ACS Chemical Biology,
Journal Year:
2024,
Volume and Issue:
19(2), P. 451 - 461
Published: Feb. 6, 2024
Enabling
control
over
the
bioactivity
of
proteins
with
light,
along
principles
photopharmacology,
has
potential
to
generate
safe
and
targeted
medical
treatments.
Installing
light
sensitivity
in
a
protein
can
be
achieved
through
its
covalent
modification
molecular
photoswitch.
The
general
challenge
this
approach
is
need
for
use
low
energy
visible
regulation
bioactivity.
In
study,
we
report
cytolytic
activity
protein.
A
water-soluble
visible-light-operated
tetra-ortho-fluoro-azobenzene
photoswitch
was
synthesized
by
utilizing
nucleophilic
aromatic
substitution
reaction
installing
solubilizing
sulfonate
group
onto
electron-poor
structure.
azobenzene
attached
two
cysteine
mutants
pore-forming
fragaceatoxin
C
(FraC),
their
respective
activities
were
evaluated
on
red
blood
cells.
For
both
mutants,
green-light-irradiated
sample,
containing
predominantly
cis-azobenzene
isomer,
more
active
compared
blue-light-irradiated
sample.
Ultimately,
same
modulation
pattern
observed
toward
hypopharyngeal
squamous
cell
carcinoma.
These
results
constitute
first
case
using
biological
toxic
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(30)
Published: April 7, 2023
Photopharmacology
is
an
attractive
approach
for
achieving
targeted
drug
action
with
the
use
of
light.
In
photopharmacology,
molecular
photoswitches
are
introduced
into
structure
biologically
active
small
molecules
to
allow
optical
control
their
potency.
Going
beyond
trial
and
error,
photopharmacology
has
progressively
applied
rational
design
methodologies
devise
light-controlled
bioactive
ligands.
this
review,
we
categorize
photopharmacological
efforts
from
standpoint
medicinal
chemistry
strategies,
focusing
on
diffusible
photochromic
ligands
modified
that
operate
through
E-Z
bond
isomerization.
vast
majority
cases,
photoswitchable
designed
as
analogs
existing
compounds,
a
variety
approaches.
By
analyzing
in
detail
comprehensive
list
instructive
examples,
describe
state
art
discuss
future
opportunities
photopharmacology.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(3), P. 1894 - 1903
Published: Jan. 11, 2024
Molecular
photoswitches
are
highly
desirable
in
all
chemistry-related
areas
of
research.
They
provide
effective
outside
control
over
geometric
and
electronic
changes
at
the
nanoscale
using
an
easy
to
apply,
waste-free
stimulus.
However,
simple
access
such
molecular
tools
is
typically
not
granted,
elaborate
syntheses
substitution
schemes
needed
order
obtain
efficient
photoswitching
properties.
Here
we
present
a
series
rhodanine-based
that
can
be
prepared
one
synthetic
step
without
requiring
purification.
Photoswitching
induced
by
UV
visible
light
both
switching
directions,
thermal
stabilities
metastable
states
as
well
quantum
yields
very
high.
An
additional
benefit
hydrogen-bonding
capacity
rhodanine
fragment,
which
enables
applications
supramolecular
or
medicinal
chemistry.
We
further
show
known
inhibitor
SMI-16a
photoswitchable
apoptosis
inducer.
The
biological
activity
effectively
switched
ON
OFF
reversible
photoisomerization
between
inactive
E
active
Z
isomer.
Rhodanine-based
therefore
represent
valuable
toolbox
for
implementing
responsiveness
breadth
functional
systems.
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
28(18)
Published: Dec. 29, 2021
Inspired
by
human
vision,
a
diverse
range
of
light-driven
molecular
switches
and
motors
have
been
developed
for
fundamental
understanding
application
in
material
science
biology.
Recently,
the
design
synthesis
visible
actively
pursued.
This
emerging
trend
is
partly
motivated
to
avoid
harmful
effects
ultraviolet
light,
which
was
necessary
drive
classical
at
least
one
direction,
impeding
their
employment
biomedical
photopharmacology
applications.
Moreover,
are
demonstrated
enable
benign
optical
materials
advanced
photonic
devices.
Therefore,
during
past
several
years,
based
on
azobenzene
derivatives,
diarylethenes,
1,2-dicyanodithienylethenes,
hemithioindigo
iminothioindoxyls,
donor-acceptor
Stenhouse
adducts,
overcrowded
alkene
judiciously
designed,
synthesized,
used
development
functional
systems
wide
In
this
Review,
we
present
recent
developments
toward
motors,
with
applications
fabrication
science,
bioscience,
pharmacology,
etc.
The
realized
so
far
undoubtedly
widen
scope
these
interesting
compounds
technological
biological
We
hope
Review
article
could
provide
additional
impetus
inspire
further
research
interests
future
exploration
materials,
systems,
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(12), P. 5614 - 5628
Published: March 15, 2022
Photoswitchable
reagents
are
powerful
tools
for
high-precision
studies
in
cell
biology.
When
these
globally
administered
yet
locally
photoactivated
two-dimensional
(2D)
cultures,
they
can
exert
micron-
and
millisecond-scale
biological
control.
This
gives
them
great
potential
use
biologically
more
relevant
three-dimensional
(3D)
models
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(6), P. 660 - 669
Published: Jan. 1, 2023
Fluorescence
microscopy
has
revolutionised
our
understanding
of
biological
systems,
enabling
the
visualisation
biomolecular
structures
and
dynamics
in
complex
systems.
The
possibility
to
reversibly
control
optical
or
biochemical
properties
fluorophores
can
unlock
advanced
applications
ranging
from
super-resolution
design
multi-stimuli
responsive
functional
biosensors.
In
this
Highlight,
we
review
recent
progress
small-molecule
photoswitches
applied
imaging
with
an
emphasis
on
molecular
engineering
strategies
promising
applications,
while
underlining
main
challenges
their
implementation.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(44), P. 23695 - 23704
Published: Aug. 30, 2021
We
report
the
first
cellular
application
of
emerging
near-quantitative
photoswitch
pyrrole
hemithioindigo,
by
rationally
designing
photopharmaceutical
PHTub
inhibitors
cytoskeletal
protein
tubulin.
PHTubs
allow
simultaneous
visible-light
imaging
and
photoswitching
in
live
cells,
delivering
cell-precise
photomodulation
microtubule
dynamics,
photocontrol
over
cell
cycle
progression
death.
This
is
acute
use
a
hemithioindigo
for
high-spatiotemporal-resolution
biological
control
cells.
It
additionally
demonstrates
utility
photoswitches,
enabling
dark-active
design
to
overcome
residual
background
activity
during
photopatterning.
work
opens
up
new
horizons
high-precision
research
using
shows
applicability
as
valuable
scaffold
range
other
targets.
Journal of Medicinal Chemistry,
Journal Year:
2022,
Volume and Issue:
65(19), P. 12594 - 12625
Published: Sept. 20, 2022
Hemiindigoids
comprise
a
range
of
natural
and
synthetic
scaffolds
that
share
the
same
aromatic
hydrocarbon
backbone
as
well
promising
biological
optical
properties.
The
encouraging
therapeutic
potential
these
has
been
unraveled
by
many
studies
over
past
years
uncovered
representants
with
inspiring
pharmacophoric
features
such
acetylcholinesterase
inhibitor
donezepil
tubulin
polymerization
indanocine.
In
this
review,
we
summarize
last
advances
in
medicinal
hemiindigoids,
special
attention
to
molecular
design,
structure–activity
relationship,
ligand-target
interactions,
mechanistic
explanations
covering
their
effects.
As
strong
fluorogenic
photoswitch
behavior
recently
started
be
highlighted
explored
biology,
giving
rise
development
novel
fluorescent
probes
photopharmacological
agents,
also
discuss
properties
chemistry
perspective.
Nature Communications,
Journal Year:
2022,
Volume and Issue:
13(1)
Published: Oct. 14, 2022
Abstract
Molecular
photoswitches
transform
light
energy
into
reversible
structural
changes.
Their
combination
with
known
pharmacophores
often
allows
for
photomodulation
of
the
biological
activity.
The
effort
to
apply
such
compounds
in
photopharmacology
as
light-activated
pro-drugs
is,
however,
hampered
by
serious
activity
reduction
upon
pharmacophore
modifications,
or
limited
biostability.
Here
we
report
that
a
potent
antimitotic
agent
plinabulin
and
its
derivatives
demonstrate
up
56-fold
photomodulation.
Alternatively,
irreversible
photoactivation
cyan
can
enhance
cytotoxicity
three
orders
magnitude—all
without
compromising
original
level,
structure
is
unchanged.
This
occurs
due
presence
peptide-derived
photoswitchable
motif
hemipiperazine
inside
scaffold.
Furthermore,
systematically
describe
photochromism
these
thermally
stable
biocompatible
hemipiperazines,
well
fluorophore
derived
from
plinabulin.
latter
may
further
expand
applicability
towards
super-resolution
microscopy.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(43)
Published: Aug. 30, 2022
A
survey
of
heterocyclic
hemithioindigo
photoswitches
is
presented
identifying
a
number
structural
motives
with
outstanding
property
profiles.
The
highly
sought-after
combination
pronounced
color
change,
quantitative
switching
in
both
directions,
exceptional
high
quantum
yields,
and
tunable
thermal
stability
metastable
states
can
be
realized
4-imidazole,
2-pyrrole,
3-indole-based
derivatives.
In
the
former,
an
unusual
preorganization
using
isomer
selective
chalcogen-
hydrogen
bonding
allows
to
precisely
control
geometry
changes
tautomerism
upon
switching.
Heterocyclic
hemithioindigos
thus
represent
promising
advanced
capabilities
that
will
great
value
anyone
interested
establishing
defined
reversible
at
molecular
level.
