Daniele Passarella
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View article: Dissecting structural and functional determinants of microtubule stabilization through guided chemical modulation
Dissecting structural and functional determinants of microtubule stabilization through guided chemical modulation Open
Paclitaxel (PTX) is a widely used chemotherapeutic, but its efficacy is limited by peripheral neuropathy, likely due to its structural impact on neuronal microtubules (MTs). To decouple MT stabilization from adverse structural changes, we …
View article: Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from <i>Cannabis sativa</i> L
Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from <i>Cannabis sativa</i> L Open
We report the first isolation of a previously unknown cannabinoid, cannabizetol (CBGD, 7), from Cannabis sativa extracts, representing the third member of the rare class of methylene-bridged dimeric cannabinoids. The availabi…
View article: Rotational Motion in Bispidines: A Conformational Study
Rotational Motion in Bispidines: A Conformational Study Open
A detailed conformational analysis of N-substituted bispidines has been performed to determine the factors governing the restricted rotational motion induced by the substituents. This investigation combines computational studies of …
View article: Asymmetric Total Synthesis of (−)‐Glycybridin B, a Pharmacophore Screened Candidate for Tubulin Binding
Asymmetric Total Synthesis of (−)‐Glycybridin B, a Pharmacophore Screened Candidate for Tubulin Binding Open
Microtubule‐targeting agents (MTAs) represent a pivotal class of therapeutic compounds designed to disrupt microtubule dynamics, leading to cell cycle arrest and apoptosis in malignant cells. Nevertheless, their off‐target effects on healt…
View article: Structure-Based Discovery of Hsp90/HDAC6 Dual Inhibitors Targeting Aggressive Prostate Cancer
Structure-Based Discovery of Hsp90/HDAC6 Dual Inhibitors Targeting Aggressive Prostate Cancer Open
HDAC6 and Heat Shock Protein 90 (Hsp90) are key regulators within the androgen response pathway, exhibiting a close interplay and mutual interaction patterns that make their combined inhibition a promising strategy for treating aggressive …
View article: Effective Tubulin Degradation by Rationally Designed Proteolysis Targeting Chimeras
Effective Tubulin Degradation by Rationally Designed Proteolysis Targeting Chimeras Open
Proteolysis targeting chimeras (PROTACs) are heterobifunctional molecules that induce the degradation of proteins of interest (POIs) via the ubiquitin-proteasome pathway by recruiting E3 ligases to form a ternary complex with the POI. In t…
View article: Synthesis and multitarget inhibitory effect of indole-based ethyl cinnamate derivatives against SARS-CoV-2 Mpro and cathepsins for broad-spectrum anti-coronavirus activity
Synthesis and multitarget inhibitory effect of indole-based ethyl cinnamate derivatives against SARS-CoV-2 Mpro and cathepsins for broad-spectrum anti-coronavirus activity Open
The experience of the SARS-CoV-2 pandemic has highlighted the urgent need to develop broad-spectrum antivirals (BSA) agents capable of targeting viral and/or host factors essential for infection as undeniable weapons against future coronav…
View article: Self-Assembled Cannabigerol-Based Nanoparticles: Design, Synthesis, and Antiproliferative Activity
Self-Assembled Cannabigerol-Based Nanoparticles: Design, Synthesis, and Antiproliferative Activity Open
Background/Objectives: Cannabigerol (CBG) is a non-psychoactive phytocannabinoid with significant therapeutic potential, showing emerging applications in drug delivery. This study aimed to develop and evaluate CBG-conjugated nanoparticles …
View article: Automated fluorine-18 radiolabeling via an alkyne–azide cycloaddition reaction on a dual peptide-functionalized liposome surface for in vivo PET imaging
Automated fluorine-18 radiolabeling via an alkyne–azide cycloaddition reaction on a dual peptide-functionalized liposome surface for in vivo PET imaging Open
Introduction Labeled nanoparticles can be monitored in the body using positron emission tomography (PET) imaging, providing real-time insights into their pharmacokinetics and biodistribution. In the present work, liposomes are labeled with…
View article: Design, synthesis and in vitro validation of bivalent binders of SARS-CoV-2 spike protein: Obeticholic, betulinic and glycyrrhetinic acids as building blocks
Design, synthesis and in vitro validation of bivalent binders of SARS-CoV-2 spike protein: Obeticholic, betulinic and glycyrrhetinic acids as building blocks Open
SARS-CoV-2 is the virus responsible for the COVID-19 pandemic, which caused over 6.7 million deaths worldwide. The Spike protein plays a crucial role in the infection process, mediating the binding of the virus to its cellular receptor, an…
View article: Revisiting the Reduction of Vinpocetine
Revisiting the Reduction of Vinpocetine Open
Hydrogenation of the semisynthetic vinca alkaloid vinpocetine produces two epimers that have previously been investigated as chiral additives. However, the absence of a full characterization generated some ambiguities in their stereochemic…
View article: Metal‐Free, Selective <i>Ortho</i>‐Deuteration of <i>N</i>‐Heterocyclic Oxides
Metal‐Free, Selective <i>Ortho</i>‐Deuteration of <i>N</i>‐Heterocyclic Oxides Open
Replacing hydrogen with deuterium raises the activation energy for C−D bond cleavage. This approach has gained attention in drug design, especially to protect the ortho ‐position of pyridines, which are susceptible to enzymatic oxidation. …
View article: Sustainable Synthesis of 1,2,3‐Triazoles using Cyrene as a Biodegradable Solvent in Click Chemistry
Sustainable Synthesis of 1,2,3‐Triazoles using Cyrene as a Biodegradable Solvent in Click Chemistry Open
The first successful synthesis of 1,2,3‐triazoles using Cyrene TM as a biodegradable and non‐toxic solvent in click chemistry has been developed. In contrast to previous methods, this sustainable approach allows product isolation by simple…
View article: An Inducible Neural Stem Progenitor Cell Model for Testing Therapeutic Interventions Against Neurodegeneration FENIB
An Inducible Neural Stem Progenitor Cell Model for Testing Therapeutic Interventions Against Neurodegeneration FENIB Open
Familial encephalopathy with neuroserpin inclusion bodies (FENIB) is a neurodegenerative pathology caused by accumulation of mutant neuroserpin (NS) polymers inside the endoplasmic reticulum (ER) of neurons, leading to cellular toxicity an…
View article: Mechanistic insights into the base-mediated deuteration of pyridyl phosphonium and ammonium salts
Mechanistic insights into the base-mediated deuteration of pyridyl phosphonium and ammonium salts Open
Base-catalyzed deuterations have been studied, computationally and experimentally, using a series of pyridyl salts with a temporary electron-withdrawing group to block the para -position while increasing the acidity in the other positions.
View article: Synthesis of α-fluorocinnamate derivatives as novel cathepsin S inhibitors with in vitro antiproliferative activity against pancreatic cancer cells
Synthesis of α-fluorocinnamate derivatives as novel cathepsin S inhibitors with in vitro antiproliferative activity against pancreatic cancer cells Open
Cathepsins, key members of the papain-like family of cysteine proteases, are crucial for proteolysis processes within human cells, including osteolysis, immunomodulation and apoptosis. Recent research has highlighted the significant role o…
View article: Metal-free, Selective Ortho-Deuteration of N-heterocyclic oxides
Metal-free, Selective Ortho-Deuteration of N-heterocyclic oxides Open
Replacing hydrogen with deuterium raises the activation energy for C‒D bond cleavage. This approach has gained attention in drug design, especially to protect the ortho-position of pyridines, which are susceptible to enzymatic oxidation. U…
View article: Mechanistic Insights into the Base-Mediated Deuteration of Pyridyl Phosphonium and Ammonium Salts
Mechanistic Insights into the Base-Mediated Deuteration of Pyridyl Phosphonium and Ammonium Salts Open
Pyridines can be deuterated at remote sites by treatment with KOtBu in DMSO-d6, although without discrimination between the meta- and para-position. Herein, base-catalyzed deuterations have been studied, computationally and experimentally,…
View article: A novel, glutathione-activated prodrug of pimasertib loaded in liposomes for targeted cancer therapy
A novel, glutathione-activated prodrug of pimasertib loaded in liposomes for targeted cancer therapy Open
A novel, glutathione-activated prodrug of pimasertib (PROPIMA) has been developed. PROPIMA showed ability to inhibit tumour cell migration and proliferation controlled over time, while also achieving a high incorporation rate into liposome…
View article: Cu-Catalyzed Asymmetric Synthesis of γ-Amino Alcohols Featuring Tertiary Carbon Stereocenters
Cu-Catalyzed Asymmetric Synthesis of γ-Amino Alcohols Featuring Tertiary Carbon Stereocenters Open
Alkyne-functionalized oxetanes are presented as versatile substrates that in combination with amine reagents can be transformed into structurally diverse, chiral γ-amino alcohols featuring a tetrasubstituted tertiary stereocenter under Cu …
View article: Nicotinic Acid Derivatives As Novel Noncompetitive α-Amylase and α-Glucosidase Inhibitors for Type 2 Diabetes Treatment
Nicotinic Acid Derivatives As Novel Noncompetitive α-Amylase and α-Glucosidase Inhibitors for Type 2 Diabetes Treatment Open
A library of novel nicotinic acid derivatives, focusing on the modification of position 6 of the pyridine ring with (thio)ether functionalities, was mostly produced through an innovative green synthetic approach (Cyrene-based) and evaluate…
View article: Total Synthesis of an Epothilone Analogue Based on the Amide‐Triazole Bioisosterism
Total Synthesis of an Epothilone Analogue Based on the Amide‐Triazole Bioisosterism Open
Epothilones are 16‐membered macrolides that act as microtubule‐targeting agents to tackle cancer. Many synthetic analogues have been investigated for their activity, yet often based on macrolide structures. A notable exception is Ixabepilo…
View article: Nirmatrelvir: From Discovery to Modern and Alternative Synthetic Approaches
Nirmatrelvir: From Discovery to Modern and Alternative Synthetic Approaches Open
The global urgency in response to the COVID-19 pandemic has catalyzed extensive research into discovering efficacious antiviral compounds against SARS-CoV-2. Among these, Nirmatrelvir (PF-07321332) has emerged as a promising candidate, exh…
View article: Front Cover: A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene (Eur. J. Org. Chem. 15/2024)
Front Cover: A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene (Eur. J. Org. Chem. 15/2024) Open
The Front Cover illustrates an efficient synthetic strategy for nucleophilic aromatic substitutions of nicotinic esters in Cyrene. This solvent, obtained from renewable cellulose waste and being non-toxic, non-mutagenic and biodegradable, …
View article: Quantitative live cell imaging of a tauopathy model enables the identification of a polypharmacological drug candidate that restores physiological microtubule interaction
Quantitative live cell imaging of a tauopathy model enables the identification of a polypharmacological drug candidate that restores physiological microtubule interaction Open
View article: A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene
A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene Open
The green solvent Cyrene TM has emerged as a valuable substitute for conventional polar aprotic organic solvents such as DMF, DMSO and NMP (renowned for their toxicity and environmental concerns). However, in the presence of bases, Cyrene …
View article: First total synthesis of caerulomycin K: a case study on selective, multiple C–H functionalizations of pyridines
First total synthesis of caerulomycin K: a case study on selective, multiple C–H functionalizations of pyridines Open
A radical change: the first 3-steps total synthesis of caerulomycin K was achieved exploiting Minisci chemistry using cheap starting materials.
View article: Targeting Ovarian Cancer with Chalcone Derivatives: Cytotoxicity and Apoptosis Induction in HGSOC Cells
Targeting Ovarian Cancer with Chalcone Derivatives: Cytotoxicity and Apoptosis Induction in HGSOC Cells Open
Ovarian cancer ranks as the eighth most prevalent form of cancer in women across the globe and stands as the third most frequent gynecological cancer, following cervical and endometrial cancers. Given its resistance to standard chemotherap…
View article: Tetraphenylethylene-Based Photoluminescent Self-Assembled Nanoparticles: Preparation and Biological Evaluation
Tetraphenylethylene-Based Photoluminescent Self-Assembled Nanoparticles: Preparation and Biological Evaluation Open
The conjugation of tetraphenylethylene (TPE) with podophyllotoxin, N-desacetylthiocolchicine, and cabazitaxel through a sebacic acid linker led to the formation of fluorescent nanoparticles. Dynamic light scattering (DLS) and photol…
View article: Recent Advances in SARS-CoV-2 Main Protease Inhibitors: From Nirmatrelvir to Future Perspectives
Recent Advances in SARS-CoV-2 Main Protease Inhibitors: From Nirmatrelvir to Future Perspectives Open
The main protease (Mpro) plays a pivotal role in the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) and is considered a highly conserved viral target. Disruption of the catalytic activity of Mpro produces a det…