Table · dataset · 2026
Fluorinated Aliphatic Thiols in the Design of Cephalosporin Conjugates for Metallo-β-Lactamase Inhibition
Listed in ZivaHub and Deakin Research Online and DMU Figshare — shown once because both records carry DOI 10.1021/acsomega.6c07917.s001
Antibiotic resistance is a major global health challenge, with the rapid spread of metallo-β-lactamase (MBL)-expressing bacteria presenting a serious clinical threat.
Description
In this study, we synthesized and investigated a series of novel cephalosporin conjugates envisioned to release MBL inhibitors upon MBL-mediated hydrolysis. The designed compounds consist of a cephalosporin core linked to trifluoromethylated aliphatic thiol-based MBL inhibitors.
Conjugates releasing aliphatic thiols upon hydrolysis by the New Delhi Metallo-β-lactamase-1 (NDM-1) were identified, confirming that fluorination improves the leaving group properties of some aliphatic thiols compared to a nonfluorinated control. However, when comparing with a conjugate containing an aromatic thiol, fluorinated aliphatic thiol release appeared slower and mechanistically more complex, thus incompletely resolved.
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The conjugates exhibited potent inhibitory activity against several subclass B1 MBLs. In addition, the utility of <sup>19</sup>F NMR as an alternative method for hydrolysis monitoring was exemplified. The findings highlight the potential, but also some unsolved challenges, of altering the leaving group ability of aliphatic thiol-based inhibitors to exploit the catalytic activity of NDM-1 for the selective release of inhibitors in MBL-producing bacteria.
Links
Where it is published
- DOI doi.org/10.1021/acsomega.6c07917.s001 ↗
DOI / persistent id · from zivahub uct ac za
Catalogue records · 1
- OAI-PMH record api.figshare.com/v2/oai?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Af… ↗
metadata API · from zivahub uct ac za
Topics
- From keywords
- Astronomy & Astrophysics · Astronomy & Astrophysics · Astronomy & Astrophysics · Cancer · Cancer · Cancer · Chemistry · Chemistry · Chemistry · Earth & Environmental Science · Earth & Environmental Science · Earth & Environmental Science · Immunology · Immunology · Immunology · Infectious diseases · Infectious diseases · Infectious diseases · Life Sciences · Life Sciences · Life Sciences · Medicine & Health · Medicine & Health · Medicine & Health · Microbiology · Microbiology · Microbiology
Provenance · 3 source records, 32 field assertions
| Source | Key | Last seen | Raw |
|---|---|---|---|
| ZivaHub | oai:figshare.com:article/34036718 | 12 d ago | JSON v1 |
| Deakin Research Online | oai:figshare.com:article/34036718 | 12 d ago | JSON v1 |
| DMU Figshare | oai:figshare.com:article/34036718 | 12 d ago | JSON v1 |
| Field | Assertion | Extractor | Evidence |
|---|---|---|---|
| access_level | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[disease].local:disease:cancer | mapping · figshare dmu ac uk | vocabulary-mapper@1.0.0 | keywords['Cancer'] |
| concepts[disease].local:disease:cancer | mapping · zivahub uct ac za | vocabulary-mapper@1.0.0 | keywords['Cancer'] |
| concepts[disease].local:disease:cancer | mapping · dro deakin edu au | vocabulary-mapper@1.0.0 | keywords['Cancer'] |
| concepts[field].anzsrc:field:320211 | mapping · figshare dmu ac uk | vocabulary-mapper@1.0.0 | keywords['Infectious Diseases'] |
| concepts[field].anzsrc:field:320211 | mapping · zivahub uct ac za | vocabulary-mapper@1.0.0 | keywords['Infectious Diseases'] |
| concepts[field].anzsrc:field:320211 | mapping · dro deakin edu au | vocabulary-mapper@1.0.0 | keywords['Infectious Diseases'] |
| concepts[field].anzsrc:group:3107 | mapping · dro deakin edu au | vocabulary-mapper@1.0.0 | keywords['Microbiology'] |
| concepts[field].anzsrc:group:3107 | mapping · figshare dmu ac uk | vocabulary-mapper@1.0.0 | keywords['Microbiology'] |
| concepts[field].anzsrc:group:3107 | mapping · zivahub uct ac za | vocabulary-mapper@1.0.0 | keywords['Microbiology'] |
| concepts[field].anzsrc:group:3204 | mapping · figshare dmu ac uk | vocabulary-mapper@1.0.0 | keywords['Immunology'] |
| concepts[field].anzsrc:group:3204 | mapping · zivahub uct ac za | vocabulary-mapper@1.0.0 | keywords['Immunology'] |
| concepts[field].anzsrc:group:3204 | mapping · dro deakin edu au | vocabulary-mapper@1.0.0 | keywords['Immunology'] |
| concepts[field].local:field:astronomy | mapping · figshare dmu ac uk | connector:figshare_dmu_ac_uk@1.0.0 | |
| concepts[field].local:field:astronomy | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:astronomy | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:chemistry | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:chemistry | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:chemistry | mapping · figshare dmu ac uk | connector:figshare_dmu_ac_uk@1.0.0 | |
| concepts[field].local:field:earth-environmental | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:earth-environmental | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:earth-environmental | mapping · figshare dmu ac uk | connector:figshare_dmu_ac_uk@1.0.0 | |
| concepts[field].local:field:life-sciences | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:life-sciences | mapping · figshare dmu ac uk | connector:figshare_dmu_ac_uk@1.0.0 | |
| concepts[field].local:field:life-sciences | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:medicine-health | mapping · dro deakin edu au | connector:dro_deakin_edu_au@1.0.0 | |
| concepts[field].local:field:medicine-health | mapping · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| concepts[field].local:field:medicine-health | mapping · figshare dmu ac uk | connector:figshare_dmu_ac_uk@1.0.0 | |
| description | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/description |
| license | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/rights |
| publication_date | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| title | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/title |