PHOTOCHEMISTRY OF ANTIMALARIAL DRUGS.
Abstract
The following properties of 14 quinoline methanols and quinine have been determined: ultraviolet spectra, fluorescence spectra, and quantum yields for disappearance at 313 millimicrons. Comparison of these properties with phototoxicities in mice showed no direct correlations. All the properties of compounds differing only in side chain structure were identical; their phototoxicities differ markedly. Substitution at C-3 or C-2' leads to changes in ultraviolet spectra which appear to reflect appreciable deviations from coplanarity of the quinoline and phenyl rings. Fluorescence spectra were similar for most quinoline methanols. The intensities of fluorescence did not correlate with phototoxicity. Quantum yields for disappearance of quinoline methanols ranged from zero to 0.007. These yields were a function of the degree of protonation of the compounds and the presence or absence of oxygen. On the basis of numerous values of zero for other cases, it is concluded that only the free bases of quinoline methanols in oxygen free medium can be directly responsible for phototoxicity. It is further concluded that the quinoline methanols cannot cause phototoxicity by photosensitization (energy transfer to other species). The best interpretation of the results appears to be that photoirradiation products of the free bases are phototoxic and that the degree of phototoxicity is dependent on the side chain present. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jul 01, 1968
- Accession Number
- AD0685854
Entities
People
- Mordecai B. Rubin
Organizations
- Technion – Israel Institute of Technology