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Calicheamicin θ 1 I : A Rationally Designed Molecule with Extremely Potent and Selective DNA Cleaving Properties and Apoptosis Inducing Activity
Author(s) -
Nicolaou K. C.,
Li T.,
Nakada Masahisa,
Hummel Conrad W.,
Hiatt A.,
Wrasidlo W.
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199401831
Subject(s) - calicheamicin , diradical , dna , chemistry , ion , molecule , combinatorial chemistry , stereochemistry , biochemistry , biophysics , biology , organic chemistry , genetics , physics , nuclear physics , singlet state , antibody , excited state
The attack of a thiolate ion on the trisulfide unit of natural calicheamicin γ I 1( 1 ) activates it to form a diradical, which then attacks DNA. Thioacetate 2 is even more readily activated—under mildly basic conditions caused by OH ‐ ions—and likewise exhibits extremely interesting biological properties.