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Volumn 126, Issue 10, 2004, Pages 3185-3190

Synthetic Creatinine Receptor: Imprinting of a Lewis Acidic Zinc(II)cyclen Binding Site to Shape Its Molecular Recognition Selectivity

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE; MOLECULAR STRUCTURE; PH EFFECTS; POLYMERIZATION; SOLUTIONS;

EID: 1642339624     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038980l     Document Type: Article
Times cited : (79)

References (61)
  • 1
  • 8
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    • (a) Wulff, G. Angew. Chem. 1995, 107, 1958-1979; Angew. Chem., Int. Ed. 1995, 34, 1812-1833.
    • (1995) Angew. Chem. , vol.107 , pp. 1958-1979
    • Wulff, G.1
  • 9
    • 0028873867 scopus 로고
    • (a) Wulff, G. Angew. Chem. 1995, 107, 1958-1979; Angew. Chem., Int. Ed. 1995, 34, 1812-1833.
    • (1995) Angew. Chem. Int. Ed. , vol.34 , pp. 1812-1833
  • 16
    • 0002370868 scopus 로고    scopus 로고
    • ACS Symposium Series 703; Bartsch, R. A., Maeda, M., Eds.; American Chemical Society: Washington, DC
    • (f) Arnold, F. In Molecular and lonic Recognition with Imprinted Polymers; ACS Symposium Series 703; Bartsch, R. A., Maeda, M., Eds.; American Chemical Society: Washington, DC, 1998; p 109.
    • (1998) Molecular and Lonic Recognition with Imprinted Polymers , pp. 109
    • Arnold, F.1
  • 35
  • 36
    • 0038779382 scopus 로고    scopus 로고
    • A water-soluble polymer bound iron porphyrin as cytochrome c oxidase model was recently reported by Collman et al. No imprinting template was used in this work. Collman, J. P.; Fudickar, W.; Shiryaeva, I. Inorg. Chem. 2003, 42, 3384-3386.
    • (2003) Inorg. Chem. , vol.42 , pp. 3384-3386
    • Fudickar, W.1    Shiryaeva, I.2
  • 37
    • 0001405801 scopus 로고    scopus 로고
    • For a study aiming to identify carbohydrate-metal complex interactions, which may be used for imprinting processes, see: Striegler, S.; Tewes, E. Eur. J. Inorg. Chem. 2002, 487-495.
    • (2002) Eur. J. Inorg. Chem. , pp. 487-495
    • Striegler, S.1    Tewes, E.2
  • 46
  • 47
    • 1642314557 scopus 로고    scopus 로고
    • note
    • Comparison of the regioisomer ratio of meta and para in 4 and in product 5 shows that this has slightly changed. One of the isomers seems to be more reactive in the substitution reaction. Overlap of signals in the NMR spectra of 5 does not allow the determination of the exact regioisomer ratio.
  • 48
    • 1642332293 scopus 로고    scopus 로고
    • note
    • (a) The tetraacetyl derivative of riboflavin is used because of its higher photostability and better solubility properties compared to riboflavin.
  • 50
    • 1642285144 scopus 로고    scopus 로고
    • note
    • Creatinine is an important analyte in medicinal diagnostics. The amount of excreted creatinine determines the globular filtration rate of a body. The value should be in a specific range for healthy humans, and it is used as a medical indicator. Determination of creatinine levels in medicinal diagnostics is performed by a photometric assay that requires three enzymes. The assay is highly selective and sensitive, but it is expensive due to the sensitivity of the enzymes to degredation.
  • 54
    • 1642270643 scopus 로고    scopus 로고
    • note
    • If nitrogen atoms from other sources, e.g., the radical initiator, are incorporated into the polymer during preparation, the theoretical maximum number of binding sites would be smaller than calculated. The more important value of accessible binding sites was determined from binding isotherms.
  • 55
    • 1642312915 scopus 로고    scopus 로고
    • note
    • The sensitivity of the metal complex monomer incorporation rate to the reaction conditions is illustrated with polymers 11-Zn-8-A and -B. By a slight increase of the amount of cross-linker (EDGMA + 13%) and the use of more solvent for polymerization, the rate of metal complex incorporation decreases from 50% (11-Zn-8-A) to 26% (11-Zn-8-B). The rate of incorporation seems to be concentration dependent, yielding higher rates of incorporation at higher concentrations, but the poor solubility of 6-Zn-7 does not allow increasing its concentration further. Another possible rationale for the observed incomplete incorporation may come from the metal complex monomer structure, which bears two flexible vinyl units. During polymerization an intramolecular reaction followed by radical transfer may happen, which will exclude the monomer from incorporation into the polymer matrix. Collman et al. recently described the copolymerization of vinyl Fe-porphyrins; see ref 9. While a porphyrin monomer with one polymerizable group was incorporated in more than 90%, a second monomer with three flexible vinyl groups was embedded into the polymer in only ∼60%. Functional monomers used for other MIP preparation have one polymerizable unit or two geometrically well-separated groups (see refs 3m, 3n, and 8).
  • 56
    • 1642351847 scopus 로고    scopus 로고
    • note
    • This value exceeds reported numbers of accessible binding sites of respectively 20% 6 and 7-10%.7
  • 60
    • 1642403706 scopus 로고    scopus 로고
    • note
    • An additional argument for this hypothesis comes from the fit of the binding isotherm to a one set of sites model, which fails to describe MIP in many cases.
  • 61
    • 1642363266 scopus 로고    scopus 로고
    • note
    • Binding of creatinine to polymer 11-Zn is very weak. Therefore, the ratio of binding affinities which is derived from polymer binding experiments must have a much larger error than the ratio derived from two solution studies.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.