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Volumn 61, Issue 45, 2005, Pages 10689-10698

Steroid-based head-to-tail amphiphiles as effective iono- and protonophores

Author keywords

Amphiphile; Ionophore; Protonophore; Steroids

Indexed keywords

3BETA [(TERT BUTYLDIPHENYLSILYL)OXY] 5ALPHA 23,24 BISNORCHOL 16 EN 6ALPHA,7BETA,22 TRIOL; AMPHOPHILE; AMPHOTERICIN B; BENZENE DERIVATIVE; EPIANDROSTERONE; ETHYLENE DERIVATIVE; IONOPHORE; POLYENE ANTIBIOTIC AGENT; POLYETHER ANTIBIOTIC AGENT; PROTON; SODIUM ION; STEROID; UNCLASSIFIED DRUG;

EID: 26244436645     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.085     Document Type: Article
Times cited : (10)

References (26)
  • 12
    • 26244441223 scopus 로고    scopus 로고
    • note
    • A case in which the polar head (the oligo(ethyleneglycol) moiety), matches the length of the lipophilic part (the sterol nucleus).
  • 13
    • 26244464136 scopus 로고    scopus 로고
    • note
    • Molecular mechanic calculations (MM3) were performed in order to optimize the geometries of the 'folded' and the 'extended' conformations of 2.
  • 14
    • 0029790201 scopus 로고    scopus 로고
    • This is generally believed to be the active conformation of the poly(ethyleneglycol) derivative (see: E. Stadler, P. Dedek, K. Yamashita, and S.L. Regen J. Am. Chem. Soc. 118 1996 8975 8976 ). It is worth noting that on note 23 of the paper from Stadler et al., no ionophoric activity was found for 5-androsten-3β-(oxycarbonyl)-hexa(ethylenglycol) (31, 2% mol in egg PC vesicles) over a 20 h period. It is easy to recognize how 31 is similar to our conjugates 1-5
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8975-8976
    • Stadler, E.1    Dedek, P.2    Yamashita, K.3    Regen, S.L.4
  • 15
    • 26244447017 scopus 로고    scopus 로고
    • note
    • It must be noted that for 'complex minimalist systems' (see Ref. 6), such as those represented by monomeric steroids, this kind of structurally simple self-assembly motif (never proposed before), can be equally probable.
  • 16
    • 26244446879 scopus 로고    scopus 로고
    • note
    • + signal, as a function of time, yields the kinetic profiles.
  • 22
    • 0019883199 scopus 로고
    • The protonophoric activities were measured using an assay based on the response of the intravesicular pH-sensitive pyranine fluorophore. See: N.R. Clement, and J.M. Gould Biochemistry 20 1981 1534 1538
    • (1981) Biochemistry , vol.20 , pp. 1534-1538
    • Clement, N.R.1    Gould, J.M.2
  • 23
    • 26244464518 scopus 로고    scopus 로고
    • note
    • -1.
  • 25
    • 0041843738 scopus 로고    scopus 로고
    • Theoretical studies showed that the size and polarity of the inner channel influences proton transport acting on the degree of proton solvatation. See: Y. Wu, and G. Voth Biophys. J. 85 2003 864 875
    • (2003) Biophys. J. , vol.85 , pp. 864-875
    • Wu, Y.1    Voth, G.2
  • 26
    • 0001229636 scopus 로고
    • It is well known that in most of the membrane-active saponins and steroidal oligoglycosides the polar sugars are linked at C-3 and/or C-6. See: M.V. D'Auria, L. Minale, and R. Riccio Chem. Rev. 93 1993 1839 1895
    • (1993) Chem. Rev. , vol.93 , pp. 1839-1895
    • D'Auria, M.V.1    Minale, L.2    Riccio, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.