3-hydroxy-4-oxo-4h-pyran- or 3-hydroxy-4-oxo-1,4-dihydropyridine derivatives as protein-adhesive active substances

A method comprising contacting skin, hair and/or nails with a compound of the formula I,

• where
• E denotes NR5 or O,
• R1 denotes a UV chromophore, which is bonded via an O atom and renders the compound of the formula I capable of absorbing UV radiation in the range from 400 to 200 nm,
• R2, R3 or R4 each, independently of one another, denote —H, -A, —OA-, —(CH2)p—OH, —C(O)OA, COOH or COOX,
• p denotes an integer from 1 to 4,
• X is the counterion to the [COO−] group,
• R5 denotes A and
• A denotes alkyl having 1 to 20 C atoms and/or salts, tautomers, stereoisomers and/or solvates thereof, including mixtures thereof in all ratios, for protection of the skin, of the hair and/or of the nails against UV-induced damage.

Compounds of the formula I

• where
• E denotes NR5 or O,
• R1 is a substituent of the formula II, III, IV, V, VI, VII, VIII, IX, X, XI, XII, XIII, XIV or XV,
• where
• R1 to R14 each, independently of one another, denote —H, —OH, —OA, -A, —NH2, —NHA, —NA2, —NH—(CH2—CH2—O)n—H, —N[(CH2—CH2—O)n—H]2, —[NHA2]X, —[NA3]X, —SO3H, —[SO3]X, 2H-benzotriazol-2-yl- or
• n is an integer from 1 to 25,
• X is the counterion to the cations [NHA2]+ and [NA3]+ or the anion [SO3]− and
• Y and Z each, independently of one another, denote the structural unit I-1
• A, hydroxyl, —OA or —NH—C(CH3)3,
• W denotes —(CH2)m—O or —(CH2)o—C(O)—O and
• m and o each, independently of one another, denote an integer from 1 to 4,
• with the proviso that at least one substituent of the substituents R1 to R14 in the formulae II, III, IV, VII, X, XII and XV denotes
• OH, —OA, -A, —NH2, —NHA, —NA2, —NH—(CH2—CH2—O)n—H, —N[(CH2—CH2—O)n—H]2, —[NHA2]X, —[NA3]X, —SO3H, —[SO3]X, 2H-benzotriazol-2-yl- or
• R2, R3 or R4 each, independently of one another, denote —H, -A, —OA-, —(CH2)p—OH, —C(O)OA, COOH or COOX,
• p denotes an integer from 1 to 4,
• X is the counterion to the [COO−] group,
• R5 denotes A and
• A denotes alkyl having 1 to 20 C atoms,
• where the compounds 2-methyl-4-oxo-4H-pyran-3-yl (E)-3-(4-hydroxy-phenyl)-acrylate or 2-methyl-4-oxo-4H-pyran-3-yl 2-hydroxybenzoate are excluded.

A functionalized protein-containing matrix comprising a structural unit of the formula I-1

• in which R2, R3 or R4 each, independently of one another, denote —H, -A, —OA-, —(CH2)p—OH, —C(O)OA, COOH or COOX,
• p denotes an integer from 1 to 4,
• X is the counterion to the [COO−] group, and where
• E denotes NR5 or O,
• as linker functionalizing the protein-containing matrix, where the symbol * denotes the linking site in the form of a covalent single bond to a molecule which is intended to be adsorbed onto or covalently bonded to the matrix.