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Tritium labelling of antitumor DNA bis‐intercalators: Synthesis of [ 3 H] ditercalinium
Author(s) -
Léon P.,
GarbayJaureguiberry C.,
Le Greneur S.,
Besselièvre R.,
Roques B. P.
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580251012
Subject(s) - chemistry , carbazole , labelling , tritium , piperidine , stereochemistry , yield (engineering) , intercalation (chemistry) , chemical synthesis , dna , mechanism of action , dna synthesis , in vitro , organic chemistry , biochemistry , physics , materials science , nuclear physics , metallurgy
Ditercalinium : 2,2′‐[4,4′‐bipiperidine‐1,1′‐bis (ethane‐1,2‐diyl)] bis (1O‐methoxy‐7H‐pyrido[4,3‐c] carbazolium) tetramethanesulfonate (NSC 366241) is a potent antitumor DNA bis‐intercalator characterized by a new mechanism of action. In order to elucidate its biological action at the cellular level and its pharmacokinetic and metabolic properties, radiolabelled ditercalinium was prepared. In the present paper, we report the synthesis of the 11‐bromo‐1O‐methoxy‐7H‐pyrido [4,3‐c] carbazole presursor and its reductive tritiation by exchange with [ 3 H] 2 . The pyrido[4,3‐c]carbazole ring labelled in position 11 is then condensed either with the 1,1′ bis (2‐chloroethyl)‐ 4,4′‐bipiperidine chain to provide tritiated ditercalinium or with the 1‐(2‐chloroethyl) piperidine chain to yield its monomeric analog.