Harry Robbins


A series of anti, anti-dichloro-N-substituted azaadamantanes have been synthesized (Henkel et al, 1981, J. Org. Chem. , 46, 3483) representing conformationally rigid nitrogen mustards incorporated into an adamantyl framework with well defined stereochemistry and fixed separation distances between alkylating centers of 3.6 A (1) and 2.5 X (2,3) (Henkel et al, 1981, J. Org. Chem., 46, 3483) to be used as structurally rigid probes of DNA alkylation and intermolecular crosslink formation leading to cytotoxicity. The aqueous solution stability and the extent of intermolecular DNA crosslink formation for both the N-methyl and N-piperdinoethyl series of isomers have been measured using novel modifications of an ethidium bromide fluorescence assay technique. Results indicate that isomers 1 and 2 of both series form intermolecular crosslinks to an appreciable extent, while little or no crosslinking is observed under similar conditions for isomer 3 of both series. Analysis of the aqueous solution stability, time dependent crosslinking reaction isotherms and crosslink stability indicate significant differences both within and between series, which suggests stereospecific crosslinking behavior at the molecular level.

Library of Congress Subject Headings

Recombinant DNA--Analysis; DNA--Analysis; Nitrogen mustards; Genetic toxicology

Publication Date


Document Type


Department, Program, or Center

School of Chemistry and Materials Science (COS)


Takacs, Gerald

Advisor/Committee Member

Reinhardt, Christian


Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works. Physical copy available through RIT's The Wallace Library at: QH445.R62 1985


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