78974-67-1Relevant articles and documents
Photoactivated coumaryl-diazopyruvate fluorescent label for amine functional groups of tissues containing type-I collagen
Timberlake, George T.,Reddy, G. Kesava,Stehno-Bittel, Lisa,Weber, Joerg F.,Amslinger, Sabine,Givens, Richard S.
, p. 473 - 479 (2007/10/03)
The design, synthesis and application of a new fluorescent-labeling reagent for collagen has been developed as a prerequisite for the design of a photoactivated collagen-crosslinking compound for surgical wound closure. The amine groups in collagen are the targets of a rational design for a new fluorophore because natural collagen crosslinks are formed between primary (1°) amine groups of lysine and hydroxylysine. The availability of 1° amines for crosslinking in native collagenous tissues was evaluated by reacting tendon and corneal samples with o-phthalaldehyde and dansyl chloride, fluorophores commonly used for the detection of 1° and 2° amines. The resulting fluorescent collagen fibrils indicated the presence of amines in native tissue. Subsequently, a photoactivated fluorescent label for 1° and 2° amines, coumaryl gamma-amino-butyric acid diazopyruvate (CGDP), was designed and synthesized. CGDP was first used to photolabel poly-L-lysine, forming a fluorescent, covalent bond to the 1° amine. CGDP was then photoreacted with corneal and tendon tissue samples to produce CGDP fluorescent-labeled samples that were statistically significantly more fluorescent than were the controls. These experiments support the postulate that 1° or 2° (or both) amines in native collagenous tissues are available to serve as targets for photoactivated collagen crosslinkers for wound closure.