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US 9,540,405 B2Granted
Diaminophenothiazinium derivatives for labelling biomolecules, method and substrate for labelling oligonucleotides, and oligonucleotides obtained
AssigneesUniversite Claude Bernard Lyon I, Centre National De La Recherche Scientifique
InventorsCarole Chaix, Gabriel De Crozals
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Abstract
The present invention relates to diaminophenothiazinium derivatives of formula (I); in which R1, R2, R3, R4, R5, R6 and X− are as defined in Claim 1, and also the methods for labelling oligonucleotides using such a derivative, labeling substrates and the oligonucleotides which can be obtained by means of such methods or from such labelling substrates.
Claims19
Diaminophenothiazinium derivatives of formula (I):
- in which:
- one of the R1, R2, R3 and R4 groups represents -A1-OR7, with A1 representing a linear or branched alkylene chain comprising from 2 to 12 carbons, the oxygen and nitrogen atoms being separated by at least two consecutive carbon atoms, and R7 representing a group forming, with OA1 to which it is bonded, a phosphoramidite, phosphodiester, or a hydrogen phosphonate group,
- the other R1, R2, R3 and R4 groups, which may be identical or different, represent, independently of one another:
- an -A2-OR8 group, with A2 representing a linear or branched alkylene chain comprising from 2 to 12 carbons, the oxygen and nitrogen atoms being separated by at least two consecutive carbon atoms, and R8 representing a member selected from the group consisting of trityl, 4-O-monomethoxytrityl, 4,4′-O-dimethoxytrityl, tert-butyldimethylsilyl, acetyl, trifluoroacetyl, 9-phenylxanthen-9-yl, and fluorenylmethyloxycarbonyl,
- an alkyl group having from 2 to 12 carbon atoms,
- or, R1 and R2 or R3 and R4 are bonded to one another to form, with the nitrogen atom to which they are bonded, a piperidinyl or pyrrolidinyl group,
- R5 and R6, which may be identical or different, represent, independently of one another, a hydrogen, chlorine, bromine, iodine or fluorine atom, or an alkyl group having from 1 to 12 carbon atoms, an alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 12 carbon atoms, an acyl group or a phenyl group, and
- X− represents an anion.
5 more elements
An oligonucleotide synthesis substrate comprising at least one diaminophenothiazinium derivative covalently grafted at the surface according to the series:
- in which:
- R5, R6, which may be identical or different, represent, independently of one another, a hydrogen, chlorine, bromine, iodine, or fluorine atom, or an alkyl group having from 1 to 12 carbon atoms, an alkenyl group having from 2 to 12 carbon atoms, an alkynly group having from 2 to 12 carbon atoms, an acyl group, or a phenyl group,
- X− represents an anion,
- R′1 and R′2 , identical or different, represent, independently of one another, an alkyl group having from 2 to 12 carbon atoms, or R1 and R2 are bonded to one another to form, with the nitrogen atom to which they are bonded, a piperidinyl or pyrrolidinyl group,
- A1′ and A1″, which may be identical or different, represent, independently of one another, a linear or branched alkylene chain comprising from 2 to 12 carbons, and
- R9 represents a member selected from the group consisting of trityl, 4-O-monomethoxytrityl, 4, 4′-O-dimethoxytrityl, tert-butyldimethylsilyl, acetyl, trifluoroacetyl, 9-phenylxanthen-9-yl, and fluorenylmethyloxycarbonyl;
- and
- R10 represents —CO-A3-CO—NH-Substrate, with A3 representing a linear or branched alkylene chain comprising from 1 to 6 carbon atoms;
- or
- in which:
- R5, R6, which may be identical or different, represent, independently of one another, a hydrogen, chlorine, bromine, iodine or fluorine atom, or an alkyl group having from 1 to 12 carbon atoms, alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 12 carbon atoms, an acyl group or a phenyl group,
- X− represents an anion,
- R′2 and R′4, which may be identical or different, represent, independently of one another, and alkyl group having from 2 to 12 carbon atoms,
- A1′ and A1″ , which may be identical or different, represent, independently of one another, a linear or branched alkylene chain comprising from 2 to 12 carbons, and
- R9 represents a member selected from the group consisting of trityl, 4-O-monomethoxytrityl, 4, 4′-O-dimethoxytrityl, tert-butyldimethylsilyl, acetyl, trifluoroacetyl, 9-phenylxanthen-9-yl, and fluorenylmethyloxycarbonyl;
- and
- R10 represents —CO-A3-CO—NH-Substrate, with A3 representing a linear or branched alkylene chain comprising from 1 to 6 carbon atoms.
14 more elements
Dependencies are inferred from the claim text.