Self-immolative systems

Patent metadata

Field	Value
Publication number	US-12110307-B2
Application number	US-201917280240-A
Country	US
Kind code	B2
Filing date	Oct 29, 2019
Priority date	Oct 30, 2018
Publication date	Oct 8, 2024
Grant date	Oct 8, 2024

Abstract

The present invention is concerned with self-immolative recognition and/or responsive systems for electrophilic compounds, especially alkylating agents, which systems may comprise disclosure or detection of the alkylating agent. The present invention is especially concerned with non-protic triggered self-immolative systems, molecules, and methods, and in particular for detection of non-protic electrophilic agents, and especially alkylating agents, for example alkyl or benzylic halides, which may be found in pesticides or fumigants, or chemical warfare agents.

First claim

The invention claimed is:

1. A self-immolative molecule suitable to be triggered by non-protic electrophilic agents, having structural formula:

wherein Nu is phosphorus (P), R 1 and R 2 comprise phenyl functional groups or substituted phenyl functional groups, and releasable portion is a chemical moiety capable of generating a detection/measurable response upon release.

2. The self-immolative molecule according to claim 1 , wherein the detection/measurable response is generation of a colour or fluorescence.

3. The self-immolative molecule according to claim 1 , comprising multiple releasable portions.

4. The self-immolative molecule according to claim 1 , having structural formula:

wherein Nu is P, R 1 and R 2 comprise phenyl functional groups or substituted phenyl functional groups, and R 4 , R 5 , R 6 , R 7 and R 8 comprise between 0-3 methyl (CH 3 ) groups and at least 1 nitro (NO 2 ) group, with the remainder being hydrogen (H) atoms.

5. The self-immolative molecule according to claim 4 , wherein R 6 is NO 2 , and R 4 , R 6 , R 7 and R 8 are H.

6. The self immolative molecule according to claim 1 , having the structural formula:

wherein Nu is P, R 1 and R 2 comprise phenyl functional groups or substituted phenyl functional groups, and R 4 , R 5 , R 6 , R 7 and R 8 comprise at least 2 self-immolative portions, each linked to at least one releasable portion.

7. A self-immolative triggered method for interrogating a sample suspected of comprising a non-protic electrophilic agent comprising contacting the sample, in the presence of a mild base, with a self-immolative molecule suitable to be triggered by non-protic electrophilic agents, wherein the self-immolative molecule comprises at least one trigger portion linked to at least one releasable portion via a self-immolative portion, and wherein the self-immolative molecule has a structural formula:

wherein Nu is phosphorus (P) and R 1 and R 2 comprise phenyl functional groups or substituted phenyl functional groups.

8. The self-immolative triggered method according to claim 7 , wherein R 1 and/or R 2 comprise phenyl functional groups.

9. The self-immolative triggered method according to claim 8 , wherein the releasable portion is a chemical moiety capable of generating a detection/measurable response upon release.

10. The self-immolative triggered method according to claim 7 , wherein the non-protic electrophilic agent is an alkylating agent.

11. The self-immolative triggered method according to claim 7 , wherein the mild base is diisopropylethylamine.

12. The self-immolative triggered method according to claim 7 , wherein the sample is further contacted with the self-immolative molecule in the presence of an iodide salt.

Assignees

• Secr Defence

Inventors

• Russell Andrew
• Hayes Wayne Cord
• Sambrook Mark Rodney
• Leroux Flavien
• Acton Aaron
• Feula Antonio
• Gavriel Alexander Gabriel

Classifications

• C07F9/70

  Organo-arsenic compounds · CPC title

• C07F9/5442

  Aromatic phosphonium compounds (P-C aromatic linkage) · CPC title

• C07F9/5022 Primary

  Aromatic phosphines (P-C aromatic linkage) · CPC title

• A62D3/30

  by reacting with chemical agents · CPC title

• G01N31/22

  using chemical indicators (G01N31/02 takes precedence) · CPC title