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View article: Bifunctional Photocatalysts Display Proximity-Enhanced Catalytic Activity in Metallaphotoredox C–O Coupling
Bifunctional Photocatalysts Display Proximity-Enhanced Catalytic Activity in Metallaphotoredox C–O Coupling Open
Dual catalytic reactions may be made more effective through improved integration of the catalytic cycles achieved using bifunctional catalysts. Herein, we describe two bifunctional photocatalysts consisting of a photoactive donor-acceptor …
View article: Bifunctional photocatalysts display proximity-enhanced catalytic activity in metallaphotoredox C–O coupling
Bifunctional photocatalysts display proximity-enhanced catalytic activity in metallaphotoredox C–O coupling Open
Dual catalytic reactions may be made more effective through an improved integration of the catalytic cycles achieved using bifunctional catalysts. Herein we describe new bifunctional photocatalysts consisting of a photoactive donor-accepto…
View article: Amine‐Carbamate Self‐Immolative Spacers Counterintuitively Release 3° Alcohol at Much Faster Rates than 1° Alcohol Payloads
Amine‐Carbamate Self‐Immolative Spacers Counterintuitively Release 3° Alcohol at Much Faster Rates than 1° Alcohol Payloads Open
Self‐immolative (SI) spacers are degradable chemical connectors widely used in prodrugs and drug conjugates to release pharmaceutical ingredients in response to specific stimuli. Amine‐carbamate SI spacers are particularly versatile, as th…
View article: Ex vivo mass spectrometry-based biodistribution analysis of an antibody-Resiquimod conjugate bearing a protease-cleavable and acid-labile linker
Ex vivo mass spectrometry-based biodistribution analysis of an antibody-Resiquimod conjugate bearing a protease-cleavable and acid-labile linker Open
Immune-stimulating antibody conjugates (ISACs) equipped with imidazoquinoline (IMD) payloads can stimulate endogenous immune cells to kill cancer cells, ultimately inducing long-lasting anticancer effects. A novel ISAC was designed, featur…
View article: Visible Light-Promoted β-Functionalization of Carbonyl Compounds in the Presence of Organic Dyes
Visible Light-Promoted β-Functionalization of Carbonyl Compounds in the Presence of Organic Dyes Open
Herein, we investigate the use of organic photocatalysts in the visible light-promoted β-functionalization of carbonyl compounds. In particular, we studied the addition of aliphatic aldehydes to α,β-unsaturated compounds (β-Michael additio…
View article: RGD Cyclopeptide Equipped with a Lysine‐Engaging Salicylaldehyde Showing Enhanced Integrin Affinity and Cell Detachment Potency
RGD Cyclopeptide Equipped with a Lysine‐Engaging Salicylaldehyde Showing Enhanced Integrin Affinity and Cell Detachment Potency Open
Salicylaldehyde (SA) derivatives are emerging as useful fragments to obtain reversible‐covalent inhibitors interacting with the lysine residues of the target protein. Here the SA installation at the C terminus of an integrin‐binding cyclop…
View article: Metallaphotoredox C−O and C−N Cross‐Coupling Using Donor‐Acceptor Cyanoarene Photocatalysts
Metallaphotoredox C−O and C−N Cross‐Coupling Using Donor‐Acceptor Cyanoarene Photocatalysts Open
Herein we report a study on the use of donor‐acceptor cyanoarenes as photocatalysts for C−O and C−N coupling reactions promoted by nickel. We found that some of these stable and readily available organic compounds can replace the precious …
View article: Advanced Pyrrolidine‐Carbamate Self‐Immolative Spacer with Tertiary Amine Handle Induces Superfast Cyclative Drug Release
Advanced Pyrrolidine‐Carbamate Self‐Immolative Spacer with Tertiary Amine Handle Induces Superfast Cyclative Drug Release Open
Amine‐carbamate self‐immolative (SI) spacers represent practical and versatile tools in targeted prodrugs, but their slow degradation mechanism limits drug activation at the site of disease. We engineered a pyrrolidine‐carbamate SI spacer …
View article: Development and Biochemical Characterization of Self-Immolative Linker Containing GnRH-III-Drug Conjugates
Development and Biochemical Characterization of Self-Immolative Linker Containing GnRH-III-Drug Conjugates Open
The human gonadotropin releasing hormone (GnRH-I) and its sea lamprey analogue GnRH-III specifically bind to GnRH receptors on cancer cells and can be used as targeting moieties for targeted tumor therapy. Considering that the selective re…
View article: Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex
Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex Open
The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason…
View article: Celebrating Franco Cozzi's 70th Birthday
Celebrating Franco Cozzi's 70th Birthday Open
On the occasion of the 70th birthday of Franco Cozzi (Università degli Studi di Milano), a selection of articles by his friends, colleagues, and former students, who are among the leading researchers in the field of Organic Chemistry in It…
View article: Functionalized 2‐Hydroxybenzaldehyde‐PEG Modules as Portable Tags for the Engagement of Protein Lysine ϵ‐Amino Groups
Functionalized 2‐Hydroxybenzaldehyde‐PEG Modules as Portable Tags for the Engagement of Protein Lysine ϵ‐Amino Groups Open
The formation of reversible‐covalent interactions between a small‐molecule ligand and its protein target is emerging as a general strategy to design binders with increased affinity. In this context, 2‐hydroxybenzaldehyde (2HB) has been rec…
View article: A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages
A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages Open
The enzymatic dephosphorylation of a self-immolative spacer accelerates cargo release and acts as an additional and independent trigger in protease-sensitive prodrugs.
View article: Multimeric Presentation of RGD Peptidomimetics Enhances Integrin Binding and Tumor Cell Uptake
Multimeric Presentation of RGD Peptidomimetics Enhances Integrin Binding and Tumor Cell Uptake Open
The use of multimeric ligands is considered as a promising strategy to improve tumor targeting for diagnosis and therapy. Herein, tetrameric RGD (Arg‐Gly‐Asp) peptidomimetics were designed to target α v β 3 integrin‐expressing tumor cells.…
View article: Recent Catalytic Applications of (Cyclopentadienone)iron Complexes
Recent Catalytic Applications of (Cyclopentadienone)iron Complexes Open
(Cyclopentadienone)iron complexes (CICs) are attractive pre‐catalysts due to their easy preparation and robustness, which are uncommon features in homogeneous iron catalysis. They represent a striking example of how deeply a non‐innocent l…
View article: Fast Cyclization of a Proline‐Derived Self‐Immolative Spacer Improves the Efficacy of Carbamate Prodrugs
Fast Cyclization of a Proline‐Derived Self‐Immolative Spacer Improves the Efficacy of Carbamate Prodrugs Open
Self‐immolative (SI) spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a ( S )‐2‐(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticanc…
View article: Frontispiece: Innovative Linker Strategies for Tumor‐Targeted Drug Conjugates
Frontispiece: Innovative Linker Strategies for Tumor‐Targeted Drug Conjugates Open
Improvement of the pharmacological effects of cytotoxic agents with a concomitant decrease of systemic toxicity has been investigated for decades in order to reduce the side effects of tumor-targeting drugs. In their Review article, A. Dal…
View article: Innovative Linker Strategies for Tumor‐Targeted Drug Conjugates
Innovative Linker Strategies for Tumor‐Targeted Drug Conjugates Open
The covalent conjugation of potent cytotoxic agents to either macromolecular carriers or small molecules represents a well‐known approach to increase the therapeutic index of these drugs, thus improving treatment efficacy and minimizing si…
View article: Conjugates of Cryptophycin and RGD or <i>iso</i>DGR Peptidomimetics for Targeted Drug Delivery
Conjugates of Cryptophycin and RGD or <i>iso</i>DGR Peptidomimetics for Targeted Drug Delivery Open
RGD‐cryptophycin and iso DGR‐cryptophycin conjugates were synthetized by combining peptidomimetic integrin ligands and cryptophycin, a highly potent tubulin‐binding antimitotic agent across lysosomally cleavable Val‐Ala or uncleavable link…
View article: Rational Design of Antiangiogenic Helical Oligopeptides Targeting the Vascular Endothelial Growth Factor Receptors
Rational Design of Antiangiogenic Helical Oligopeptides Targeting the Vascular Endothelial Growth Factor Receptors Open
Tumor angiogenesis, essential for cancer development, is regulated mainly by vascular endothelial growth factors (VEGFs) and their receptors (VEGFRs), which are overexpressed in cancer cells. Therefore, the VEGF/VEGFR interaction represent…
View article: Synthesis and Biological Evaluation of RGD and <i>iso</i>DGR–Monomethyl Auristatin Conjugates Targeting Integrin α<sub>V</sub>β<sub>3</sub>
Synthesis and Biological Evaluation of RGD and <i>iso</i>DGR–Monomethyl Auristatin Conjugates Targeting Integrin α<sub>V</sub>β<sub>3</sub> Open
This work reports the synthesis of a series of small‐molecule–drug conjugates containing the α V β 3 ‐integrin ligand cyclo [DKP‐RGD] or cyclo [DKP‐ iso DGR], a lysosomally cleavable Val‐Ala (VA) linker or an “uncleavable” version devoid o…
View article: The Importance of Detail: How Differences in Ligand Structures Determine Distinct Functional Responses in Integrin α<sub>v</sub>β<sub>3</sub>
The Importance of Detail: How Differences in Ligand Structures Determine Distinct Functional Responses in Integrin α<sub>v</sub>β<sub>3</sub> Open
Ligand‐based control of protein functional motions can provide novel opportunities in the study of fundamental biological mechanisms and in the development of novel therapeutics. In this work we addressed the ligand‐based modulation of int…
View article: A dimeric bicyclic RGD ligand displays enhanced integrin binding affinity and strong biological effects on U-373 MG glioblastoma cells
A dimeric bicyclic RGD ligand displays enhanced integrin binding affinity and strong biological effects on U-373 MG glioblastoma cells Open
AC2-symmetric dimeric bicyclic integrin ligand, bearing two RGD motifs, displays enhanced biological effects compared to monovalent RGD analogues.
View article: CCDC 1885148: Experimental Crystal Structure Determination
CCDC 1885148: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: β-Glucuronidase triggers extracellular MMAE release from an integrin-targeted conjugate
β-Glucuronidase triggers extracellular MMAE release from an integrin-targeted conjugate Open
A non-internalizing conjugate targeting αvβ3 integrin inhibits the proliferation of integrin-expressing cancer cells in the presence of β-glucuronidase.
View article: Neutrophil Elastase Promotes Linker Cleavage and Paclitaxel Release from an Integrin‐Targeted Conjugate
Neutrophil Elastase Promotes Linker Cleavage and Paclitaxel Release from an Integrin‐Targeted Conjugate Open
This work takes advantage of one of the hallmarks of cancer, that is, the presence of tumor infiltrating cells of the immune system and leukocyte‐secreted enzymes, to promote the activation of an anticancer drug at the tumor site. The pept…
View article: Improving C=N Bond Reductions with (Cyclopentadienone)iron Complexes: Scope and Limitations
Improving C=N Bond Reductions with (Cyclopentadienone)iron Complexes: Scope and Limitations Open
Herein, we broaden the application scope of (cyclopentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre‐catalyst 1b , which is more active than the “Knölker complex” ( 1a ) and other members of its family, has bee…
View article: Synthesis and Biological Evaluation of Paclitaxel Conjugates Involving Linkers Cleavable by Lysosomal Enzymes and α<sub>V</sub>β<sub>3</sub>‐Integrin Ligands for Tumor Targeting
Synthesis and Biological Evaluation of Paclitaxel Conjugates Involving Linkers Cleavable by Lysosomal Enzymes and α<sub>V</sub>β<sub>3</sub>‐Integrin Ligands for Tumor Targeting Open
Two cyclo [DKP‐RGD]‐PTX (PTX = paclitaxel) and two cyclo [RGDfK]‐PTX conjugates containing the Gly‐Phe‐Leu‐Gly (GFLG) linker, which is cleavable by lysosomal enzymes, were synthesized and compared to two cyclo [DKP‐RGD]‐Val‐Ala‐PTX conjuga…
View article: Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting
Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting Open
RGD-α-amanitin and isoDGR-α-amanitin conjugates were synthesized by joining integrin ligands to α-amanitin via various linkers and spacers. The conjugates were evaluated for their ability to inhibit biotinylated vitronectin binding to the …