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@ARTICLE{Wittenburg:302999,
author = {S. Wittenburg and M. R. Zuleeg and K. Peter and P.
Lemnitzer and R. Voget and A. Bricelj and M. Gobec and N.
Dierlamm and M. B. Braun and T. M. Geiger and C. Heim and A.
Stakemeier and K. G. Wagner and R. P. Nowak and M. D.
Hartmann and I. Sosič and M. Gütschow and J. Krönke$^*$
and C. Steinebach},
title = {{E}nhancing {S}olubility in {VHL}-{B}ased {PROTAC}s:
{O}ptimized {USP}7 {D}egraders for {I}mproved
{D}evelopability.},
journal = {Journal of medicinal chemistry},
volume = {68},
number = {15},
issn = {0095-9065},
address = {Washington, DC},
publisher = {ACS},
reportid = {DKFZ-2025-01446},
pages = {15711-15737},
year = {2025},
note = {2025 Aug 14;68(15):15711-15737},
abstract = {Limited aqueous solubility, high total polar surface area
(TPSA), and high hydrogen-bond donor (HBD) counts have
hampered the clinical development of VHL-based
proteolysis-targeting chimeras (PROTACs). This study
explores strategies to enhance the physicochemical
properties of VHL-recruiting USP7 degraders. By adjusting
lipophilicity, HBD count, and TPSA, we created degraders
with improved solubility while maintaining their USP7
degradation capability. Structural modifications at the VHL
ligand included a constrained six-membered ring in the
peptidic scaffold and the addition of solubilizing groups.
These changes enhanced aqueous solubility without
compromising degradation performance. A key example is
PROTAC 40, modified with a dibasic piperazine, which
exhibits a 170-fold increase in solubility over its
predecessor while retaining strong target selectivity. The
findings demonstrate that rational scaffold design can yield
solubility-enhanced VHL-based PROTACs with broad potential
for drug development. This methodology may also be
applicable to other E3 ligases, supporting the development
of degraders suitable for in vivo use.},
cin = {BE01},
ddc = {610},
cid = {I:(DE-He78)BE01-20160331},
pnm = {899 - ohne Topic (POF4-899)},
pid = {G:(DE-HGF)POF4-899},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:40673806},
doi = {10.1021/acs.jmedchem.5c00718},
url = {https://inrepo02.dkfz.de/record/302999},
}