0000000000985603

AUTHOR

Augusto C. Tomé

0000-0003-4331-714x

showing 3 related works from this author

1,3-Dipolar cycloadditions with meso-tetraarylchlorins – site selectivity and mixed bisadducts

2017

The 1,3-dipolar cycloaddition reaction of meso-tetraarylporphyrins with nitrones gives isoxazolidine-fused chlorins. Depending on the substitution pattern on the meso-aryl groups and the nitrone, the chlorins can be obtained in high yields (up to 91%). Bacteriochlorin-type bisadducts are also obtained, although in low yield, from the reaction of meso-tetrakis(pentafluorophenyl)porphyrin with N-methyl, N-cyclohexyl or N-benzyl nitrone. The structure of a bis(N-benzyl isoxazolidine-fused) bacteriochlorin was determined by single-crystal X-ray diffraction and rationalized by DFT calculations. To further explore the nature of site selectivity in the formation of bisadducts, isomeric mixed bacte…

chemistry.chemical_classification010405 organic chemistryChemistrySite selectivityOrganic ChemistryAzomethine ylide010402 general chemistryPhotochemistry01 natural sciencesPorphyrinCycloaddition0104 chemical sciencesNitronechemistry.chemical_compoundDipoleSettore CHIM/03 - Chimica Generale E InorganicaComputational chemistryYield (chemistry)Organic Chemistry Frontiers
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Synthesis, characterization, and cellular investigations of porphyrin– and chlorin–indomethacin conjugates for photodynamic therapy of cancer

2021

Indomethacin is a potent non-steroidal anti-inflammatory drug (NSAID) with a strong selective inhibitor activity towards cyclooxygenase-2 (COX-2), an enzyme that is highly overexpressed in various tumour cells, being involved in tumourigenesis. Concomitantly, porphyrins have gained much attention as promising photosensitizers (PSs) for the non-invasive photodynamic therapy (PDT) of cancer. Herein, we report the design, and determine the singlet oxygen generation capacity and in vitro cellular toxicity of porphyrin- and chlorin-indomethacin conjugates (P2-Ind and C2-Ind). Both the conjugates were obtained in high yields and were characterized by 1H, 19F and 13C NMR as well as by high resolut…

photosensitizermedicine.medical_treatmentPhotodynamic therapyDFT calculations010402 general chemistryPhotochemistry01 natural sciencesBiochemistrychemistry.chemical_compoundnon-steroidal anti-inflammatory drugpolycyclic compoundsmedicinePhysical and Theoretical ChemistryTriplet stateCytotoxicity010405 organic chemistrySinglet oxygenOrganic Chemistrysinglet oxygen generationPorphyrin0104 chemical sciencesPhotochemotherapychemistrySettore CHIM/03 - Chimica Generale E InorganicaChlorincytotoxicityPhototoxicityporphyrinConjugateOrganic & Biomolecular Chemistry
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CCDC 1488184: Experimental Crystal Structure Determination

2017

Related Article: José Almeida, António Aguiar, Andreia Leite, André M. N. Silva, Luís Cunha-Silva, Baltazar de Castro, Maria Rangel, Giampaolo Barone, Augusto C. Tomé, Ana M. G. Silva|2017|Org.Chem.Front.|4|534|doi:10.1039/C6QO00771F

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1124-dibenzyl-271520-tetrakis(pentafluorophenyl)-1023-dioxa-112427282930-hexaazaheptacyclo[19.5.1.136.1814.11619.0913.02226]triaconta-1(27)2468(29)14161820-nonaeneExperimental 3D Coordinates
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