Photochemical cross-linking of proteins with visible-light-absorbing 1,8-naphthalamides

Millard M. Judy; James Lester Matthews; Richard L. Boriak; A. Burlacu; David E. Lewis; Ronald E. Utecht

doi:10.1117/12.147669

7 July 1993 Photochemical cross-linking of proteins with visible-light-absorbing 1,8-naphthalamides

Millard M. Judy, James Lester Matthews, Richard L. Boriak, A. Burlacu, David E. Lewis, Ronald E. Utecht

Proceedings Volume 1882, Laser-Tissue Interaction IV; (1993) https://doi.org/10.1117/12.147669
Event: OE/LASE'93: Optics, Electro-Optics, and Laser Applications in Scienceand Engineering, 1993, Los Angeles, CA, United States

Abstract

We have newly synthesized a class of photochemical 1,8-naphthalimide dyes. Photochemical investigation strongly suggests that these dyes function as photoalkylation agents following activation to an intermediate state by visible light (circa 420 nm) excitation. The activated species reacts readily with nucleophilic amino acid residues, e.g., tryptophan, cysteine, and methionine. One dye, 1,14-bis-(N-hexyl-3'-bromo-1,8'-naphthalimid-4'-yl)-1,4,11,14- tetraazatetradecane-5,10-dione, which incorporates two reactive 1,8-naphthalimide groups at each end of an intervening structural bridge has been used to cross-link the protein monomers of F-actin, thus preventing its natural depolymerization at low salt concentrations, and to cross-link Apolipoprotein I of human high-density lipoprotein. These observations suggest continued study of these dyes as agents for protein cross-linking, tissue bonding, and inactivation of infectious agents.

Citation Download Citation

Millard M. Judy, James Lester Matthews, Richard L. Boriak, A. Burlacu, David E. Lewis, and Ronald E. Utecht "Photochemical cross-linking of proteins with visible-light-absorbing 1,8-naphthalamides", Proc. SPIE 1882, Laser-Tissue Interaction IV, (7 July 1993); https://doi.org/10.1117/12.147669

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