Back to results
US 2017/0210700 A1Published application
3-aryl propiolonitrile compounds for thiol labeling
AssigneesUniversite De Strasbourg, Centre National De La Recherche Scientifique
InventorsALAIN WAGNER, OLEKSANDR KONIEV
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.
Claims7
Process for the preparation of a labeled compound comprising a thiol moiety, comprising contacting a compound comprising a thiol moiety with a compound of formula (I):
- wherein each of R1 to R5 is independently selected in the group consisting of:
- hydrogen atoms,
- alkyl, alkene or alkyne groups, optionally interrupted by at least one heteroatom selected among O, N and S,
- aryl groups,
- alkoxy groups,
- halogen atoms,
- amino (—NRR′) groups, wherein R and R′ are independently hydrogen atoms, alkyl, alkene, alkyne or aryl groups,
- hydroxylamine (—ONH2) group,
- hydrazine (—NH—NH2) group,
- nitro (—NO2) group,
- azido (—N3) group,
- diazonium (—N2+) group,
- maleimide group,
- alkyl- or aryl-carboxyl (—C(═O)OR) groups,
- alkyl- or aryl-carbonyl (—C(═O)R) groups,
- hydroxyl (—OH) group,
- boronic acid —B(OR″)2 group, wherein R″ is a hydrogen atom or an alkyl group,
- phosphine or phosphonium groups,
- isocyanate (—N═C═O) or isothiocyanate (—N═C═S) group,
- chlorosulfonyl (—SO2Cl) group,
- a —O—C(═O)—C(N2)—CF3 group or a —C(═O)—C(N2).CF3 group,
- activated esters, such as —C(═O)—NHS, perfluorinated esters and acylureas,
- a —C≡C—C≡N group,
- tags, and
- alkyl groups substituted by at least one of the previously listed groups, alternatively, two of R1 to R5 may form together and with the carbon atoms of the phenyl ring to which they are linked a mono or polycyclic ring, and
- wherein at least one of R1 to R5 comprises a tag moiety, selected from the group consisting of chemical groups appropriate for allowing one or several of the following:
- detection of the compound,
- vectorization of an agent of interest by the compound,
- solubilization of the compound,
- stabilization of the compound,
- improvement of the extraction and/or purification of the compound,
- modification of at least one of the ADME (Administration Distribution Metabolisation Excretion) parameters of the compound;
- addition of bioactivity to the compound;
- and
- addition of an appropriate functionality for click-chemistry.
32 more elements
Compound of the formula (II):
- wherein each of R1 to R5 is selected independently in the group consisting of:
- hydrogen atoms,
- alkyl, alkene or alkyne groups, optionally interrupted by at least one heteroatom selected among O, N and S,
- aryl groups,
- alkoxy groups,
- halogen atoms,
- amino (—NRR′) groups, wherein R and R′ are independently hydrogen atoms, alkyl, alkene, alkyne or aryl groups,
- hydroxylamine (—ONH2) group,
- hydrazine (—NH—NH2) group,
- nitro (—NO2) group,
- azido (—N3) group,
- diazonium (—N2+) group,
- maleimide group,
- alkyl- or aryl-carboxyl (—C(═O)OR) groups,
- alkyl- or aryl-carbonyl (—C(═O)R) groups,
- hydroxyl (—OH) group,
- boronic —B(OR″)2 group, wherein R″ is a hydrogen atom or an alkyl group,
- phosphine or phosphonium groups,
- isocyanate (N═C═O) or isothiocyanate (—N═C═S) group,
- chlorosulfonyl (—SO2C1) group,
- a O—C(═O)—C(N2)—CF3 group or a —C(═O)—C(N2)CF3 group,
- activated esters, such as —C(═O)—NHS, perfluorinated esters and acylureas,
- tags, and
- alkyl groups substituted by at least one of the previously listed groups,
- alternatively, two of R1 to R5 may form together and with the carbon atoms of the phenyl ring to which they are linked a mono or polycyclic ring, and
- wherein at least one of R1 to R5 comprises a maleimide, NHS-ester, azide or alkyne moiety.
23 more elements
Compound of formula (II):
- wherein each of R1 to R5 is selected independently in the group consisting of:
- hydrogen atoms,
- alkyl, alkene or alkyne groups, optionally interrupted by at least one heteroatom selected among O, N and S,
- aryl groups,
- alkoxy groups,
- halogen atoms,
- amino (—NRR′) groups, wherein R and R′ are independently hydrogen atoms, alkyl, alkene, alkyne or aryl groups,
- hydroxylamine (—ONH2) group,
- hydrazine (—NH—NH2) group,
- nitro (—NO2) group,
- azido (—N3) group,
- diazonium (—N2+) group,
- maleimide group,
- alkyl- or aryl-carboxyl (—C(═O)OR) groups,
- alkyl- or aryl-carbonyl (—C(═O)R) groups,
- hydroxyl (—OH) group,
- boronic —B(OR″)2 group, wherein R″ is a hydrogen atom or an alkyl group,
- phosphine or phosphonium groups,
- isocyanate (N═C═O) or isothiocyanate (—N═C═S) group,
- chlorosulfonyl (—SO2Cl) group,
- a O—C(═O)—C(N2)—CF3 group or a —C(═O)—C(N2)CF3 group,
- activated esters, such as —C(═O)—NHS, perfluorinated esters and acylureas,
- tags, and
- alkyl groups substituted by at least one of the previously listed groups, alternatively two of R1 to R5 may form together and with the carbon atoms of the phenyl ring to which they are linked a mono or polycyclic ring, and
- wherein at least one of R1 to R5 is bonded to a compound of interest selected from the group consisting of a fluorophore, a group of atoms comprising at least one radioactive atom, a group of atoms of known mass, a ligand, a drug, a therapeutic agent, a biomolecule, a DNA fragment, a nanoobject, or a support.
22 more elements
Dependencies are inferred from the claim text.