Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants.

N-demethylation acid-base properties hapten immunotherapy microspeciation morphine skeleton nor-compounds protonation state vaccine

Journal

Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009

Informations de publication

Date de publication:
02 Sep 2020
Historique:
received: 07 08 2020
revised: 24 08 2020
accepted: 01 09 2020
entrez: 5 9 2020
pubmed: 6 9 2020
medline: 11 3 2021
Statut: epublish

Résumé

Vaccination could be a promising alternative warfare against drug addiction and abuse. For this purpose, so-called haptens can be used. These molecules alone do not induce the activation of the immune system, this occurs only when they are attached to an immunogenic carrier protein. Hence obtaining a free amino or carboxylic group during the structural transformation is an important part of the synthesis. Namely, these groups can be used to form the requisite peptide bond between the hapten and the carrier protein. Focusing on this basic principle, six nor-morphine compounds were treated with ethyl acrylate and ethyl bromoacetate, while the prepared esters were hydrolyzed to obtain the

Identifiants

pubmed: 32887468
pii: molecules25174009
doi: 10.3390/molecules25174009
pmc: PMC7504778
pii:
doi:

Substances chimiques

Analgesics, Opioid 0
Esters 0
Haptens 0
Protons 0
Morphine 76I7G6D29C

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Magyar Tudományos Akadémia
ID : János Bolyai Research Scholarship
Organisme : Ministry for Innovation and Technology
ID : UNKP-19-4-SE-28
Organisme : National Research, Development and Innovation Office, Hungary
ID : NKFIH KH-130401
Organisme : National Research, Development and Innovation Office, Hungary
ID : VEKOP-2.3.3-15-2017-00020
Organisme : Emberi Eroforrások Minisztériuma
ID : 1783-3/2018/FEKUTSRAT

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Auteurs

István Köteles (I)

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., H-1092 Budapest, Hungary.

Károly Mazák (K)

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., H-1092 Budapest, Hungary.

Gergő Tóth (G)

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., H-1092 Budapest, Hungary.
Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, H-1117 Budapest, Hungary.

Boglárka Tűz (B)

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., H-1092 Budapest, Hungary.

Sándor Hosztafi (S)

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., H-1092 Budapest, Hungary.

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Classifications MeSH