{"id":17,"date":"2018-11-19T19:50:38","date_gmt":"2018-11-19T19:50:38","guid":{"rendered":"https:\/\/sites.unimi.it\/passalab\/home\/"},"modified":"2026-10-05T16:27:44","modified_gmt":"2026-10-05T14:27:44","slug":"home","status":"publish","type":"page","link":"https:\/\/sites.unimi.it\/passalab\/","title":{"rendered":""},"content":{"rendered":"\n

PassaLab<\/strong><\/h2>\n\n\n\n
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Professor Daniele Passarella\u2019s Research Group<\/strong>
Department of Chemistry<\/strong><\/a>
University of Milan<\/strong><\/a><\/p>\n<\/div><\/div>\n<\/div>\n<\/div>\n\n\n\n

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Self-Assembled
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Diversity-Oriented
Synthesis<\/h3><\/div>
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Synthesis
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Natural Products
as Leads<\/h3><\/div>
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Check out our latest publications! <\/em><\/strong><\/p>\n\n\n\n

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Dissecting Structural and Functional Determinants of Microtubules Stabilization through Guided Chemical Modulation<\/strong><\/h2>\n\n\n\n
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J. Med. Chem.\u00a02026<\/strong><\/em><\/p>\n\n\n\n

Paclitaxel (PTX) is a widely used microtubule (MT) stabilizer whose clinical utility is limited by peripheral neuropathy, likely due to drug-induced structural perturbations of neuronal MTs. Here, we aimed to discern how taxane derivatives modify MT lattice architecture and how structural states regulate motor proteins and MAP dynamics. To decouple MT stabilization from adverse structural changes, we designed, synthesized, and characterized several PTX analogues. Our compound 1b<\/strong> retains PTX-like stabilizing activity in vitro<\/em> and in cells while preserving a native-like MT lattice. This structural separation allowed direct interrogation of MT structure\u2013function relationship in cells. PTX-induced lattice expansion disrupted dynein-mediated retrograde transport, altered kinesin-1 motility and suppressed dynamic Tau exchange. In contrast, 1b<\/strong> preserved more physiological Tau dynamics. These findings reveal that MT stabilization and lattice modulation are separable properties and establish drug-imposed MT states as regulators of intracellular transport and MAP behavior.<\/p>\n\n\n\n

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PROTAC-mediated degradation of peroxisomal d-aspartate oxidase: A novel strategy to modulate d-aspartate homeostasis for schizophrenia treatment<\/strong><\/h2>\n\n\n\n
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Eur. J. Med. Chem., 2026<\/strong><\/em><\/p>\n\n\n\n

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Guided by STD-NMR, we designed a series of heterobifunctional degraders integrating a hDASPO-binding ligand (olanzapine) with established E3 ligase recruiters (lenalidomide or VH032\u2013Me) and aliphatic linkers of varying lengths. The resulting bifunctional compounds were synthesized and evaluated in biochemical assays for their ability to bind hDASPO. Most compounds retained micromolar
inhibitory activity, indicating that derivatization at olanzapine position 10 preserves target engagement, with CRBN-recruiting analogues generally outperforming their VHL-based counterparts. Selected compounds were further investigated in cellular models, where PROTAC 17 demonstrated robust target engagement, positive cooperativity in ternary complex formation and dose-dependent degradation of hDASPO. Find out more here<\/a>.<\/p>\n\n\n\n

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N<\/em>-Amidinyl-Benzodiazaborines as Novel Boron-Based Scaffolds: Synthesis and Application in Retromer Stabilization<\/h2>\n\n\n\n

Adv. Synth. Catal., 2026<\/em><\/strong><\/p>\n\n\n\n

Diazaborines, a class of boron-containing compounds known for their antibacterial activity, are synthesized from 2-formylphenylboronic acid and hydrazines. Yet, the use of aminoguanidine has never been explored; thus, no examples of N-amidinyl-benzodiazaborines have been reported to date. Herein, we computationally and experimentally investigated the synthesis and characterization of novel N-amidinyl-benzodiazaborines, showing how these heteroaryl guanyl hydrazones are able to stabilize the retromer, a protein complex whose malfunction impairs the disposal of neurotoxic protein aggregates in neurodegenerative diseases such as Parkinson\u2019s disease (PD) and amyotrophic lateral sclerosis (ALS).<\/p>\n\n\n\n

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Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti- inflammatory Activity and Extraction from Cannabis sativa L<\/em><\/strong><\/h2>\n\n\n\n
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J. Nat. Prod., 2025<\/em><\/strong><\/p>\n\n\n\n

We report the first isolation of a previously unknown cannabinoid, cannabizetol (CBGD, 7), from Cannabis sativa <\/em>extracts, representing the third member of the rare class of methylene-bridged dimeric cannabinoids.<\/p>\n\n\n\n

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Sustainable Synthesis of 1,2,3-Triazoles using Cyrene as a Biodegradable Solvent in Click Chemistry<\/strong><\/h2>\n\n\n\n
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ChemSusChem<\/em>, 2025<\/strong>
The first successful synthesis of 1,2,3-triazoles using Cyrene as a biodegradable and non-toxic solvent in click chemistry has been developed. Find out more here<\/a>.<\/p>\n\n\n\n

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PROTACs: Targeted Protein Degradation for Neurodegenerative and Cancer Targets<\/strong><\/h2>\n\n\n\n

We are developing innovative PROTACs to degrade disease-related proteins implicated in neurodegenerative disorders (e.g. tau protein, DASPO) and cancers (tubulin). These bifunctional molecules hijack the ubiquitin-proteasome system to selectively remove otherwise undruggable targets.<\/em><\/p>\n\n\n\n

Key publications: Pharmaceutics<\/em> 2023<\/strong>, 15<\/em>(5), 467; https:\/\/doi.org\/10.3390\/pharmaceutics15051467<\/a> BioRxiv<\/em> 2025<\/strong>, https:\/\/www.biorxiv.org\/content\/10.1101\/2025.05.22.655572v1<\/a><\/p>\n\n\n\n

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The project is coordinated by Prof. Passarella, member of the European research network ProteoCure<\/a><\/strong> – COST ACTION 20113.<\/h3>\n\n\n\n
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A Blood-Brain Barrier-permeable Guanylhydrazone analogue of the ASIC3 activator GMQ inhibits human Glioblastoma stem cell growth in Vitro<\/strong><\/h2>\n\n\n\n
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ChemMedChem, 2026<\/strong><\/em><\/p>\n\n\n\n

A Blood\u2013Brain Barrier\u2010Permeable Guanylhydrazone Analogue of the ASIC3 Activator GMQ Inhibits Human Glioblastoma Stem Cell Growth In Vitro (PNS) and activated by extracellular H , that is dysregulated in peripheral neuropathic pain. ASIC3 was found in stem cells of central nervous system (CNS)\u2013located glioblastoma multiforme (GBM CSCs), and its chronic activation kills dysfunctional GBM CSCs without any effect on ASIC3-lacking CNS tissues. We rationally designed and synthesized blood\u2013brain barrier (BBB)\u2013 compliant analogues of GMQ, a known guanidyl quinazoline ASIC3 activator; we replaced its guanidine group with a guanyl hydrazone (GH) and carried out scaffold substitutions and other structural variations in 16 GMQ analogues to establish a struc- ture\u2013activity relationship (SAR). Our more potent GH analogue 1a showed specific activity against GBM CSC neurospheres, coupled with a better safety profile on mammalian nontumor cells and a better brain-to-plasma ratio compared with GMQ. Such results provide valuable insights for further structural optimization of heteroaryl GHs as ASIC3 modulators.<\/p>\n\n\n\n

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Synthesis of Sulfonamides in the Biobased Solvent Cyrene<\/strong><\/h2>\n\n\n\n
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ChemistryOpen, 2026<\/strong><\/em><\/p>\n\n\n\n

An alternative and efficient protocol for sulfonamide synthesis using the biobased solvent Cyrene is reported. A broad range of amines reacts smoothly with sulfonyl chlorides at room temperature, furnishing 20 sulfonamides in moderate to high yields within 30\u201360 min. Products are isolated by simple precipitation without chromatography, while Cyrene can be recovered (up to 79%) and reused without loss of performance.<\/p>\n\n\n\n

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Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding<\/strong><\/h2>\n\n\n\n
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Organic letters, 2026<\/em><\/strong><\/p>\n\n\n\n

Benzoxaboroles, prominent scaffolds in medicinal chemistry, are typically modified on the benzene ring. In contrast, functionalization of the oxaborol ring is less common and often challenging. Indeed, 3-hydroxy-benzoxaboroles are virtually impossible to isolate due to their tautomeric equilibrium with the carbonyl form. In this work, we introduce a novel class of stereodefined 3-difluoromethyl-benzoxaboroles. The replacement of the hydroxy group with \u2212CHF2<\/sub> preserves stability while promoting bioactivity, owing to the lipophilic H-bond donor properties of the latter. Find out more here<\/a>.<\/p>\n\n\n\n

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Photochemical C4-Selective C\u2013H Amination of Quinolines via N<\/em>-Shift of Heteroaryl Azides<\/strong><\/h2>\n<\/div>\n\n\n\n
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Organic letters, 2026<\/em><\/strong><\/p>\n\n\n\n

We report a photochemical strategy enabling the direct synthesis of 3,4-diaminoazines through C3-to-C4 nitrogen migration (N<\/em>-shift). Blue LED irradiation of 3-azidoquinolines at room temperature allows C4-selective C\u2013H amination while concurrently installing diverse amines at the C3–<\/em>position. In contrast, N-<\/em>shifts in 3-azidopyridines preferentially form diazepines, reflecting divergent reactivity governed by N<\/em>-heterocycle electronics, as supported by computational analysis.<\/p>\n\n\n\n

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Safracin B as a Synthetic Linchpin: From Natural Product to Drug Intermediate and Beyond<\/strong><\/h2>\n\n\n\n
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Eur. J. Org. Chem., 2026<\/em><\/strong><\/p>\n\n\n\n

The reactivity of safracin B is investigated as a platform for the efficient synthesis of cyanosafracin B and safracin A, with particular emphasis on the optimization of reaction conditions to achieve high yield and purity. In addition, a complete assignment of the nuclear magnetic resonance spectra of these structurally complex members of the safracin family is reported. Overall, this study deepens the understanding of structure\u2013reactivity relationships within safracin natural products and highlights their value as versatile scaffolds for synthetic, analytical, and medicinal chemistry applications.<\/p>\n\n\n\n

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Synthesis of \u03b1-fluorocinnamate derivatives as novel cathepsin S inhibitors with in vitro antiproliferative activity against pancreatic cancer cells<\/strong><\/h2>\n\n\n\n
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Bioorg. Med. Chem.<\/strong><\/em><\/em>, 2025<\/strong>
We have designed and synthesized three new derivatives basing on an isosteric replacement (H\u2013F) at the level of cinnamate moiety. These derivatives emerged as potent covalent inhibitors of CatS (1.8\u20132.6 \u00b5M) with 2F<\/strong> showing also weak inhibition activity against CatL (20 %) and CatB (29 %). In vitro<\/em> assays of 2F<\/strong> against pancreatic cancer cell lines BXPC3 and CAPAN1 revealed significant antiproliferative activity, with IC50<\/sub> = 5.79 \u00b5M and 20.75 \u00b5M, respectively. To find out more details follow the page<\/a><\/p>\n\n\n\n

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\n\t\t\t\tRotational Motion in Bispidines: A Conformational Study<\/a>\n\t\t\t<\/h4>\n\t\t\t\t\t\t
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Organic Letters<\/em> 2025<\/strong>, DOI: 10.1021\/acs.orglett.5c02839<\/a><\/p>\n\n\n\n

Francesco Migliano, Luca Pozzi, Andrea Citarella, Giovanni Macetti, Leonardo Lo Presti, Daniele Passarella* and Valerio Fasano*<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t

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\n\t\t\t\tAsymmetric Total Synthesis of (\u2212)\u2010Glycybridin B, a Pharmacophore Screened Candidate for Tubulin Binding in Chemistry – A European Journal has the following publication status: Published Online<\/a>\n\t\t\t<\/h4>\n\t\t\t\t\t\t
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Chemistry – A European Journal<\/em> 2025<\/strong>, DOI: 10.1002\/chem.202502228<\/a><\/p>\n\n\n\n

Alice Maiocchi, Maxim Shevelev, Zlata Boiarska, Juan Est\u00e9vez-Gallego, Francesca Bonato, Paolo Orlando, Alessandra Chinosi, Emanuele Marcone, Andrea Citarella, Dragos Horvath, Michel O. Steinmetz, Andrea E. Prota, Alexandre Varnek, Valerio Fasano and Daniele Passarella<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t

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Journal of Medicinal Chemistry<\/em> 2025<\/strong>, DOI: 10.1021\/acs.jmedchem.5c00717<\/a><\/p>\n\n\n\n

Andrea Citarella, Silvia Belluti, Davide Bonanni, Davide Moi, Isabella Piccinini, Arianna Rinaldi, Chiara Papulino, Rosaria Benedetti, Laura Cuoghi, Stefano Di Ciolo, Alessandra Silvani, Lucia Altucci, Luca Pinzi, Silvia Franchini, Daniele Passarella, Claudia Sorbi, Clelia Giannini, Carol Imbriano, Giulio Rastelli<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t

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\n\t\t\t\tSynthesis and multitarget inhibitory effect of indole-based ethyl cinnamate derivatives against SARS-CoV-2 Mpro\u00a0and cathepsins for broad-spectrum anti-coronavirus activity<\/a>\n\t\t\t<\/h4>\n\t\t\t\t\t\t
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Bioorganic and Medicinal Chemistry<\/a> 2025, DOI: 10.1016\/j.bmc.2025.118258<\/a><\/p>\n\n\n\n

Andrea\u00a0Citarella,\u00a0Giulia\u00a0Sibille,\u00a0Davide\u00a0Moi,\u00a0Alessandro\u00a0Dimasi,\u00a0Tommaso\u00a0Braga,\u00a0Lorenzo Dal\u00a0Col,\u00a0Lorenzo\u00a0Ruberto,\u00a0Stefano\u00a0Pieraccini,\u00a0Maurizio\u00a0Sironi,\u00a0Nicola\u00a0Micale,\u00a0Tanja\u00a0Schirmeister,\u00a0Valerio\u00a0Fasano,\u00a0Alessandra\u00a0Silvani,\u00a0Clelia\u00a0Giannini,\u00a0Giorgio\u00a0Gribaudo,\u00a0Daniele\u00a0Passarella<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t

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\n\t\t\t\tDesign, synthesis and characterization of aryl bis-guanyl hydrazones as RNA binders of\u00a0C9orf72\u00a0G4C2\u00a0extended repeats<\/a>\n\t\t\t<\/h4>\n\t\t\t\t\t\t
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European Journal of Medicinal Chemistry<\/em>, 2025<\/strong>, 293<\/em>,\u00a0117736, DOI: 10.1016\/j.ejmech.2025.117736<\/a><\/p>\n\n\n\n

Alice\u00a0Maiocchi,\u00a0Martina\u00a0Pedrini,\u00a0Veronica\u00a0Ferrari,\u00a0Agata Sofia\u00a0Assun\u00e7ao Carreira,\u00a0Vincenzo Maria\u00a0D’Amore,\u00a0Federica\u00a0Santoro,\u00a0Anna\u00a0Di Porzio,\u00a0Maddalena\u00a0Bosetti,\u00a0Riccardo\u00a0Cristofani,\u00a0Alessandra\u00a0Silvani,\u00a0Diego\u00a0Brancaccio,\u00a0Luciana\u00a0Marinelli,\u00a0Francesco Saverio\u00a0Di Leva,\u00a0Alessandro\u00a0Provenzani,\u00a0Angelo\u00a0Poletti,\u00a0Pierfausto\u00a0Seneci<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t

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\n\t\t\t\tAutomated fluorine-18 radiolabeling via an alkyne\u2013azide cycloaddition reaction on a dual peptide-functionalized liposome surface for\u00a0in vivo\u00a0PET imaging<\/a>\n\t\t\t<\/h4>\n\t\t\t\t\t\t
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Frontiers in Pharmacology<\/em>, 2025<\/strong>, 16<\/em>, 1\u201316. DOI: 10.3389\/fphar.2025.1566257

Marco Iannone, Marcelo Kravicz, Paolo Rainone, Antonia I. Antoniou, Stefano Stucchi, Silvia Valtorta, Arianna Amenta, Elia Anna Turolla, Sara Pellegrino, Daniele Passarella, Elisa Vino, Sergio Todde, Francesca Re, Pierfausto Seneci, Rosa Maria Moresco<\/p>\n\t\t\t\t<\/div>\n\t\t\t\n\t\t\t\t\t\t\t\t\t<\/article>\n\t\t\t\t\t\t\t\t\t\t\t<\/div>\n\t\t\t<\/div>\n<\/div><\/section>\n\n\n\n

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Professor Daniele Passarella <\/h2><\/div>

Full Professor of Organic Chemistry<\/strong>
University of Milan \u2013 Department of Chemistry<\/strong>

Email: daniele.passarella@unimi.it<\/a><\/p><\/div><\/div>\n<\/div>\n\n\n\n

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Curriculum Vitae<\/a><\/div>\n<\/div>\n<\/div>\n<\/div><\/section>\n","protected":false},"excerpt":{"rendered":"

PassaLab Check out our latest publications! Dissecting Structural and Functional Determinants of Microtubules Stabilization through Guided Chemical Modulation J. Med. Chem.\u00a02026 Paclitaxel (PTX) is a widely used microtubule (MT) stabilizer whose clinical utility is limited by peripheral neuropathy, likely due to drug-induced structural perturbations of neuronal MTs. Here, we aimed to discern how taxane derivatives […]<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"_uag_custom_page_level_css":"","site-sidebar-layout":"no-sidebar","site-content-layout":"page-builder","ast-site-content-layout":"full-width-container","site-content-style":"unboxed","site-sidebar-style":"unboxed","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"disabled","ast-breadcrumbs-content":"","ast-featured-img":"disabled","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"disabled","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"set","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"class_list":["post-17","page","type-page","status-publish","hentry"],"uagb_featured_image_src":{"full":false,"thumbnail":false,"medium":false,"medium_large":false,"large":false,"1536x1536":false,"2048x2048":false},"uagb_author_info":{"display_name":"passalab","author_link":"https:\/\/sites.unimi.it\/passalab\/author\/passalab\/"},"uagb_comment_info":0,"uagb_excerpt":"PassaLab Check out our latest publications! Dissecting Structural and Functional Determinants of Microtubules Stabilization through Guided Chemical Modulation J. Med. Chem.\u00a02026 Paclitaxel (PTX) is a widely used microtubule (MT) stabilizer whose clinical utility is limited by peripheral neuropathy, likely due to drug-induced structural perturbations of neuronal MTs. Here, we aimed to discern how taxane derivatives…","_links":{"self":[{"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/pages\/17","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/comments?post=17"}],"version-history":[{"count":267,"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/pages\/17\/revisions"}],"predecessor-version":[{"id":27477,"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/pages\/17\/revisions\/27477"}],"wp:attachment":[{"href":"https:\/\/sites.unimi.it\/passalab\/wp-json\/wp\/v2\/media?parent=17"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}