Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe
A new chloroquine-derived photoaffinity probe has been prepared by a convergent synthesis from derivative of 4,7-dichloroquinoline and N1,N1-diethyl-N4-methylpentane. The features of this probe are a unique 3-azido photolabel, the pyridine ring of the quinoline, and the presence of a secondary amine...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/5/1084 |
| _version_ | 1797264082143805440 |
|---|---|
| author | Benita Kapuku D. Scott Bohle |
| author_facet | Benita Kapuku D. Scott Bohle |
| author_sort | Benita Kapuku |
| collection | DOAJ |
| description | A new chloroquine-derived photoaffinity probe has been prepared by a convergent synthesis from derivative of 4,7-dichloroquinoline and N1,N1-diethyl-N4-methylpentane. The features of this probe are a unique 3-azido photolabel, the pyridine ring of the quinoline, and the presence of a secondary amine at the 4-position of the quinoline. These features, particularly the 4-amino methylation, prevent triazole formation through combination of the 3-azide and the 4-amine. This undergoes facile cleavage with exposure to a medium-pressure mercury lamp with a 254 nm excitation wavelength. Trapping of the nitrene byproduct is accomplished with its reaction with N-phenylmaleimide as its cycloazidation product. The structure of a ring-opened DBU amine has been structurally characterized. |
| first_indexed | 2024-04-25T00:23:14Z |
| format | Article |
| id | doaj.art-594eb0f7292f42e7a5c0c32643fe3ffe |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-25T00:23:14Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-594eb0f7292f42e7a5c0c32643fe3ffe2024-03-12T16:51:00ZengMDPI AGMolecules1420-30492024-02-01295108410.3390/molecules29051084Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity ProbeBenita Kapuku0D. Scott Bohle1Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, QC H3A 0B8, CanadaDepartment of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, QC H3A 0B8, CanadaA new chloroquine-derived photoaffinity probe has been prepared by a convergent synthesis from derivative of 4,7-dichloroquinoline and N1,N1-diethyl-N4-methylpentane. The features of this probe are a unique 3-azido photolabel, the pyridine ring of the quinoline, and the presence of a secondary amine at the 4-position of the quinoline. These features, particularly the 4-amino methylation, prevent triazole formation through combination of the 3-azide and the 4-amine. This undergoes facile cleavage with exposure to a medium-pressure mercury lamp with a 254 nm excitation wavelength. Trapping of the nitrene byproduct is accomplished with its reaction with N-phenylmaleimide as its cycloazidation product. The structure of a ring-opened DBU amine has been structurally characterized.https://www.mdpi.com/1420-3049/29/5/1084antimalarialdrug targetphotoaffinity label |
| spellingShingle | Benita Kapuku D. Scott Bohle Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe Molecules antimalarial drug target photoaffinity label |
| title | Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe |
| title_full | Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe |
| title_fullStr | Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe |
| title_full_unstemmed | Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe |
| title_short | Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe |
| title_sort | synthesis and photolysis properties of a new chloroquine photoaffinity probe |
| topic | antimalarial drug target photoaffinity label |
| url | https://www.mdpi.com/1420-3049/29/5/1084 |
| work_keys_str_mv | AT benitakapuku synthesisandphotolysispropertiesofanewchloroquinephotoaffinityprobe AT dscottbohle synthesisandphotolysispropertiesofanewchloroquinephotoaffinityprobe |