Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid
Copyright © 2017 Elsevier Masson SAS. All rights reserved..
The series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella pneumoniae ATCC 700603 (ESBL), Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus MRSA ATCC 43300, Staphylococcus aureus MSSA ATCC 25923. Peptide derivatives proved to be the most versatile ones, their MIC values relative to most strains was lower than MPA alone. It has been noted that the activity of amino acid derivatives depends on the configuration at the chiral center in the amino acid unit and methyl esters indicated better antimicrobial activity than analogs with free carboxylic group.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2018 |
|---|---|
| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:143 |
|---|---|
| Enthalten in: |
European journal of medicinal chemistry - 143(2018) vom: 01. Jan., Seite 646-655 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Siebert, Agnieszka [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Amino Acids |
|---|
| Anmerkungen: |
Date Completed 10.01.2018 Date Revised 31.03.2024 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.ejmech.2017.11.094 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM278816371 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM278816371 | ||
| 003 | DE-627 | ||
| 005 | 20240331231918.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2018 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.ejmech.2017.11.094 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1358.xml |
| 035 | |a (DE-627)NLM278816371 | ||
| 035 | |a (NLM)29216563 | ||
| 035 | |a (PII)S0223-5234(17)30997-2 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Siebert, Agnieszka |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid |
| 264 | 1 | |c 2018 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 10.01.2018 | ||
| 500 | |a Date Revised 31.03.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2017 Elsevier Masson SAS. All rights reserved. | ||
| 520 | |a The series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella pneumoniae ATCC 700603 (ESBL), Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus MRSA ATCC 43300, Staphylococcus aureus MSSA ATCC 25923. Peptide derivatives proved to be the most versatile ones, their MIC values relative to most strains was lower than MPA alone. It has been noted that the activity of amino acid derivatives depends on the configuration at the chiral center in the amino acid unit and methyl esters indicated better antimicrobial activity than analogs with free carboxylic group | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Amino acids | |
| 650 | 4 | |a Antimicrobial activity | |
| 650 | 4 | |a Mycophenolic acid | |
| 650 | 4 | |a Peptides | |
| 650 | 4 | |a Tuftsin | |
| 650 | 7 | |a Amino Acids |2 NLM | |
| 650 | 7 | |a Anti-Bacterial Agents |2 NLM | |
| 650 | 7 | |a Peptides |2 NLM | |
| 650 | 7 | |a Mycophenolic Acid |2 NLM | |
| 650 | 7 | |a HU9DX48N0T |2 NLM | |
| 700 | 1 | |a Wysocka, Magdalena |e verfasserin |4 aut | |
| 700 | 1 | |a Krawczyk, Beata |e verfasserin |4 aut | |
| 700 | 1 | |a Cholewiński, Grzegorz |e verfasserin |4 aut | |
| 700 | 1 | |a Rachoń, Janusz |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t European journal of medicinal chemistry |d 1994 |g 143(2018) vom: 01. Jan., Seite 646-655 |w (DE-627)NLM106608835 |x 1768-3254 |7 nnns |
| 773 | 1 | 8 | |g volume:143 |g year:2018 |g day:01 |g month:01 |g pages:646-655 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.ejmech.2017.11.094 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 143 |j 2018 |b 01 |c 01 |h 646-655 | ||