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

Millard M. Judy, James L. Matthews, R. L. Boriack, A. Burlacu, D. E. Lewis,

Research output: Chapter in Book/Report/Conference proceedingConference contribution

19 Scopus citations


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.

Original languageEnglish (US)
Title of host publicationProceedings of SPIE - The International Society for Optical Engineering
PublisherPubl by Society of Photo-Optical Instrumentation Engineers
Number of pages4
ISBN (Print)0819411094, 9780819411099
StatePublished - 1993
EventLaser-Tissue Interaction IV - Los Angeles, CA, USA
Duration: Jan 18 1993Jan 20 1993

Publication series

NameProceedings of SPIE - The International Society for Optical Engineering
ISSN (Print)0277-786X


OtherLaser-Tissue Interaction IV
CityLos Angeles, CA, USA

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Computer Science Applications
  • Applied Mathematics
  • Electrical and Electronic Engineering


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