@entity16377 (PACs) are secondary plant metabolites that mediate nonenzymatic collagen cross-linking and enhance the properties of collagen based tissue, such as dentin. The extent and nature of cross-linking is influenced by the composition and specific chemical structure of the bioactive compounds present in certain PAC-rich extracts. This study investigated the effect of the molecular weight and stereochemistry of @entity3978 compounds on two important properties of dentin, biomechanics, and biostability. For that, purified @entity11572 , a @entity10418 , and some of its derivatives were selected: PAC dimers (A1, A2, B1, and B2) and a trimer (C1), @entity11676 (Ga), its esters @entity68337 (MGa) and @entity8394 ( @entity6987 ), and a pentagalloyl ester of @entity413 ( @entity22216 ). Synergism was assessed by combining the most active PAC and @entity11676 derivative. Mechanical properties of dentin organic matrix were determined by the modulus of elasticity obtained in a flexural test. Biostability was evaluated by the resistance to collagenase degradation. PACs significantly enhanced dentin mechanical properties and decreased collagen digestion. Among the @entity11676 derivatives, only @entity22216 had a significant enhancing effect. The lack of observed C1: @entity22216 synergy indicates that both compounds have similar mechanisms of interaction with the dentin matrix. These findings reveal that the molecular weight of @entity6398 have a determinant effect on their interaction with type I collagen and modulates the mechanism of cross-linking at the molecular, intermolecular, and inter-microfibrillar levels.

Mimicking the hierarchical functions of dentin collagen cross-links with plant derived XXXX and phenolic acids.

@entity16377 :: ('MESH:D044945', 'Chemical') :: ['Proanthocyanidins'] @entity3978 :: ('CHEBI:26195', 'Chemical') :: ['polyphenol'] @entity6987 :: ('MESH:D011454', 'Chemical') :: ['PGa'] @entity11572 :: ('MESH:D010636', 'Chemical') :: ['phenols'] @entity8394 :: ('MESH:D011435', 'Chemical') :: ['propyl-gallate'] @entity10418 :: ('MESH:C017616', 'Chemical') :: ['phenolic acid'] @entity68337 :: ('MESH:C052082', 'Chemical') :: ['methyl-gallate'] @entity6398 :: ('MESH:D059808', 'Chemical') :: ['polyphenols'] @entity413 :: ('MESH:D005947', 'Chemical') :: ['glucose'] @entity11676 :: ('MESH:D005707', 'Chemical') :: ['gallic acid'] @entity22216 :: ('MESH:D011462', 'Chemical') :: ['PGG']
@entity11572 :: (MESH:D010636,Chemical) :: ['phenols']
