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Gladiali S.,University of Sassari | Alberico E.,CNR Institute of Biomolecular Chemistry | Junge K.,Leibniz Institute for Catalysis at the University of Rostock | Beller M.,Leibniz Institute for Catalysis at the University of Rostock
Chemical Society Reviews | Year: 2011

The atropisomeric structure of 4,5-dihydro-3H-dinaphtho[2,1-c;1′, 2′-e]phosphepine is the common axially chiral scaffold of a library of monophosphine ligands nicknamed BINEPINES that have shown a quite remarkable stereoselection efficiency in a broad variety of enantioselective reactions involving the formation of new C-H or C-C or C-X bonds. In this critical review the properties and scope of this type of chiral ligands are illustrated (70 references). © 2011 The Royal Society of Chemistry.

Foti M.C.,CNR Institute of Biomolecular Chemistry
Journal of Agricultural and Food Chemistry | Year: 2015

The 2,2-diphenyl-1-picrylhydrazyl (DPPH•) radical is approaching 100 years from its discovery in 1922 by Goldschmidt and Renn. This radical is colored and remarkably stable, two properties that have made it one of the most popular radicals in a wide range of studies. First, there is the evaluation of the antioxidant abilities of phenols and other natural compounds (A-H) through a "test" that-at a closer look-is utterly inappropriate. In fact, the test-derived EC50, that is, the concentration of A-H able to scavenge 50% of the initial DPPH•, is not a kinetic parameter and hence its purported correlation with the antioxidant properties of chemicals is not justified. Kinetic measurements, such as the second-order rate constants for H-atom abstraction from A-H by DPPH•, in apolar media, are the only useful parameters to predict the antioxidant ability of A-H. Other applications of DPPH• include kinetic and mechanistic studies, kinetic solvent effects, EPR spectroscopy, polymer chemistry, and many more. In this review these applications are evaluated in detail by showing the usefulness of some and the uselessness of others. The chemistry of DPPH• is also briefly reviewed. © 2015 American Chemical Society.

Maione S.,The Second University of Naples | Costa B.,University of Milan Bicocca | Di Marzo V.,CNR Institute of Biomolecular Chemistry
Pain | Year: 2013

After 4 millennia of more or less documented history of cannabis use, the identification of cannabinoids, and of Δ9-tetrahydrocannabinol in particular, occurred only during the early 1960s, and the cloning of cannabinoid CB1 and CB2 receptors, as well as the discovery of endocannabinoids and their metabolic enzymes, in the 1990s. Despite this initial relatively slow progress of cannabinoid research, the turn of the century marked an incredible acceleration in discoveries on the "endocannabinoid signaling system," its role in physiological and pathological conditions, and pain in particular, its pharmacological targeting with selective agonists, antagonists, and inhibitors of metabolism, and its previously unsuspected complexity. The way researchers look at this system has thus rapidly evolved towards the idea of the "endocannabinoidome," that is, a complex system including also several endocannabinoid-like mediators and their often redundant metabolic enzymes and "promiscuous" molecular targets. These peculiar complications of endocannabinoid signaling have not discouraged efforts aiming at its pharmacological manipulation, which, nevertheless, now seems to require the development of multitarget drugs, or the re-visitation of naturally occurring compounds with more than one mechanism of action. In fact, these molecules, as compared to "magic bullets," seem to offer the advantage of modulating the "endocannabinoidome" in a safer and more therapeutically efficacious way. This approach has provided so far promising preclinical results potentially useful for the future efficacious and safe treatment of chronic pain and inflammation. © 2012 International Association for the Study of Pain. Published by Elsevier B.V. All rights reserved.

Casiraghi G.,University of Parma | Battistini L.,University of Parma | Curti C.,University of Parma | Rassu G.,CNR Institute of Biomolecular Chemistry | Zanardi F.,University of Parma
Chemical Reviews | Year: 2011

Methodology-oriented and target-oriented researches focused on the various aspects of the vinylogous aldol addition reaction and studies devoted to the related Mannich (VMnR) and Michael (VMcR) processes are summarized. Gademann et al. constructed stereoisomeric seven carbon long galantinic acid substructures during a biomimetic total synthesis of anachelin H, an iron chelator isolated from the cyanobacterium Anabaena cylindrica. Suenaga and co-workers have investigated the stereostructure of Palau'amide by total synthesis, utilizing a VMAR addition as the key step of the entire construction. Kobayashi and co-workers introduced a series of acyclic vinyl ketene silyl N,O-acetals as chiral d4 donor substrates in VMAR processes. Boeckman Jr. et al employed Corey chiral oxazaborolidine to fuel the asymmetric VMAR between silyloxy furan and chiral nonracemic aldehyde.

Di Marzo V.,CNR Institute of Biomolecular Chemistry | De Petrocellis L.,Olivetti
Philosophical Transactions of the Royal Society B: Biological Sciences | Year: 2012

The endocannabinoid system was revealed following the understanding of the mechanism of action of marijuana's major psychotropic principle, Δ9-tetrahydrocannabinol, and includes two G-proteincoupled receptors (GPCRs; the cannabinoid CB1 and CB2 receptors), their endogenous ligands (the endocannabinoids, the best studied of which are anandamide and 2-arachidonoylglycerol (2-AG)), and the proteins that regulate the levels and activity of these receptors and ligands. However, other minor lipid metabolites different from, but chemically similar to, anandamide and 2-AG have also been suggested to act as endocannabinoids. Thus, unlike most other GPCRs, cannabinoid receptors appear to have more than one endogenous agonist, and it has been often wondered what could be the physiological meaning of this peculiarity. In 1999, it was proposed that anandamide might also activate other targets, and in particular the transient receptor potential of vanilloid type-1 (TRPV1) channels. Over the last decade, this interaction has been shown to occur both in peripheral tissues and brain, during both physiological and pathological conditions. TRPV1 channels can be activated also by another less abundant endocannabinoid, N-arachidonoyldopamine, but not by 2-AG, and have been proposed by some authors to act as ionotropic endocannabinoid receptors. This article will discuss the latest discoveries on this subject, and discuss, among others, how anandamide and 2-AG differential actions at TRPV1 and cannabinoid receptors contribute to making this signalling system a versatile tool available to organisms to fine-tune homeostasis. © 2012 The Royal Society.

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