A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes

Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the preparation of nine folate conjugates of the tripyrrolic prodigiosene skeleton. T...

Descripción completa

Detalles Bibliográficos
Autores principales: Figliola, Carlotta, Marchal, Estelle, Groves, Brandon R., Thompson, Alison
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064012/
https://www.ncbi.nlm.nih.gov/pubmed/35519339
http://dx.doi.org/10.1039/c9ra01435g
_version_ 1784699274965024768
author Figliola, Carlotta
Marchal, Estelle
Groves, Brandon R.
Thompson, Alison
author_facet Figliola, Carlotta
Marchal, Estelle
Groves, Brandon R.
Thompson, Alison
author_sort Figliola, Carlotta
collection PubMed
description Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the preparation of nine folate conjugates of the tripyrrolic prodigiosene skeleton. The strict requirement for step-wise construction of the folate core is demonstrated, so as to achieve conjugation at only the desired γ-carboxylic acid and thus maintain the α-carboxylic site for folate receptor (FRα) recognition. Linkages via ethylenediamine, polyethylene glycol and glutathione are demonstrated.
format Online
Article
Text
id pubmed-9064012
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90640122022-05-04 A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes Figliola, Carlotta Marchal, Estelle Groves, Brandon R. Thompson, Alison RSC Adv Chemistry Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the preparation of nine folate conjugates of the tripyrrolic prodigiosene skeleton. The strict requirement for step-wise construction of the folate core is demonstrated, so as to achieve conjugation at only the desired γ-carboxylic acid and thus maintain the α-carboxylic site for folate receptor (FRα) recognition. Linkages via ethylenediamine, polyethylene glycol and glutathione are demonstrated. The Royal Society of Chemistry 2019-05-07 /pmc/articles/PMC9064012/ /pubmed/35519339 http://dx.doi.org/10.1039/c9ra01435g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Figliola, Carlotta
Marchal, Estelle
Groves, Brandon R.
Thompson, Alison
A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title_full A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title_fullStr A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title_full_unstemmed A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title_short A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
title_sort step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064012/
https://www.ncbi.nlm.nih.gov/pubmed/35519339
http://dx.doi.org/10.1039/c9ra01435g
work_keys_str_mv AT figliolacarlotta astepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT marchalestelle astepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT grovesbrandonr astepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT thompsonalison astepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT figliolacarlotta stepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT marchalestelle stepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT grovesbrandonr stepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes
AT thompsonalison stepwisesyntheticapproachisnecessarytoaccessgconjugatesoffolatefolateconjugatedprodigiosenes

Ejemplares similares