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@ARTICLE{Bochicchio:280465,
author = {Bochicchio, Anna and Rossetti, Giulia and Tabarrini, Oriana
and Krauβ, Sybille and Carloni, Paolo},
title = {{M}olecular {V}iew of {L}igands {S}pecificity for {CAG}
{R}epeats in {A}nti-{H}untington {T}herapy},
journal = {Journal of chemical theory and computation},
volume = {11},
number = {10},
issn = {1549-9626},
address = {Washington, DC},
publisher = {American Chemical Society (ACS)},
reportid = {FZJ-2016-00239},
pages = {4911 - 4922},
year = {2015},
abstract = {Huntington’s disease is a fatal and devastating
neurodegenerative genetic disorder for which there is
currently no cure. It is characterized by Huntingtin
protein’s mRNA transcripts with 36 or more CAG repeats.
Inhibiting the formation of pathological complexes between
these expanded transcripts and target proteins may be a
valuable strategy against the disease. Yet, the rational
design of molecules specifically targeting the expanded CAG
repeats is limited by the lack of structural information.
Here, we use well-tempered metadynamics-based free energy
calculations to investigate pose and affinity of two ligands
targeting CAG repeats for which affinities have been
previously measured. The first consists of two
4-guanidinophenyl rings linked by an ester group. It is the
most potent ligand identified so far, with Kd = 60(30) nM.
The second consists of a 4-phenyl dihydroimidazole and
4–1H-indole dihydroimidazole connected by a C–C bond (Kd
= 700(80) nM). Our calculations reproduce the experimental
affinities and uncover the recognition pattern between
ligands’ and their RNA target. They also provide a
molecular basis for the markedly different affinity of the
two ligands for CAG repeats as observed experimentally.
These findings may pave the way for a structure-based
hit-to-lead optimization to further improve ligand
selectivity toward CAG repeat-containing mRNAs.},
cin = {JSC / IAS-5 / INM-9 / GRS Jülich ; German Research School
for Simulation Sciences},
ddc = {540},
cid = {I:(DE-Juel1)JSC-20090406 / I:(DE-Juel1)IAS-5-20120330 /
I:(DE-Juel1)INM-9-20140121 / I:(DE-Juel1)GRS-20100316},
pnm = {511 - Computational Science and Mathematical Methods
(POF3-511) / 572 - (Dys-)function and Plasticity (POF3-572)},
pid = {G:(DE-HGF)POF3-511 / G:(DE-HGF)POF3-572},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000362921700040},
pubmed = {pmid:26574279},
doi = {10.1021/acs.jctc.5b00208},
url = {https://juser.fz-juelich.de/record/280465},
}