A tri(ethylene glycol)-tethered Morita–Baylis–Hillman dimer in the formation of macrocyclic crown ether-paracyclophane hybrid structures

Saletti, Mario; Venditti, Jacopo; Paolino, Marco; Zacchei, Arianna; Giuliani, Germano; Giorgi, Gianluca; Bonechi, Claudia; Donati, Alessandro; Cappelli, Andrea

doi:10.1039/d3ra06792k

Cited by 4 publications

(1 citation statement)

References 19 publications

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“…[18][19][20] Furthermore, the fluorogens showing aggregation induced emission (AIE) features (i. e. emission intensities higher in the solid state than in solution) [21] display higher sensitivity, accuracy, and photostability when compared to traditional fluorescence probes, which are emissive in solution but often undergoes to aggregation caused quenching (ACQ) processes at high concentration. [22,23] Some Morita-Baylis-Hillman derivatives (i. e. 1, Figure 1) have been recently developed in our laboratories to react with imidazole [24] or n-butylammine [25] leading to cinnamic derivatives (i. e. 2). showing fluorogenic properties.…”

Section: Introductionmentioning

confidence: 99%

A Facile Access to Green Fluorescent Albumin Derivatives

Saletti,

Paolino,

Venditti

et al. 2024

ChemBioChem

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A Morita‐Baylis‐Hillman Adduct (MBHA) derivative bearing a triphenylamine moiety was found to react with human serum albumin (HSA) shifting its emission from the blue to the green‐yellow thus leading to green fluorescent albumin (GFA) derivatives and enlarging the platform of probes for aggregation‐induced fluorescent‐based detection techniques. A possible interaction of MBHA derivative 7 with a lipophilic pocket within the HSA structure was suggested by docking studies. DLS experiments showed that the reaction with HSA induce a conformational change of the protein contributing to the aggregation process of GFA derivatives. The results of investigations on the biological properties suggested that GFA retained the ability of binding drug molecules such as warfarin and diazepam. Finally, cytotoxicity evaluation studies suggested that, although the MBHA derivative 7 at 0.1 µg/mL affected the percentage of cell viability in comparison to the negative control, it cannot be considered cytotoxic, whereas at all the other concentrations ≥ 0.5 µg/mL resulted cytotoxic at different extent.

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Section: Introductionmentioning

confidence: 99%

A Facile Access to Green Fluorescent Albumin Derivatives

Saletti,

Paolino,

Venditti

et al. 2024

ChemBioChem

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Reactivity of a Morita–Baylis–Hillman Adduct Derivative Bearing a Triphenylamine Moiety with Lysine Models

Venditti,

Saletti,

Paolino

et al. 2024

Chemistry An Asian Journal

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The reactivity of Morita‐Baylis‐Hillman Adduct (MBHA) derivative 7 was studied with different primary amine derivatives such as n‐butylamine, Na‐acetyl‐L‐lysine methyl ester, and a poly‐(L‐lysine) derivative as lysine models to obtain information about the possible reactions in complex protein environments. MBHA derivative 7 reacted with n‐butylamine or Na‐acetyl‐L‐lysine methyl ester producing monoadducts 9a or 9c, which showed bright emission features in the green region at 526‐535 nm with photoluminescence quantum yield values in solutions of 73% and 51%, respectively. Based on these results, MBHA derivative 7 can be considered an interesting new fluorogenic probe potentially useful in the labelling of basic amino acid residues. Furthermore, similar to other MBHA derivatives, compound 7 showed the tendency to produce diadducts especially in polar solvents system where specific interactions between the extended aromatic moieties may play a major role.

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Preparation of Light‐responsive Unnatural RNA Bases via a Chromogenic Morita‐Baylis‐Hillman Adduct Path

Lami,

Barneschi,

Saletti

et al. 2024

ChemPhotoChem

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RNA‐based tools for biological and pharmacological research are raising an increasing interest. Among these, RNA aptamers whose biological activity can be controlled via illumination with specific wavelengths represent an important target. Here, we report on a proof‐of‐principle study supporting the viability of a systematic use of Morita‐Baylis‐Hillman adducts (MBHAs) for the synthesis of light‐responsive RNA building blocks. Accordingly, a specific acetylated MBHA derivative was employed in the functionalization of the four natural RNA bases as well as two unnatural bases (5‐aminomethyl uracil and 5‐methylaminomethyl uracil). The results reveal a highly selective functionalization for both unnatural bases. The conjugation products were then investigated spectroscopically, photochemically and computationally. It is shown that when a single light‐responsive unit is present (i.e. when using 5‐methylaminomethyl uracil), the generated unnatural uracil behaves like a cinnamic‐framework‐based photochemical switch that isomerizes upon illumination through a biomimetic light‐induced intramolecular charge transfer mechanism driving a barrierless and, therefore, ultrafast reaction path.

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A tri(ethylene glycol)-tethered Morita–Baylis–Hillman dimer in the formation of macrocyclic crown ether-paracyclophane hybrid structures

Abstract: A tri(ethylene glycol)-tethered MBHA dimer was synthesized and found to react with n-butylamine leading to the formation of macrocyclic crown ether-paracyclophane hybrid structures that could be modulated by light.

Cited by 4 publications

References 19 publications

A Facile Access to Green Fluorescent Albumin Derivatives

A Facile Access to Green Fluorescent Albumin Derivatives

Reactivity of a Morita–Baylis–Hillman Adduct Derivative Bearing a Triphenylamine Moiety with Lysine Models

Preparation of Light‐responsive Unnatural RNA Bases via a Chromogenic Morita‐Baylis‐Hillman Adduct Path

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