Photoswitchable compounds and affinity ligands, and their use for the optical control of affinity matrices

Photoswitchable azobiaryl compound according to formula (I)

• wherein:
• R1 and R1′ are independently selected from the group comprising H, F, Cl, Br, (CH2),CH3, CH((CH2)nCH3)((CH2)xCH3),C((CH2),CH3)((CH2)xCH3)((CH2) 2CH3), (CH2),CH((CH2)xCH3)—((CH2)zCH3), (CH2),C((CH2)xCH3)((CH2)yCH3)((CH2)zCH3), O(CH2)nCH3, OCH((CH2)nCH3)((CH2)xCH3), OC((CH2),CH3)—((CH2)xCH3)((CH2)zCH3), O(CH2),CH((CH2)xCH3)((CH2)zCH3),O(CH2),C((CH2)xCH3)((CH2)yCH3)((CH2) 2CH3), S(CH2),CH3, SCH((CH2)nCH3)((CH2)xCH3), SC((CH2) CH3)((CH2)xCH3)((CH2) 2CH3), S(CH2),CH((CH2)xCH3)((CH2)zCH3), S(CH2) DC((CH2)xCH3)((CH2)yCH3)((CH2)zCH3), NH2, NH(CH2),CH3, NHCH((CH2)nCH3)—((CH2)xCH3), NHC((CH2)n CH3)((CH2)xCH3)((CH2)zCH3), NH(CH2),CH((CH2)xCH3)((CH2)zCH3), NH(CH2) DC—((CH2)xCH3)—((CH2)yCH3)((CH2)zCH3), N((CH2),CH3)2, N(CH((CH2)nCH3)((CH2)xCH3))2, N(C((CH2)n,CH3)—((CH2)xCH3)((CH2)zCH3))2, N((CH2)nCH((CH2)xCH3)((CH2)zCH3))2, N((CH2)nC((CH2)xCH3)((CH2)yCH3)—((CH2)zCH3))2, aziridin-1-yl, azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, azepan-1-yl, azocan-1yl, morpholin-1-yl, 4-methyl-piperazin-1-yl,
• wherein n may be any integer from 0 to 10,
• wherein x may be any integer from 0 to 10,
• wherein y may be any integer from 0 to 10, and
• wherein z may be any integer from 0 to 10;
• wherein at least one of R1 or R1′ is not H;
• R2 and R2′ are independently selected from the group comprising SO3H, SO3Li, SO3Na, SO3K, COOH, COONHS, CONH2, CONH—(CH2)nCH3, CONH—((CH2)nCH3)((CH2)zCH3), CONH—(CH2)nSO3H, CONH—(CH2)nSO3Li, CONH—(CH2)nSO3Na, CONH—(CH2)nSO3K, CONH—(CH2)nCCH, CONH—(CH2)nN3, CONH—(CH2)nNH2, CONH—(CH2)nCOOH, CONH—(CH2)nNHAcI, CONH—(CH2)nNHAcBr, CONH—(CH2)nNHAcCl, CONH—(CH2)n N(maleimide), CONH—(CH2)n—NH(2-chloromethyl acrylate), CONH—(CH2)n—NH(vinylsulfonate), CONH—(CH2)n—NHCOPhF5, CONH—(CH2)n—NHSO2PhF5, CONH—(CH2)nCOONHS, CONH-PEG-OH, CONH-PEG-NH2, CONH-PEG-COOH, CONH-PEG-COONHS, CONH-PEG-O(CH2)nSO3H, CONH-PEG-O(CH2)nSO3Li, CONH-PEG-O(CH2)nSO3Na, CONH-PEG-O(CH2)nSO3K, CONH—PEG-NHAcI, CONH-PEG-NHAcBr, CONH-PEG-NHAcCl, CONH-PEG-N(maleimide), CONH-PEG-NH(2-chloromethyl acrylate), CONH-PEG-NH(vinylsulfonate), CONH-PEG-NHCOPhF5, CONH-PEG-NHSO2PhF5, CONH-PEG-N3, CONH-PEG-OCH2CCH, CONH-PEG-NHCH2CCH, CONH-PEG-N(CH2CCH)2, CONH-PEG-NHCO(CH2)nCOOH, CONH-PEG-NHCO(CH2)nCOONHS, CONH—(Xaa)n-OH, CONH—(Xaa)n-NH(CH2)nSO3H, CONH—(Xaa)n-NH(CH2) SO3Li, CONH—(Xaa),—NH(CH2)nSO3Na, CONH—(Xaa)n-NH(CH2)nSO3K, CONH—(Xaa)n-OMe, CONH—(Xaa)n-ONHS, CONH—(Xaa)n-ONHS, CONH—(Xaa)n-NH(CH2)nCCH, CONH—(Xaa)n-NH(CH2)nN3, CONH—(Xaa)n-NH(CH2)zNHAcI, CONH—(Xaa)n-NH(CH2)zNHAcBr, CONH—(Xaa)n-NH(CH2)zNHAcCl, CONH—(Xaa)n-NH(CH2)z—N(maleimide), CONH—(Xaa)n-NH(CH2)zNH(2-chloromethyl acrylate), CONH—(Xaa)n-NH(CH2)zNH(vinylsulfonate), CONH—(Xaa)n-NH(CH2)zNHCOPhF5, CONH—(Xaa)n-NH(CH2)zNHSO2PhF5, CONH—(Xaa)n-N3, CONH—(Xaa)n-OCH2CCH, CONH—(Xaa)n-NHCH2CCH, CONH—(Xaa)n-N(OCH2CCH)2, CONH—(Xaa)n-NH—(CH2)nCOOH, CONH—(Xaa)n-NH—(CH2)nCOONHS, CONH—(Xaa)-NH-PEG-OH, CONH—(Xaa)n-NH-PEG-NH2, CONH—(Xaa)n-NH-PEG-COOH, CONH—(Xaa)n-NH-PEG-COONHS, CONH—(Xaa)n-NH-PEG-NHAcI, CONH—(Xaa)n-NH-PEG-NHAcBr, CONH—(Xaa)n-NH-PEG-NHAcCl, CONH—(Xaa)n-NH-PEG-N(maleimide), CONH—(Xaa)nNH-PEG-NH(2-chloromethyl acrylate), CONH—(Xaa)n-NH-PEG-NH(vinylsulfonate), CONH—(Xaa)n-NH-PEG-NHCOPhF5, CONH—(Xaa)n-NH-PEG-NHSO2PhF5, CONH—(Xaa)n-NH-PEG-N3, CONH—(Xaa)n-NH-PEG-OCH2CCH, CONH—(Xaa)n-NH-PEG-NHCH2CCH, CONH—(Xaa)n-NH-PEG-N(CH2CCH)2, CONH—(Xaa)n-NH-PEG-NHCO(CH2)nCOOH, CONH—(Xaa)n-NH-PEG-NHCO(CH2)nCOONHS,
• wherein Xaa can be any canonical or non-canonical amino acid,
• wherein n may be any integer from 0 to 10, and
• wherein z may be any integer from 0 to 10;
• R3 and R3′ are independently selected from the group comprising H, NH2, NHCO(C1-C6-alkyl), NHCO(C1-C6-haloalkyl),NHBoc, NHCbz, NHalloc, NH(CH2)nCH3, NHCH((CH2) CH3)((CH2)xCH3), NHC((CH2)n CH3)((CH2)xCH3)((CH2)zCH3), NH(CH2)nCH((CH2)xCH3)((CH2)zCH3), NH(CH2)nC((CH2)xCH3)((CH2)yCH3)((CH2) 2CH3), N((CH2)n CH3)2, N(CH((CH2)nCH3)—((CH2)xCH3))2, N(C((CH2)nCH3)((CH2)xCH3)((CH2) 2CH3))2, N((CH2) CH((CH2)xCH3)—((CH2)zCH3))2, N((CH2)nC((CH2)xCH3)((CH2)yCH3)((CH2)zCH3))2, aziridin-1-yl, azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, azepan-1-yl, azocan-1yl, morpholin-1-yl, 4-methyl-piperazin-1-yl, NHCH2CHCH2, N(CH2CHCH2)2, NHCH2CCH, N(CH2CCH)2, NHCOCCH, NHCO(CH2)nN3, NHacrylate, NH(2-chloromethyl acrylate), NH(vinyl sulfonate), N(maleimide), N(2-bromomaleimide), N(2,3-dibromomaleimide), NHCOaryl, NHCOhaloaryl, NHSO2aryl, NHSO2haloaryl, (CH2)nN(maleimide), (CH2)nN(2-bromomaleimide), (CH2)nN(2,3-dibromomaleimide), NHCO(CH2)nN(maleimide), NHCO(CH2)nN(2-bromomaleimide), NHCO(CH2)nN(2,3-dibromomaleimide), NCS, NCO, NH(CH2)nCH(O)CH2, N((CH2)nCH(O)CH2)2, NAcCH2CH(O)CH2,
• wherein n may be any integer from 0 to 10, and wherein z may be any integer from 0 to 10.