. 2002, 5, 1181-1188; b) H.-J. Schneider, L. Tianjun, M. Sirish, V. Malinovski, Tetrahedron 2002, 58, 779-786; c) M. Sirish, H.-J. Schneider, J. Am. Chem. Soc. 2000, 122, 5881-5882.
    • (2002) Chem. Eur. J. , vol.5 , pp. 1181-1188
    • Sirish, M.1    Chertkov, V.A.2    Schneider, H.-J.3
  • 20
    • 0037147978 scopus 로고    scopus 로고
    • For other water-soluble receptors based on cationic (N-alkyl)pyridyl porphyrins see: a) M. Sirish, V. A. Chertkov, H.-J. Schneider, Chem. Eur. J. 2002, 5, 1181-1188; b) H.-J. Schneider, L. Tianjun, M. Sirish, V. Malinovski, Tetrahedron 2002, 58, 779-786; c) M. Sirish, H.-J. Schneider, J. Am. Chem. Soc. 2000, 122, 5881-5882.
    • (2002) Tetrahedron , vol.58 , pp. 779-786
    • Schneider, H.-J.1    Tianjun, L.2    Sirish, M.3    Malinovski, V.4
  • 21
    • 0034697641 scopus 로고    scopus 로고
    • For other water-soluble receptors based on cationic (N-alkyl)pyridyl porphyrins see: a) M. Sirish, V. A. Chertkov, H.-J. Schneider, Chem. Eur. J. 2002, 5, 1181-1188; b) H.-J. Schneider, L. Tianjun, M. Sirish, V. Malinovski, Tetrahedron 2002, 58, 779-786; c) M. Sirish, H.-J. Schneider, J. Am. Chem. Soc. 2000, 122, 5881-5882.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5881-5882
    • Sirish, M.1    Schneider, H.-J.2
  • 23
    • 0001688882 scopus 로고    scopus 로고
    • A statistical mixture of atropoisomers is expected to be present in solution. In this case the αααβ isomer, the most abundant one, together with the αααα isomer should account for 62.5% of the mixture. NMR measurements did not provide any indications about isomer distribution. Changes seem to occur induced by complexation but are also difficult to be quantified, see T. Mizutani, T. Horiguchi, H. Koyama, I. Uratani, H. Ogoshi, Bull. Chem. Soc. Jpn. 1998, 71, 413-418.
    • (1998) Bull. Chem. Soc. Jpn. , vol.71 , pp. 413-418
    • Mizutani, T.1    Horiguchi, T.2    Koyama, H.3    Uratani, I.4    Ogoshi, H.5
  • 24
    • 0035065777 scopus 로고    scopus 로고
    • A basic buffer was chosen to allow comparison of the data obtained for caffeine with that obtained for more basic guests (Tables 4 and 5) without having to consider protonation equilibria (see, M. V. Rekharsky, A. Nakamura, G. A. Hembury, Y. Inoue, Bull. Chem. Soc. Jpn. 2001, 74, 449-457). Furthermore, as shown for receptor Zn-1f in Table 1, there is not any appreciable effect on caffeine binding if the acidic oxalate buffer is used (with the exception of Zn-1c due to the ionization equilibrium involving the Tyr OH group).
    • (2001) Bull. Chem. Soc. Jpn. , vol.74 , pp. 449-457
    • Rekharsky, M.V.1    Nakamura, A.2    Hembury, G.A.3    Inoue, Y.4
  • 27
    • 84986379497 scopus 로고
    • -1) and, therefore, do not affect the binding process in our experiments, see reference [4] and I. Horman, B. Dreux, Helv. Chim. Acta 1984, 67, 754-764.
    • (1984) Helv. Chim. Acta , vol.67 , pp. 754-764
    • Horman, I.1    Dreux, B.2
  • 28
    • 0242412943 scopus 로고    scopus 로고
    • note
    • -3M). Aggregation was also not observed in these conditions as proven directly by a microcalorimetric experiment on porphyrin Zn-1e (see experimental section).
  • 30
    • 0242412944 scopus 로고    scopus 로고
    • See reference [14a], and references therein
    • See reference [14a], and references therein.
  • 32
    • 0242496219 scopus 로고    scopus 로고
    • note
    • a obtained from measurements in different concentration ranges (UV and ITC) were in good agreement.
  • 33
    • 0242412942 scopus 로고    scopus 로고
    • note
    • For an example in which the occurrence of 2:1 complexes is considered see reference [36].
  • 34
    • 0242657587 scopus 로고    scopus 로고
    • T. Liu, H.-J. Schneider, Angew. Chem. 2002, 114, 1418-1420; Angew. Chem. Int. Ed. 2002, 41, 1368-1370.
    • (2002) Angew. Chem. , vol.114 , pp. 1418-1420
    • Liu, T.1    Schneider, H.-J.2
  • 35
    • 0037091014 scopus 로고    scopus 로고
    • T. Liu, H.-J. Schneider, Angew. Chem. 2002, 114, 1418-1420; Angew. Chem. Int. Ed. 2002, 41, 1368-1370.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1368-1370
  • 41
    • 0242580659 scopus 로고    scopus 로고
    • note
    • The signals have a complex multiplicity pattern, which agrees with the presence in solution of different conformational isomers interconverting slowly on the NMR chemical shift timescale at room temperature.
  • 43
    • 0242412940 scopus 로고    scopus 로고
    • note
    • This is not surprising since ITC measurements performed at concentrations 500-1000 times higher than UV measurements present a higher contribution coming from the existence of 2:1 species.
  • 45
    • 37049111701 scopus 로고
    • The two caffeine molecules are found declined asymmetrically between the two dirhodium-diacetate planes in order to accommodate base stacking, see K. Aoki, H. Yamazaki, J. Chem. Soc. Chem. Commun. 1980, 186-188.
    • (1980) J. Chem. Soc. Chem. Commun. , pp. 186-188
    • Aoki, K.1    Yamazaki, H.2
  • 50
    • 0001576555 scopus 로고
    • Stacking interactions between the Tyr phenol moiety and tetracationic 5,10,15,20-tetrakis-(N-methylpyridinium-4-yl)porphyrinato zinc(II) chloride salt give stabilization to the porphyrin-Tyr complex in aqueous solutions, see: a) E. Mikros, A. Gaudamer, R. Pasternack, Inorg. Chim. Acta 1988, 153, 199-200; b) C. Verchére-Bèaur, E. Mikros, M. Perrée-Fauvet, A. Gaudamer, J. Inorg. Biochem. 1990, 40, 127-139.
    • (1988) Inorg. Chim. Acta , vol.153 , pp. 199-200
    • Mikros, E.1    Gaudamer, A.2    Pasternack, R.3
  • 51
    • 0025036476 scopus 로고
    • Stacking interactions between the Tyr phenol moiety and tetracationic 5,10,15,20-tetrakis-(N-methylpyridinium-4-yl)porphyrinato zinc(II) chloride salt give stabilization to the porphyrin-Tyr complex in aqueous solutions, see: a) E. Mikros, A. Gaudamer, R. Pasternack, Inorg. Chim. Acta 1988, 153, 199-200; b) C. Verchére-Bèaur, E. Mikros, M. Perrée-Fauvet, A. Gaudamer, J. Inorg. Biochem. 1990, 40, 127-139.
    • (1990) J. Inorg. Biochem. , vol.40 , pp. 127-139
    • Verchére-Bèaur, C.1    Mikros, E.2    Perrée-Fauvet, M.3    Gaudamer, A.4
  • 52
    • 0242664634 scopus 로고    scopus 로고
    • note
    • The difference observed between Zn-1c and metal-free 1c is δ = 0.1.
  • 53
    • 4244064293 scopus 로고
    • th ed., CRC, Cleveland, Ohio, 1977, p. C-767. No mention is made about the ionic strength under which this value was measured.
    • (1977) th Ed.
  • 54
    • 0000856541 scopus 로고
    • Similar intramolecular coordination has been shown for pyridyl-appended Zn-tetraphenyl porphyrins in nonpolar solvents: F. A. Walker, M. Benson, J. Am. Chem. Soc. 1980, 102, 5530-5538.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5530-5538
    • Walker, F.A.1    Benson, M.2
  • 55
    • 0242664633 scopus 로고    scopus 로고
    • note
    • From electronic considerations, imidazole and 1-methylimidazole should be better ligands than caffeine, as they more basic.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.