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Properties of B‐ring analogues of colchicine
Author(s) -
Maity Sankar N.,
Bhattacharyya B.
Publication year - 1987
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(87)81027-x
Subject(s) - tropone , colchicine , ring (chemistry) , chemistry , substituent , stereochemistry , absorption (acoustics) , chromophore , photochemistry , organic chemistry , biology , physics , genetics , acoustics
Absorption spectra of colchicine and its analogues are affected by the presence of the B‐ring, although it is not part of the chromophore (C‐ring). Thus, 2‐methoxy‐5‐(2′,3′4′‐trimethoxyphenyl)tropone has absorption maxima at 341 nm, whereas that of desacetamidocolchicine is at 353 nm. A similar red shift in the λ max of colchicine, desacetamidocolchicine and 2‐methoxy‐(2′,3′,4′‐trimethoxyphenyl)tropone also occurs when they are immobilized in the binding site to tubulin or in pure glycerol. We also observed that the B‐ring of colchicine alone or with substituent does not affect the UV‐induced rearrangement of colchicine to lumicolchicine. However, in the absence of the B‐ring, as in the case of 2‐methoxy‐5‐(2′,3′4′‐trimethoxyphenyl)tropone, the rearrangement reaction of the C‐ring slows down significantly.