A novel amphiphilic aggregation-induced emission (AIE) copolymer, that is, poly(NIPAM-co-TPE-SP), consisting of N-isopropylacrylamide (NIPAM) as a hydrophilic unit and a tetraphenylethylene-spiropyran monomer (TPE-SP) as a bifluorophoric unit is reported. Upon UV exposure, the close form of non-emissive spiropyran (SP) in poly(NIPAM-co-TPE-SP) can be photo-switched to the open form of emissive merocyanine (MC) in poly(NIPAM-co-TPE-MC) in an aqueous solution, leading to ratiometric fluorescence of AIEgens between green TPE and red MC emissions at 517 and 627 nm, respectively, via Förster resonance energy transfer (FRET). Distinct FRET processes of poly(NIPAM-co-TPE-MC) can be observed under various UV and visible light irradiations, acid-base conditions, thermal treatments, and cyanide ion interactions, which are also confirmed by theoretical studies. The subtle perturbations of environmental factors, such as UV exposure, pH value, temperature, and cyanide ion, can be detected in aqueous media by distinct ratiometric fluorescence changes of the FRET behavior in the amphiphilic poly(NIPAM-co-TPE-MC). Moreover, the first FRET sensor polymer poly(NIPAM-co-TPE-MC) based on dual AIEgens of TPE and MC units is developed to show a very high selectivity and sensitivity with a low detection limit (LOD = 0.26 μM) toward the cyanide ion in water, which only contain an approximately 1% molar ratio of the bifluorophoric content and can be utilized in cellular bioimaging applications for cyanide detections.
Several 2-substituted and 2,5-disubstituted piperazine-3,6-diones were synthesized starting from readily available alpha-amino acids. After activation of a lactam carbonyl via introduction of a methoxycarbonyl group onto nitrogen, this carbonyl was selectively reduced. Treatment of the resulting urethane with protic acid generated the corresponding N-acyliminium ion, which was trapped by a nucleophilic C2-side chain to provide 2,6-bridged piperazine-3-ones. Several aromatic, heteroaromatic, and nonaromatic side chains were used as pi-nucleophiles. In addition, the effect of the presence of a C5-methyl group on the stereochemical outcome of the cyclization was examined.
A series
of novel photo-switchable [2]rotaxanes (i.e., Rot-A-SP and Rot-B-SP before and after shuttling controlled
by acid–base, respectively) containing one spiropyran (SP)
unit (as a photochromic stopper) on the axle and two tetraphenylethylene
(TPE) units on the macrocycle were synthesized via click reaction.
Upon UV/visible light exposure, both mono-fluorophoric rotaxanes Rot-A-SP and Rot-B-SP with the closed form (i.e.,
non-emissive SP unit) could be transformed into the open form (i.e.,
red-emissive merocyanine (MC) unit) to acquire their respective bi-fluorophoric Rot-A-MC and Rot-B-MC reversibly. The aggregation-induced
emission (AIE) properties of bi-fluorophoric TPE combined with MC
AIEgens of these designed rotaxanes and mixtures in semi-aqueous solutions
induced interesting ratiometric photoluminescence (PL) and Förster
resonance energy transfer (FRET) behaviors, which were further investigated
and verified by dynamic light scattering (DLS), X-ray diffraction
(XRD), and time-resolved photoluminescence (TRPL) measurements along
with theoretical studies. Accordingly, in contrast to the model axle
(Axle-MC) and the analogous mixture (Mixture-MC, containing the axle and macrocycle components in a 1:1 molar ratio),
more efficient FRET behaviors and stronger red PL emissions were obtained
from dual-AIEgens between a blue-emissive TPE donor (PL emission at
468 nm) and a red-emissive MC acceptor (PL emission at 668 nm) in
both novel photo-switchable [2]rotaxanes Rot-A-MC and Rot-B-MC under various external modulations, including water
content, UV/Vis irradiation, pH value, and temperature. Furthermore,
the reversible fluorescent photo-patterning applications of Rot-A-SP in a powder form and a solid film with excellent
photochromic and fluorescent behaviors are first investigated in this
report.
We have synthesized 50 benzimidazole (BMZ) derivatives with 1,2‐phenylenediamines and aromatic aldehydes under mild oxidation conditions by using inexpensive, nontoxic inorganic salt sodium metabisulfite in a one‐pot condensation reaction and screened their ability to interfere with Zika virus (ZIKV) infection utilizing a cell‐based phenotypic assay. Seven BMZs inhibited an African ZIKV strain with a selectivity index (SI=CC50/EC50) of 9–37. Structure‐activity relationship analysis demonstrated that substitution at the C‐2, N‐1, and C‐5 positions of the BMZ ring were important for anti‐ZIKV activity. The hybrid structure of BMZ and naphthalene rings was a structural feature responsible for the high anti‐ZIKV activity. Importantly, BMZs inhibited ZIKV in human neural stem cells, a physiologically relevant system considering the severe congenital anomalies, like microcephaly, caused by ZIKV infection. Compound 39 displayed the highest antiviral efficacy against the African ZIKV strain in Huh‐7 (SI>37) and neural stem cells (SI=12). Compound 35 possessed the highest activity in Vero cells (SI=115). Together, our data indicate that BMZs derivatives have to be considered for the development of ZIKV therapeutic interventions.
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