Alessandro Palmioli

Alessandro Palmioli
Università degli Studi di Milano-Bicocca | UNIMIB · Department of Biotechnology and Biosciences

PhD in Chemistry

About

46
Publications
6,412
Reads
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695
Citations
Introduction
Currently, my research activities mainly focused on: 1. Design and synthesis of bioactive compounds. 2. Design and synthesis of polyvalent and nanostructured glycoconjugates. 3. Identification and characterization of bioactive molecules in natural and edible sources. My technical expertise covers up-to-date synthetic methods, purification and analysis of organic molecules, natural compounds and peptides, NMR spectroscopy and mass spectrometry. I am strongly experienced in evaluating structure-activity relationship, structure optimization of putative bioactive compounds (rational drug design) and identification of bioactive molecules in natural sources. Skilled in carbohydrate and peptide chemistry, chemoselective bioconjugations, chromatographic techni
Additional affiliations
July 2016 - present
Università degli Studi di Milano-Bicocca
Position
  • PostDoc Position
July 2012 - December 2013
University of Milan
Position
  • PostDoc Position
April 2010 - March 2011
DiaSorin
Position
  • Researcher
Education
November 2006 - December 2009
Università degli Studi di Milano-Bicocca
Field of study
  • Bioorganic Chemistry
October 1999 - February 2005
Università degli Studi di Milano-Bicocca
Field of study
  • Industrial Biotechnology

Publications

Publications (46)
Article
Full-text available
The anti-Alzheimer disease (AD) activity reported for an aqueous cinnamon bark extract prompted us to investigate and compare the anti-amyloidogenic properties of cinnamon extracts obtained from both bark and bud, the latter being a very little explored matrix. We prepared the extracts with different procedures (alcoholic, hydroalcoholic, or aqueou...
Article
Full-text available
The anti-inflammatory activity of coffee extracts is widely recognized and supported by experimental evidence, in both in vitro and in vivo settings, mainly murine models. Here, we investigated the immunomodulatory properties of coffee extracts from green (GCE) and medium-roasted (RCE) Coffea canephora beans in human macrophages. The biological eff...
Chapter
Many biologically relevant molecular recognition processes are highly dynamic and rely on the equilibrium between ligands’ association and dissociation from their receptor(s), because of the reversible nature of the majority of them. Over the last few decades, several NMR experiments allowing the characterization of these interactions have been dev...
Article
Full-text available
Proteasome inhibitors (PIs) represent the gold standard in the treatment of multiple myeloma. Among PIs, Bortezomib (BTZ) is frequently used as first line therapy, but peripheral neuropathy (PN), occurring approximately in 50% of patients, impairs their life, representing a dose-limiting toxicity. Carfilzomib (CFZ), a second-generation PI, induces...
Article
Peucedanum ostruthium (L.) W.D.J.Koch (Apiaceae) is an alpine medicinal plant traditionally used as a panacea to treat various ailments. For the first time, its phytotoxic and nematotoxic properties were investigated. The inhibitory activity toward germination and seedling growth of the weeds Echinochloa oryzoides (Ard.) Fritsch and Lolium multiflo...
Article
We describe the development of an on-cell NMR method for the rapid screening of FimH ligands and the structural identification of ligand binding epitopes. FimH is a mannose-binding bacterial adhesin expressed at the apical end of type 1 pili of uropathogenic bacterial strains and responsible for their D-mannose sensitive adhesion to host mammalian...
Article
We report the rational design, synthesis, and in vitro preliminary evaluation of a new small library of non-peptide ligands of Gastrin Releasing Peptide Receptor (GRP-R), able to antagonize its natural ligand bombesin (BN) in the nanomolar range of concentration. GRP-R is a transmembrane G-protein coupled receptor promoting the stimulation of canc...
Article
Full-text available
Ras oncoproteins play a crucial role in the onset, maintenance, and progression of the most common and deadly human cancers. Despite extensive research efforts, only a few mutant-specific Ras inhibitors have been reported. We show that cmp4-previously identified as a water-soluble Ras inhibitor-targets multiple steps in the activation and downstrea...
Chapter
Substitution with a carbon or a sulfur atom of the oxygen that in saccharides links one sugar unit to another sugar or to an aglycon generates compounds defined as C-glycosides and S-glycosides, respectively. The interest in these classes of compounds lies in the metabolic stability of the glycosidic linkage, as useful characteristic for potential...
Article
Full-text available
Palmitoylethanolamide (PEA) belongs to the class of N-acylethanolamine and is an endogenous lipid potentially useful in a wide range of therapeutic areas; products containing PEA are licensed for use in humans as a nutraceutical, a food supplement, or food for medical purposes for its analgesic and anti-inflammatory properties demonstrating efficac...
Article
The metabolic profile of Lavado cocoa was characterized for the first time by NMR spectroscopy, then compared with the profiles of fermented and processed varieties, Natural and commercial cocoa. The significant difference in the contents of theobromine and flavanols prompted us to examine the cocoa varieties to seek correlations between these meta...
Article
Full-text available
Rice cultivation, particularly prone to weed issues, requires practices able to effectively control them, however reducing the use of herbicides, responsible for damage to human health and ecosystem sustainability. Alternative strategies for weed management can be based on plant-plant interaction phenomena. In this context, a group of organic farme...
Article
The authentication and traceability of craft beers is an important issue for both beer consumers and producers. Reliable analytical methods able to identify and discriminate products are needed to protect the craft brew market against fraud and counterfeit. Here, 1H-NMR analysis of 31 beer samples, differing for beer style and brewing method (craft...
Article
We report the NMR characterization of the molecular interaction between Gastrin Releasing Peptide Receptor (GRP-R) and its natural ligand bombesin (BN). GRP-R is a transmembrane G-protein coupled receptor promoting the stimulation of cancer cell proliferation; in addition, being overexpressed on the surface of different human cancer cell lines, it...
Article
Full-text available
Mint [Mentha longifolia (L.) Hudson] is an aromatic plant that belongs to Lamiaceae family. It is traditionally used as herbal tea in Europe, Australia and North Africa and shows numerous pharmacological effects, such as spasmolytic, antioxidant, antimicrobial and anti-hemolytic. Recently, its antiproliferative role has been suggested in a small nu...
Article
Together with the development of new therapeutic agents, innovation in the delivery system of anti-tumor drugs is required to increase tumor-specificity and avoid unexpected toxicity. To achieve higher efficiency, we combined a live cell-mediated drug delivery system with nanotechnology, with the aim to prove that blood monocytes can be a cargo to...
Article
Biofilm formation by bacterial pathogens is a hallmark of chronic infections and is associated to increased antibiotic tolerance that makes pathogens difficult to eradicate with conventional antibiotic therapies. Infections caused by Pseudomonas aeruginosa are of great concern, especially for immunocompromised and cystic fibrosis patients. P. aerug...
Article
The growing interest in medicinal plants for the identification of new bioactive compounds and the formulation of new nutraceuticals and drugs prompted us to develop a powerful experimental approach allowing the detailed metabolic profiling of complex plant extracts, the identification of ligands of macromolecular targets of biomedical relevance an...
Article
Carbohydrates are one of the most powerful and versatile classes of biomolecules that nature uses to regulate organisms biochemistry, able to regulate plenty of signaling events within cells, triggering a plethora of physiological and pathological cellular behaviors. In this framework, glycan carrier systems or carbohydrate-decorated materials cons...
Article
The design, synthesis and characterization of novel glycoconjugate luminescent probes based on dinuclear rhenium(I) complex are reported. A multivalent platform bearing different carbohydrate moieties (Glc, Gal and Man) was used to target carbohydrate-binding proteins (lectins), exploiting the unique photophysical charateristics of Re(I) luminophor...
Article
A set of poly(lactic-co-glycolic acid) polymers functionalized with different monosaccharides as well as glycodendrimers and surface-decorated nanoparticles (NPs) were synthesized and characterized. The functionalization of the polymer was carried out through amide bond formation with amino-modified sugar monomers and through a biocompatible chemos...
Article
Flavonoids are phytochemicals present in almost all terrestrial plants and, as a consequence, in plant-based foods, and thus consumed by humans through the diet. Recent evidences suggest that several flavonoids have positive effects against dementia and Alzheimer's disease, reversing age-related declines in neurocognitive performances. In this revi...
Article
To identify food and beverages that provide the regular intake of natural compounds capable of interfering with toxic amyloidogenic aggregates, we developed an experimental protocol that combines NMR spectroscopy and atomic force microscopy, in vitro biochemical and cell assays to detect anti-Aβ molecules in natural edible matrices. We applied thi...
Article
Recent epidemiological studies demonstrate that consumption of healthy foods, especially rich in polyphenols content, might reduce the incidence of cancer and degenerative diseases. In particular, chlorogenic acids (CGAs) occur ubiquitously in food, representing the most abundant polyphenols in the human diet. A number of CGA beneficial biological...
Article
Nutritional factors play a pivotal role for healthy aging and longevity. This is related to the antioxidant properties of the molecules present in some foods. Due to the high content of polyphenols, Green Coffee Extract (GCE) is a powerful antioxidant. Nevertheless, little is known about its effect on aging. We demonstrated the benefic effects of G...
Article
The design, synthesis and photophysical characterization of four new luminescent glycosylated luminophores based on dinuclear rhenium complexes, namely Glyco-Re, are described. The derivatives have the general formula [Re2(μ-Cl)2(CO)6(μ-pydz-R)] (R-pydz = functionalized 1,2-pyridazine), where a sugar residue (R) is covalently bound to the pyridazin...
Article
Full-text available
The initial steps of viral infections are mediated by interactions between viral proteins and cellular receptors. Blocking the latter with high-affinity ligands may inhibit infection. DC-SIGN, a C-type lectin receptor expressed by immature dendritic cells and macrophages, mediates human immunodeficiency virus (HIV) infection by recognizing mannose...
Article
Mannose-binding lectin is present in the contusion area of traumatic brain-injured patients and in that of traumatic brain-injured mice, where mannose-binding lectin-C exceeds mannose-binding lectin-A. The reduced susceptibility to traumatic brain injury of mannose-binding lectin double knock-out mice (mannose-binding lectin−/−) when compared to wi...
Article
Mannose-binding lectin (MBL) is a circulating protein that acts as a soluble pattern recognition molecule of the innate immunity. It binds to carbohydrate patterns on the surface of pathogens or of altered self-cells, with activation of the lectin pathway of the complement system. Recent evidence indicates that MBL contributes to the pathophysiolog...
Article
Full-text available
Glycodendrimers based on aromatic cores have an amphiphilic character and have been reported to generate supramolecuar assemblies in water. A new group of glycodendrimers with an aromatic rod-like core were recently described as potent antagonists of DC-SIGN-mediated viral infections. A full characterization of the aggregation properties of these m...
Article
Antagonists of MBL have shown a protective role against brain reperfusion damage after acute ischemic stroke. Here we describe the design and streamlined synthesis of glycomimetic MBL antagonists based on a new tetravalent dendron scaffold. The dendron was developed by optimization of a known polyester structure previously demonstrated very efficie...
Article
Full-text available
The abortion-prone mating combination CBA/J × DBA/2 has been recognized as a model of preeclampsia, and complement activation has been implicated in the high rate of pregnancy loss observed in CBA/J mice. We have analyzed the implantation sites collected from DBA/2-mated CBA/J mice for the deposition of the complement recognition molecules using CB...
Article
The interaction of carbohydrates with a variety of biological targets, including antibodies, proteins, viruses and cells are of utmost importance in many aspects of biology. Glycan microarrays are increasingly used to determine the binding specificity of glycan-binding proteins. In this study, a novel slide is reported for the fabrication of glycan...
Article
Full-text available
Providing an effective mucosal barrier to HIV infection will be essential to stop the HIV epidemic, since the large majority of new infections occur at the genital level. One of the molecular targets present in mucosae and exploited by the virus to invade the host is the dendritic cell receptor DC-SIGN, a tetrameric C-type lectin that recognizes HI...
Article
Full-text available
In the last decades, food science has greatly developed, turning from the consideration of food as mere source of energy to a growing awareness on its importance for health and particularly in reducing the risk of diseases. Such vision led to an increasing attention towards the origin and quality of raw materials as well as their derived food produ...
Article
We report the synthesis and the characterization of N-(4-aminobutyl)-N-ethyl-isoluminol (ABEI) macrocyclic lactone, an activated ester with an unusual macrocyclic structure, and its use for efficient ABEI conjugation to proteins. Compared to the equivalent reagent normally used for chemiluminescence protein labeling, the ABEI macrocyclic lactone di...
Patent
Full-text available
The invention relates to a new molecule/reagent family, N-(4-Aminobutyl)-N- ethylisoluminol anhydroglutarate (ABEI anhydroglutarate), for the covalent attachment of the chemiluminescent label N-(4-Aminobutyl)-N-ethylisoluminol (ABEI) to nucleophilic group containing molecules, as peptides and proteins, including antibodies, for the generation of la...
Article
Full-text available
Since mutations of Ras genes have a great incidence in human tumours, Ras oncoproteins are a major clinical target for the development of anticancer agents. We have developed synthetic molecules able to inhibit Ras activation. Here we present new, water-soluble Ras inhibitors composed by an aromatic pharmacofore moiety covalently linked to differen...
Article
Full-text available
This paper reports the synthesis of a panel of small molecules with arylamides and arylsulfonamides groups and their biological activity in inhibiting nucleotide exchange on human Ras. The design of these molecules was guided by experimental and molecular modelling data previously collected on similar compounds. Aim of this work is the validation o...
Article
Full-text available
This paper reports the synthesis of a panel of small molecules with arylamides and arylsulfonamides groups and their biological activity in inhibiting nucleotide exchange on human Ras. The design of these molecules was guided by experimental and molecular modelling data previously collected on similar compounds. Aim of this work is the validation o...
Article
Mutation of RAS genes is a critical event in the pathogenesis of different human tumors and in some developmental disorders. Here we present an arabinose-derived bicyclic compound displaying selective cytotoxicity in human colorectal cancer cells expressing K-Ras(G13D), that shows high intrinsic nucleotide exchange rate. We characterize binding of...
Article
By combining in the same molecule Ras-interacting aromatic moieties and a sugar, we prepared a water-soluble Ras ligand that binds Ras and inhibits guanine nucleotide exchange. With this compound it was possible to determine experimentally by a (15)N-edited HSQC NMR experiment the ligand-Ras binding interface.
Article
Too complex to change. New glucose-derived phenylhydroxylamines inhibit nucleotide exchange on human Ras. NMR and SPR experiments indicated that the Ras-GEF interaction is inhibited when the Ras-ligand complex is formed. (Chemical Equation Presented).

Questions

Question (1)
Question
I want to collect the emission spectra of a glyco-fluorescent probe during titration with a Lectin like ConA or PNA, that agglutinate as result of binding. The resulting agglutinate solution has a lot of background and scattering signal that hinder the emission spectra.
Any experience about that? instrumental trick?

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Projects

Projects (5)
Project
We exploit NMR-based molecular recognition studies and organic synthesis for the rational development of new antibacterial agents