Preoperative Prediction of Whether Intraoperative Fluorescence of Protoporphyrin IX Can Be Achieved by 5-Aminolevulinic Acid Administration
Satoshi UtsukiHidehiro OkaChihiro KijimaMadoka InukaiKiyotaka FujiiMasahiro IshizukaKiwamu TakahashiKatsushi Inoue
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Abstract:
Protoporphyrin IX (PPIX) fluorescence-guided brain tumor resection, using 5-aminolevulinic acid (5-ALA), is among the most valuable tools for determining tumor removal area. However, PPIX fluorescence is not necessarily achieved during an operation visually even when 5-ALA is used, and we do not know until tumor exposure to the excitation light of the ultraviolet region whether PPIX fluorescence has been achieved. When a particular biopsy and frozen section diagnosis is made, the reason for lack of PPIX fluorescence in the tissue cannot be judged. We do not know whether the tumor fails to fluoresce or no fluorescence is seen because it is not the main body of the tumor. We investigated whether the presence or absence of tumor fluorescence could be predicted by examining urinary porphyrin before surgery, at the time of intraoperative fluorescence diagnosis using 5-ALA. The urine of brain tumor patients 2 hours after 5-ALA administration was irradiated with a 405 ± 1 nm laser light. The patients were divided into a fluorescent urine group and negative fluorescent urine group. Red fluorescence was observed in response to the 405 ± 1 nm laser beam for all tumors in the fluorescent urine group. Clear red fluorescence was not observed even with 405 ± 1 nm laser beam irradiation in any tumors in the negative fluorescent urine group. Preoperative prediction of the intraoperative fluorescence of PPIX can be achieved by observation of urine 2 hours after 5-ALA administration with exposure to a 405 ± 1 nm laser light.Keywords:
Protoporphyrin IX
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The LB films forming properties of two hydroxyl-substituted porphyrins with double hexadecyl chains have been characterized. UV-Vis spectra show that the two porphyrins possess various aggregation behaviors in LB films. The porphyrin with symmetrically attached chains tend to form J-aggregate and the other asymmetric porphyrin can form hydrogen-bonded aggregate in LB films. The orientation of porphyrin rings was examined by polarized UV-Vis spectra. The results indicate that the situation of side-chain attached on porphyrin ring has no influence on porphyrin ring orientation, but has great influence on mean molecular areas or the distanses between porphyrin rings, and so as to affect the aggregation behaviors of porphyrin in LB films.
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A strategy for the synthesis of asymmetrically substituted tetraazaanthracene linked bis-porphyrins in which the two porphyrin rings contain differences in their peripheral substituents has been developed. The method is illustrated by the preparation of bis-porphyrins with a single meso-halophenyl and seven meso-3,5-di-tert-butylphenyl substituents. The bis-porphyrins were prepared by condensation of a porphyrin-α-dione with benzene-1,2,4,5-tetraamine to form a porphyrin diaminoquinoxaline intermediate which was subsequently condensed with a second different porphyrin-α-dione. The key issue in the synthesis was the separation of the desired asymmetrically substituted bis-porphyrin from the symmetric bis-porphyrin by-products of similar polarities. Enhanced separation of the bis-porphyrin products was achieved by chelation of a metal into one of the porphyrin rings, the metal being introduced at the porphyrin-α-dione stage. Copper was successfully used when chelated into the less polar porphyrin-α-dione but the use of zinc in the more polar porphyrin-α-dione to enhance bis-porphyrin separation was unsuccessful as the pyridinium hydrochloride produced in the reaction was found to demetallate the porphyrins.
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Protoporphyrin IX
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