biostudies-literatureCencer MU.S. Environmental Protection AgencyNational Institute of General Medical SciencesNIGMS NIH HHS404-10https://www.ebi.ac.uk/biostudies/studies/S-EPMC4294588biostudies-literatureUnknown16(1)Dopamine mimics the exceptional moisture-resistant adhesive properties of the amino acid, DOPA, found in adhesive proteins secreted by marine mussels. The catechol side chain of dopamine was functionalized with a nitro-group, and the effect of the electron withdrawing group modification on the cross-linking chemistry and bioadhesive properties of the adhesive moiety was evaluated. Both nitrodopamine and dopamine were covalently attached as a terminal group onto an inert, 4-armed poly(ethylene glygol) (PEG-ND and PEG-D, respectively). PEG-ND and PEG-D exhibited different dependence on the concentration of NaIO4 and pH, which affected the curing rate, mechanical properties, and adhesive performance of these biomimetic adhesives differently. PEG-ND cured instantly and its bioadhesive propertiBiomacromoleculesEffect of nitro-functionalization on the cross-linking and bioadhesion of biomimetic adhesive moiety.PMC4294588GM104846R15 GM104846R15GM104846Liu YCencer MMurley MLee BPfalseEffect of nitro-functionalization on the cross-linking and bioadhesion of biomimetic adhesive moiety.Dopamine mimics the exceptional moisture-resistant adhesive properties of the amino acid, DOPA, found in adhesive proteins secreted by marine mussels. The catechol side chain of dopamine was functionalized with a nitro-group, and the effect of the electron withdrawing group modification on the cross-linking chemistry and bioadhesive properties of the adhesive moiety was evaluated. Both nitrodopamine and dopamine were covalently attached as a terminal group onto an inert, 4-armed poly(ethylene glygol) (PEG-ND and PEG-D, respectively). PEG-ND and PEG-D exhibited different dependence on the concentration of NaIO4 and pH, which affected the curing rate, mechanical properties, and adhesive performance of these biomimetic adhesives differently. PEG-ND cured instantly and its bioadhesive properti2015-01-01T00:00:00Z2015 Jan2025-05-29T21:22:17.74Z2025-05-29T21:22:17.74ZS-EPMC42945882549504310.1021/bm5016333