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Some chemical and biochemical studies relating to chemical carcinogens.

Russell, Jeremy Colin. (1984) Some chemical and biochemical studies relating to chemical carcinogens. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

This thesis is largely concerned with the study of a series of compounds, related to 15,16-dihydrocyclopenta-[a]-phenanthren-17-one, which have very specific structure-activity relationships. Chapter 1 deals with the general tritiation of a number of these compounds, where labelling patterns were analysed using 3H-nmr spectroscopy. Similar studies were also performed on a related series of poly-aromatic hydrocarbons. The results of the detritiation kinetics,in aqueous sodium hydroxide, of a number of [16-[3]H]-15,16-dihydrocyclopenta-[a]-phenanthren-17-ones and similar ketones are presented in chapter 2. The results allowed interpretation in terms of both inductive effects and the three-dimensional shape of the molecules. Comparative in vitro metabolism of a number of 15,16-dihydrocyclopenta-[a]-phenanthren-17-ones, reported in chapter 3, showed that all of the compounds produce a trans-3,4-dihydrodiol in similar amounts, with the exception of the 1-methyl isomer, which yielded a 4-phenol. The mere presence of such a diol was shown not to necessarily imply carcinogenic activity in the compound under study. In chapter 4 the results of an investigation of the binding to DNA in vivo and in vitro of a series of 15,16-dihydrocyclopenta-[a]-phenanthren-17-ones are given. Each gave similar adduct patterns, where the major product is that derived from a deoxyguanosine residue. The dose/binding ratio of the 11-methyl derivative shows a linear relationship over a 32-fold range of dose, whilst the excision of the adducts from the DNA of the 12-methyl isomer is at a rate faster than that of cell division. The final chapter is concerned with the tritiation of a number of nitro and amino aromatic compounds, of interest in cancer chemistry. This was done either by direct catalytic exchange or by introducing the isotope as part of a synthetic step. The [3]H-nmr spectra of the products are presented.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Russell, Jeremy Colin.
Date : 1984
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THS
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1984.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 14:25
Last Modified : 06 Nov 2018 16:53
URI: http://epubs.surrey.ac.uk/id/eprint/847973

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