Reactivity in cell culture medium and in vitro anticancer activity of 3,5-di-tert-butylcatechol: link to metal-catechol interactions
Frontiers in Chemical Biology,
Год журнала:
2025,
Номер
4
Опубликована: Фев. 3, 2025
Introduction
Catechol
moieties
are
common
in
natural
bioactive
molecules,
and
their
ability
to
bind
metal
ions
is
widely
explored
both
naturally
with
siderophores
the
development
of
metal-based
drugs.
The
reactivities
biology
activities
a
sterically
hindered
model
catechol
compound,
3,5-di-
tert
-butylcatechol
(dtbH
2
)
its
oxidation
product
-butyl-
o
-quinone
(dtbQ),
were
studied
cell
culture
medium
understand
better
medicinal
roles
this
class
molecules.
Methods
Anti-proliferative
dtbH
dtbQ
fresh
aged
solutions
molecules
two
human
cancer
lines,
T98G
(glioblastoma)
A549
(lung
carcinoma).
Electrospray
mass
spectrometry
UV/Vis
spectroscopy
used
study
buffer
medium,
presence
absence
glutathione
imidazole.
Results
Discussion
showed
high
anti-proliferative
activity
(IC
50
<
10
μM
72
h
assays)
lines
added
ions.
was
observed
when
freshly
while
pre-incubation
for
24
reduced
5-10-fold.
This
deactivation
avoided
biological
reductant,
(GSH),
at
physiologically
relevant
intracellular
concentration
(5.0
mM).
These
results
explained
by
speciation
studies
(UV/Vis
spectrometry)
aqueous
buffers,
or
organic
solvents
GSH.
that
redox
equilibrium
established
between
dtbQ,
latter
rapidly
coupling
GSH
an
oxidative
manner.
resultant
adduct
likely
be
responsible
toxicity
GSH-rich
cells
via
oxygen-dependent
radical
chain
reactions.
Deactivation
due
reactions
nucleophiles,
such
as
amino
acids,
followed
formation
polymeric
species.
reported
V(V)-catecholato
complexes
can
combination
efficient
cellular
uptake
rapid
decomposition
thiol-rich
environment
active
V(V)
/dtbQ
adducts
thiols
(mainly
GSH).
Slower
thiol-poor
extracellular
environments.
data
show
crucial
not
only
but
also
ligands
dissociates.
Язык: Английский
Synthesis, crystal structure, computational and solution studies of a new phosphotetradecavanadate salt. Assessment of its effect on U87 glioblastoma cells
Journal of Inorganic Biochemistry,
Год журнала:
2025,
Номер
269, С. 112882 - 112882
Опубликована: Март 9, 2025
Язык: Английский