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Volumn 47, Issue 29, 2008, Pages 5398-5401

Activation and stabilization of drugs by supramolecular pKa shifts: Drug-delivery applications tailored for cucurbiturils

Author keywords

Cucurbiturils; Host guest systems; Prodrugs; Proton pump inhibitors; Protonation

Indexed keywords

ACIDS; HYDROCHLORIC ACID; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS;

EID: 49149093365     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801054     Document Type: Article
Times cited : (248)

References (35)
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    • (2000) Clin. Ther , vol.22 , pp. 266-280
    • Horn, J.1
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    • 23744480691 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4844-4870.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4844-4870
  • 25
    • 53549094768 scopus 로고    scopus 로고
    • All kinetic measurements were performed at pH 2.9, at which decomposition in the absence CB7 is sufficiently slow to be accurately followed; at higher pH values, the active form is inefficiently formed, while at lower, more acidic, pH values, decomposition is too fast (seconds) to be accurately measured by conventional methods; see Ref. [13].
    • All kinetic measurements were performed at pH 2.9, at which decomposition in the absence CB7 is sufficiently slow to be accurately followed; at higher pH values, the active form is inefficiently formed, while at lower, more acidic, pH values, decomposition is too fast (seconds) to be accurately measured by conventional methods; see Ref. [13].
  • 26
    • 53549130787 scopus 로고    scopus 로고
    • The activation rate (determined by UV spectroscopy) was independent, within error, of the CB7 concentration (50 μM 1a, 0.1-4 mM CB7), which suggests that the complexation by the macrocycle is not the rate-determining step in the formation of the active form, but is instead the reaction of 1 to 2 inside the complex.
    • The activation rate (determined by UV spectroscopy) was independent, within error, of the CB7 concentration (50 μM 1a, 0.1-4 mM CB7), which suggests that the complexation by the macrocycle is not the rate-determining step in the formation of the active form, but is instead the reaction of 1 to 2 inside the complex.
  • 27
    • 53549084955 scopus 로고    scopus 로고
    • The actual catalytic effect on the initial nucleophilic substitution step (Scheme 1) may be larger, because the observed rate for the formation of the active species 2 in the presence of CB7 includes a dehydration step as a follow-up reaction.
    • The actual catalytic effect on the initial nucleophilic substitution step (Scheme 1) may be larger, because the observed rate for the formation of the active species 2 in the presence of CB7 includes a dehydration step as a follow-up reaction.
  • 28
    • 53549131339 scopus 로고    scopus 로고
    • At any given pH value, the ratio of the monoprotonated prototropic forms II/I is given as 10pKa,2-pKa,1
    • pKa,2-pKa,1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.