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. Author manuscript; available in PMC: 2019 Oct 15.
Published in final edited form as: Bioorg Med Chem. 2018 Apr 4;26(19):5280–5290. doi: 10.1016/j.bmc.2018.04.009

Figure 4. Photocleavage of the QC/nickel bis(dithiolene) adduct on a protein.

Figure 4

A) Lysines on bovine serum albumin (BSA) were capped via reaction with p-nitrophenyl quadricyclane carbonate 5. The resulting QC-BSA and untreated BSA (negative control) were treated with nickel bis(dithiolene) biotin 8 (50 μM in PBS) for 30 min to form adduct 13 or 8-treated BSA. The reactions were quenched with QCOAc and protein was purified from excess small molecule via centrifugal filtration with an Amicon Ultra 10 kDa molecular weight cutoff filter. 13 and 8-treated BSA in PBS were irradiated with a 365 nm handheld UV lamp for 0, 10, 30, or 60 min to cleave the adduct, providing 14 and 8. Protein products were separated from free 8 via centrifugal filtration as described above. C) Protein from Figure 4A was analyzed via western blot with an α-biotin-HRP antibody. Q = 13, B = 8-treated BSA.