Aluminium phthalocyanines sulfonated to a different degree ( AlPcS n ) and consisting of various isomeric species were studied by spectroscopic techniques to determine their tendencies to form dimers and aggregates. These characteristics were compared with the cell-penetrating properties of the species, using the Ehrlich ascites mouse tumor cell line, to arrive at structure-activity relationships. AlPcS n preparations consisting of the least number of isomeric species exhibited the highest tendency to form dimers and aggregates, whereas the more complex preparations, consisting of many isomeric products, showed more consistent monomeric features in aqueous environments. Uptake in cells was shown to correlate well with the overall hydrophobicity of the preparation and inversely with its degree of aggregation in the extracellular environment. Among the purified, single isomeric AlPcS n the amphiphilic disulfonated AlPcS 2a , enriched in positional isomers featuring sulfonate groups on adjacent phthalic subunits, showed the best membrane-penetrating properties. Even higher cell uptake was observed for the AlPcS 2mix reflecting a combination of optimal lipophilicity and a low degree of aggregation. Similarly, in the case of AlPcS 4 , the pure isomeric compound showed less cell uptake than the mixed isomeric preparation of similar hydrophobicity, reflecting the higher degree of aggregation invoked by its symmetrical structure. Our data indicate that mixed sulfonated phthalocyanine preparations may exert higher photodynamic efficacy in biological applications as compared to the pure isomeric constituents.

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Journal of Labelled Compounds and RadiopharmaceuticalsVolume 26, Issue 1-12 p. 342-343 Symposium Abstract Synthesis of NCA 7α-(11-[18F]fluoroundecyl)-estradiol: Evaluation of a vector for estrogen receptor based agents J.N. Dasilva, J.N. Dasilva MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada J1H 5N4Search for more papers by this authorC. Crouzel, C. Crouzel CEA Service Hospitalier Frédéric Joliot, 91406 Orsay, FranceSearch for more papers by this authorJ.E. van Lier, J.E. van Lier MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada J1H 5N4Search for more papers by this author J.N. Dasilva, J.N. Dasilva MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada J1H 5N4Search for more papers by this authorC. Crouzel, C. Crouzel CEA Service Hospitalier Frédéric Joliot, 91406 Orsay, FranceSearch for more papers by this authorJ.E. van Lier, J.E. van Lier MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada J1H 5N4Search for more papers by this author First published: January 1989 https://doi.org/10.1002/jlcr.25802601148Citations: 4AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume26, Issue1-12January 1989Pages 342-343 RelatedInformation

The epimeric 20-hydroperoxy derivatives of cholesterol react rapidly and quantitatively with stoichiometric amounts of highly purified adrenocortical mitochondrial cytochrome P-450 scc . In this system, the sterols serve both as substrate and as source of the activated oxygen for the stereospecific hydroxylation of the carbon atom adjacent to the hydroperoxy group. We have identified the 22R-hydroxy- and 20α, 22R-dihydroxycholesterols as enzyme-bound constituents of bovine cytochrome P-450 scc .

Ionized14CO gas provides a rapid method for producing14C-labelled biomolecules. The apparatus consists of a high vacuum system in which a small amount of14CO is ionized by electron impact. The resulting species drift towards a target where they interact with the molecule of interest to produce14C-labelled compounds. Since the reaction time is only 2 minutes, the method is particularly promising for producing tracer biomolecules with short-lived11C at high specific activities. We have studied the applicability of the method to various classes of compounds of biological importance, including sterids, alkaloids, prostaglandins, nucleosides, amino acids and proteins. All compounds treated gave rise to14C addition and degradation products. Furthermore, for some compounds, chromatographic analysis in multiple systems followed by derivatization and crystallization to constant specific activity, indicated that carbon exchange may occur to produce the labelled, but otherwise unaltered substrate in yields of the order of 10–100 mCi/mol. More conclusive proof of radiochemical identity must await production of larger quantities of material and rigorous purification including at least two different chromatographic techniques.

Incubation of 20α-hydroperoxycholesterol (I) and its 20β-isomer, 20β-hydroperoxy-20-isocholesterol (II) with adrenocortical mitochondrial preparations in the absence of molecular oxygen, in normal and 18O-enriched water, gave 20α,22R-dihydroxycholesterol (III) from I and 20β,21-dihydroxy-20-iso-cholesterol (IV) from II. Mass spectral analysis of the persilylated glycol products III and IV showed no uptake of 18O, indicating that the oxygen atoms of the C20-, C22- and C21-hydroxyl groups originated from the 20-hydroperoxy groups of the substrates. This work supports the suggestion that a ferrylatomic oxygen complex is the intermediate in the enzymic oxidative reactions of cholesterol side-chain cleavage.