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• W2080486158 abstract "New thiolytically cleavable dithiobenzyl (DTB) urethane-linked conjugates of methoxypoly(ethylene glycol) (mPEG) and a model protein, lysozyme, were prepared and thoroughly characterized. In contrast to our earlier communication [Zalipsky, et al. (1999) Bioconjugate Chem. 10, 703], in the current study we used a more sterically hindered form of para-DTB urethane linkage containing a methyl group on the α-carbon to the disulfide moiety. The new reagent for covalent attachment of mPEG-DTB to amino groups of proteins was synthesized via a seven-step process. As a result of PEG conjugation, the lysozyme was shown to completely lose its bacterial cell wall-lysing activity. However, activity was almost fully restored upon cysteine-mediated cleavage of the PEG component. The conjugate decomposition process was monitored by RP-HPLC and by ion spray LC-MS, which showed the formation of the p-mercaptobenzyl urethane–lysozyme intermediate, and ultimately its conversion to the unmodified lysozyme as the sole protein component. Pharmacokinetic evaluation of 125I-labeled cleavable and noncleavable PEG-lysozyme given intravenously in rats revealed similar clearance patterns; both cleared in a significantly slower manner compared to that of the native protein. However, subcutaneous administration of the same conjugates showed a significantly larger AUC of the cleavable conjugate, indicating that some cleavage of the DTB urethane may have occurred. Although the DTB-linked PEG-lysozyme exhibited almost the same plasma clearance as the noncleavable counterpart, hinting that methyl-DTB linkage might be stable in the bloodstream, SDS–PAGE examination of the conjugate incubated in plasma showed decomposition at least partially mediated by albumin. These results suggest the potential of PEG-DTB-proteins as macromolecular prodrugs capable of generating fully active native proteins under in vivo conditions." @default.
• W2080486158 created "2016-06-24" @default.
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• W2080486158 date "2007-10-13" @default.
• W2080486158 modified "2023-10-14" @default.
• W2080486158 title "Thiolytically Cleavable Dithiobenzyl Urethane-Linked Polymer–Protein Conjugates as Macromolecular Prodrugs: Reversible PEGylation of Proteins" @default.
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• W2080486158 doi "https://doi.org/10.1021/bc7001902" @default.
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