Selective Derivatization of Hexahistidine-Tagged Recombinant Proteins

Kadambar, Vasantha Krishna; Melman, Artem

doi:10.1007/978-3-030-15950-4_13

Cited by 2 publications

(3 citation statements)

References 91 publications

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“…[2] The developed strategies are usually based on the reactivity of side chain residues of lysine and cysteine containing amino or thiol groups, respectively. [1] In particular, N-hydroxysuccinimide (NHS) esters, [3] isocianate (or thioisocianate), [4] and aldehydes for reductive amination [5] represent the most relevant functional groups exploited in the attack of the amino residue of lysine, while maleimides, [6] and α-halocarbonyls [7] are the main electrophiles used for the functionalization of the nucleophilic group of cysteines. [8] In addition, novel synthetic procedures involving selective metal-catalysed or metal-directed reactions, have been optimized.…”

Section: Introductionmentioning

confidence: 99%

“…For example, most of the recent works have focused attention on the functionalization of proteins or antibodies, which can be used as drugs against cancer or infections [2] . The developed strategies are usually based on the reactivity of side chain residues of lysine and cysteine containing amino or thiol groups, respectively [1] . In particular, N ‐hydroxysuccinimide (NHS) esters, [3] isocianate (or thioisocianate), [4] and aldehydes for reductive amination [5] represent the most relevant functional groups exploited in the attack of the amino residue of lysine, while maleimides, [6] and α‐halocarbonyls [7] are the main electrophiles used for the functionalization of the nucleophilic group of cysteines [8] .…”

Section: Introductionmentioning

confidence: 99%

“…In the past decades, protein labeling has been widely used in research and industry for biosensing, diagnostic imaging, targeted drug delivery, and other applications. [1] For example, most of the recent works have focused attention on the functionalization of proteins or antibodies, which can be used as drugs against cancer or infections. [2] The developed strategies are usually based on the reactivity of side chain residues of lysine and cysteine containing amino or thiol groups, respectively.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A Facile Access to Green Fluorescent Albumin Derivatives

Saletti,

Paolino,

Venditti

et al. 2024

ChemBioChem

View full text Add to dashboard Cite

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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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Selective Derivatization of Hexahistidine-Tagged Recombinant Proteins

Cited by 2 publications

References 91 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

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