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Covalently Linked Protein Regulators02:04

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Proteins can undergo many types of post-translational modifications, often in response to changes in their environment. These modifications play an important role in the function and stability of these proteins. Covalently linked molecules include functional groups, such as methyl, acetyl, and phosphate groups, and also small proteins, such as ubiquitin. There are around 200 different types of covalent regulators that have been identified.
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Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
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Histone Modification02:32

Histone Modification

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The histone proteins have a flexible N-terminal tail extending out from the nucleosome. These histone tails are often subjected to post-translational modifications such as acetylation, methylation, phosphorylation, and ubiquitination. Particular combinations of these modifications form “histone codes” that influence the chromatin folding and tissue-specific gene expression.
Acetylation
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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Reversible lysine modification on proteins by using functionalized boronic acids.

Pedro M S D Cal1, Raquel F M Frade1, Carlos Cordeiro2

  • 1Research Institute for Medicines and Pharmaceutical Sciences (iMed.UL), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon (Portugal), Fax: (+351) 217946470.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 23, 2015
PubMed
Summary
This summary is machine-generated.

Iminoboronates enable bioorthogonal chemistry on proteins, allowing for reversible PEGylation of insulin and in situ assembly of a potent folic acid/paclitaxel drug conjugate. This versatile chemistry shows promise in bioconjugation and targeted cancer therapy.

Keywords:
boronic acidsconjugationcycloadditiondrug designprotein modifications

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Sequence-specific Labeling of Nucleic Acids and Proteins with Methyltransferases and Cofactor Analogues
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Area of Science:

  • Organic Chemistry
  • Bioconjugation Chemistry
  • Medicinal Chemistry

Background:

  • Bioorthogonal chemistry allows for selective reactions in biological systems.
  • Iminoboronates offer a versatile platform for chemical modifications.
  • Protein modification is crucial for developing new therapeutics and diagnostics.

Purpose of the Study:

  • To demonstrate the utility of iminoboronates in installing bioorthogonal handles on proteins.
  • To explore the application of iminoboronates in drug conjugation and modification of biomolecules.
  • To evaluate the efficacy and safety of iminoboronate-assembled drug conjugates.

Main Methods:

  • Utilized iminoboronates to introduce azide and alkyne functionalities onto proteins.
  • Applied iminoboronates for polyethylene glycol (PEG) conjugation to insulin.
  • Assembled a folic acid/paclitaxel small-molecule/drug conjugate in situ using iminoboronates.

Main Results:

  • Successfully installed azide and alkyne bioorthogonal functions on proteins.
  • Achieved reversible PEGylation of insulin, sensitive to fructose.
  • Developed a folic acid/paclitaxel conjugate with potent anti-cancer activity (IC50 = 20.7 nM) against NCI-H460 cells.
  • Demonstrated negligible cytotoxicity against CRL-1502 non-cancer cells.

Conclusions:

  • Iminoboronates are effective reagents for bioorthogonal functionalization of proteins.
  • Iminoboronate chemistry enables reversible modification of biomolecules like insulin.
  • In situ assembly of drug conjugates using iminoboronates shows significant therapeutic potential with high specificity.