Fullerene derivatives: an attractive tool for biological applications

In this review, we address a highly interdisciplinary field: the use of nanomaterials as carriers for singlet oxygen photosensitizers and their potential applications in photodynamic therapy. In particular, recent advances in the use of nanoparticles including inorganic oxide-, metallic-, and polymer-based nanocomposites as photosensitizer carriers are highlighted. We review advantages and shortcomings of these diverse approaches as far as their application for photodynamic therapy is concerned. Fullerenes and their derivatives are also included, focusing on recent studies on their structure, properties, and ability to generate singlet oxygen.

Nanomaterials and singlet oxygen photosensitizers: potential applications in photodynamic therapy

Recent developments in the chemistry of dihydropyridines

The biheteroaryl structural motif is prevalent in polymers, advanced materials, liquid crystals, ligands, molecules of medicinal interest, and natural products. Many types of synthetic transformations have been known for the construction of heteroaryl–heteroaryl linkages. Coupling reactions provide one of the most efficient ways to achieve these biheterocyclic structures. In this review, four types of coupling reactions are discussed: 1) transition-metal-catalyzed coupling reactions of heteroaryl halides or surrogates with heteroarylmetals; 2) direct inter- and intramolecular heteroarylations of CH bonds of heteroarenes with heteroaryl halides or pseudohalides; 3) oxidative CH/CH homo- and cross-couplings of two unpreactivated heteroarenes; and 4) transition-metal-catalyzed decarboxylative cross-coupling reactions between haloheteroarenes or heteroarenes and heteroarenecarboxylic acids. The general purpose of this review is to give an exhaustive and clear picture in heteroaryl–heteroaryl bond formation as well as its application in the synthesis of natural products, pharmaceuticals, catalyst ligands, and materials.

Recent Progress in Coupling of Two Heteroarenes

Preface 1 - Twenty Years of Promises: Fullerene in Medicinal Chemistry Tatiana Da Ros 2 - Biomedical Applications of Functionalised Carbon Nanotubes Alberto Bianco, Raquel Sainz, Shouping Li, Helene Dumortier, Lara Lacerda, Kostas Kostarelos, Silvia Giordani, and Maurizio Prato 3 - Antioxidant Properties of Water-Soluble Fullerene Derivatives Florian Beuerle, Russell Lebovitz, and Andreas Hirsch 4 - Fullerenes as Photosensitizers in Photodynamic Therapy Pawel Mroz, George P. Tegos, Hariprasad Gali, Timothy Wharton, Tadeusz Sarna, and Michael R. Hamblin 5 - Photodynamic Inactivation of Enveloped Viruses by Fullerene: Study of Efficacy and Safety Vladimir V. Zarubaev, Oleg Kiselev, Inna Belousova, Vladimir Rylkov, Alexander Slita, Alexey Sirotkin, Pavel Anfimov, Tatyana Muraviova, and Andrey Starodubtsev 6 - Effects of Photoexcited Fullerene C60-Composites in Normal and Transformed Cells S.V. Prylutska, I.I. Grynyuk, O.P. Matyshevska, A.A. Golub, A.P. Burlaka, Yu.I. Prylutskyy, U. Ritter, and P. Scharff 7 - Biological Effects in Cell Cultures of Fullerene C60: Dependence on Aggregation State Levon B. Piotrovsky, Mikhail Yu. Eropkin, Elena M. Eropkina, Marina A. Dumpis, and Oleg I. Kiselev 8 - Gadolinium Endohedral Metallofullerene-Based MRI Contrast Agents Robert D. Bolskar 9 - Biomolecules Functionalized Carbon Nanotubes and Their Applications Daxiang Cui 10 - Applications of Carbon-Based Nanomaterials for Drug Delivery in Oncology Nicole H. Levi-Polyachenko, David L. Carroll, and John H. Stewart,IV 11 - Visualization of Carbon Nanoparticles Within Cells and Implications for Toxicity Alexandra Porter 12 - Pharmacological Applications of Biocompatible Carbon Nanotubes and Their Emerging Toxicology Issues Tae-Joon Park, Jeffrey G. Martin, and Robert J. Linhardt 13 - Solubility of Fullerenes in Fatty Acids Esters: A New Way to Deliver In Vivo Fullerenes. Theoretical Calculations and Experimental Results Franco Cataldo 14 - New Approach to QSPR Modeling of Fullerene C60 Solubility in Organic Solvents: An Application of SMILES-Based Optimal Descriptors A.A. Toropov, B.F. Rasulev, D. Leszczynska, and J. Leszczynski 15 - Functionalized Nanomaterials to Sense Toxins/Pollutant Gases Using Perturbed Microwave Resonant Cavities Aman Anand, J.A. Roberts, and J.N. Dahiya 16 - Cellular Nanotubes: Membrane Channels for Intercellular Communication Raquel Negrao Carvalho and Hans-Hermann Gerdes

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Medicinal Chemistry and Pharmacological Potential of Fullerenes and Carbon Nanotubes

Synthesis of water soluble fulleropyrrolidines bearing biologically active arylpiperazines

Synthesis of new C60 derivatives containing biologically active 4-aryl-1,4-dihydropyridines

A comparative study of the palladium-catalyzed arylation and heteroarylation of 5-bromoazolopyrimidines shows that aryl and electron-rich heteroaryl boronic acids gave higher yields than those obtained using the corresponding aryl and heteroaryl tributyl stannanes. In contrast, the reaction with electron-poor heteroaryl tributyl stannanes gave better results than the corresponding boronic acids.

Palladium-Catalyzed Arylation and Heteroarylation of Azolopyrimidines

A new synthetic approach to N-substituted 1,4-dihydropyridines

New substituted 2-amino-3-cyano-4H-pyrans have been studied by electron ionization (EI), chemical ionization (CI) and electrospray ionization (ESI) mass spectrometry. The retro-Diels-Alder reaction (RDA) is the main fragmentation pattern observed in the EI spectra forming an unsaturated ketone as the diene fragment. In contrast, a different RDA reaction takes place yielding an unsaturated amide as diene fragment together with the unsaturated ketone in the CI spectra. The MS/MS spectra obtained using an ESI source reveal that the favoured fragmentation by collision induced dissociation (CID) is the elimination of the substituent at the C4 position with formation of a stable pyrilium cation. Copyright © 2000 John Wiley & Sons, Ltd.

Javier Fernandez‐Gadea

Papers

Synthesis of water soluble fulleropyrrolidines bearing biologically active arylpiperazines

Synthesis of new C60 derivatives containing biologically active 4-aryl-1,4-dihydropyridines

Palladium-Catalyzed Arylation and Heteroarylation of Azolopyrimidines

A new synthetic approach to N-substituted 1,4-dihydropyridines

Mass spectra of new substituted 2-amino-4H-pyrans: a retro-Diels-Alder reaction pattern.