Sulfonate Version of OHPAS Linker Has Two Distinct Pathways of Breakdown: Elimination Route Allows Para-Hydroxy-Protected Benzylsulfonate (PHP-BS) to Serve as an Alternative Self-Immolative Group
In: Bioconjugate Chemistry, Jg. 31 (2020-03-25), S. 1392-1399
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Zugriff:
Recently we have reported that the ortho-hydroxy-protected aryl sulfate (OHPAS) system can be exploited as a new self-immolative group (SIG) for phenolic payloads. We extended the system to nonphenolic payloads by simply introducing a para-hydroxy benzyl (PHB) spacer. As an additional variation of the system, we explored a benzylsulfonate version of the OHPAS system and found that it has two distinct breakdown pathways, cyclization and 1,4-elimination, the latter of which implies that para-hydroxy-protected (PHP) benzylsulfonate (BS) can also be used as an alternative SIG. The PHP-BS system was found to be stable chemically and in mouse and human plasma, having payload release rates comparable to those of the original OHPAS conjugates.
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Sulfonate Version of OHPAS Linker Has Two Distinct Pathways of Breakdown: Elimination Route Allows Para-Hydroxy-Protected Benzylsulfonate (PHP-BS) to Serve as an Alternative Self-Immolative Group
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Autor/in / Beteiligte Person: | Song, Jina ; Hyang Sook Lee ; Seo, Beomseok ; Kim, Sun-Young ; Park, Suho ; Seo, Donghoon ; Park, Okku ; Jung, Doohwan ; Cho, Jongun ; Yun, Sanghyeon ; Lee, Jaeho ; Jihyeon, Ha ; Lee, Sangkwang ; Seol, Minah ; Tae Kyo Park ; Sena, Kim |
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Zeitschrift: | Bioconjugate Chemistry, Jg. 31 (2020-03-25), S. 1392-1399 |
Veröffentlichung: | American Chemical Society (ACS), 2020 |
Medientyp: | unknown |
ISSN: | 1520-4812 (print) ; 1043-1802 (print) |
DOI: | 10.1021/acs.bioconjchem.0c00116 |
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