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1.
Org Biomol Chem ; 21(40): 8201, 2023 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-37814908

RESUMO

Correction for 'Turn-on fluorogenic sensors based on an anthraquinone signaling unit for the detection of Zn(II) and Cd(II) ions' by Chawanakorn Kongsak et al., Org. Biomol. Chem., 2023, 21, 7367-7381, https://doi.org/10.1039/D3OB01223A.

2.
Org Biomol Chem ; 21(36): 7367-7381, 2023 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-37655509

RESUMO

Turn-on fluorescent chemosensors based on an anthraquinone moiety, N,N'-(9,10-dioxo-9,10-dihydroanthracene-1,8-diyl)bis(2-(bis(pyridin-2-ylmethyl)amino)acetamide) (1) and N,N'-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-(bis(pyridin-2-ylmethyl)amino)acetamide) (2), have been successfully synthesized with the overall yields of 61% and 90%, respectively. The structures of both chemosensors 1 and 2 were elucidated using several spectroscopic techniques such as 1H NMR, 13C NMR, 2D-NMR, FTIR and HRMS. The target chemosensor 1 is a promising tool for the detection of trace levels of d10 metal ions, such as Zn(II) and Cd(II) ions, by exhibiting a significant fluorescence enhancement via a turn-on photoinduced electron transfer (PET) mechanism with a rapid and highly reproducible signal, and low detection limit values of 0.408 µM and 0.246 µM, for Zn(II) and Cd(II), respectively.

3.
Int J Biol Macromol ; 253(Pt 3): 126809, 2023 Dec 31.
Artigo em Inglês | MEDLINE | ID: mdl-37709235

RESUMO

This study focuses on the synergistic formulation of environmentally friendly blended materials based on carboxymethyl cellulose (CMC) for advanced interactive wound dressing. New CMC hydrogels were prepared with two degrees of functionalization and chemically crosslinked with citric acid (CA) to fine-tune their properties. Additionally, CMC-based hybrids were created by blending with shellac (SHL) and incorporating self-antibacterial hydroxyapatite (HA) to inhibit bacterial growth and promote wound healing. The results demonstrate the successful production of superabsorbent hydrogels with typical swelling degrees ranging from 81% in water to 82% in phosphate-buffered saline (PBS). These hydrogels exhibit distinct morphological features and remarkable improvements in surface mechanical properties, specifically in their tensile properties, which show a significant increase from approximately 0.03 to 2.2 N/mm2 due to the formation of CMC-SHL-HA hybrid nanostructures. Furthermore, the cytocompatibility of these CMC-based hydrogels was investigated by assessing the in vitro cell viability responses of human skin fibroblasts. The results reveal the cell viability responses over 91%, indicating their biocompatibility with human cells. Moreover, the characteristics of surgical wounds were assessed before and after the application of the hydrogel on dogs, and no signs of infection were observed at any of the surgical sites post-surgery.


Assuntos
Carboximetilcelulose Sódica , Durapatita , Humanos , Animais , Cães , Durapatita/farmacologia , Carboximetilcelulose Sódica/farmacologia , Carboximetilcelulose Sódica/química , Antibacterianos/farmacologia , Hidrogéis/farmacologia , Hidrogéis/química , Bandagens
4.
J Org Chem ; 87(18): 12052-12064, 2022 Sep 16.
Artigo em Inglês | MEDLINE | ID: mdl-36073019

RESUMO

The Lewis acid organocatalytic system of lithium tetramethylene-tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene (1,4-bisNHC) including lithium benzyloxide and benzyl alcohol has been successfully utilized in the ring-opening polymerization (ROP) of ε-caprolactone (CL) for the first time. The catalytic performance of this organic catalyst in the synthesis of high-molecular-weight polymers was investigated via bulk polymerization using different combinations of tetramethylene-tethered bis[N-(N'-butylimidazolium)] hexafluorophosphate (1,4-bis[Bim][PF6]), benzyl alcohol (BnOH), and n-butyl lithium (nBuLi) ([1,4-bis[Bim][PF6]]/[BnOH]/[nBuLi]) with the molar ratios of 0:2:2, 1:1:3, 1:2:3, and 1:2:4. The results showed that the molar ratio of 1:2:3 efficiently and rapidly initiated the bulk ROP of CL at room temperature with a high molar ratio of CL to 1,4-bis[Bim][PF6] of 3000/1 and produced the highest number of average-molecular-weight (Mn) poly(ε-caprolactone) (103,057 g mol-1) with the dispersity (D̵) and %conversion of 1.73 and 98% in a short period of time (152 s). From comparative studies, the relative polymerization rates of the bulk ROP of CL with different [1,4-bis[Bim][PF6]]/[BnOH]/[nBuLi] molar ratios was determined in the following order: 1:2:4 > 1:1:3 > 1:2:3 > 0:2:2. For mechanistic investigation, the bulk ROP mechanism of CL with our organic catalyst was proposed through the intramolecular bis-lithium-carbene interaction pathway for 1,4-bisNHC1,1,3, 1,4-bisNHC1,2,3, and 1,4-bisNHC1,2,4 systems.

5.
Polymers (Basel) ; 13(24)2021 Dec 08.
Artigo em Inglês | MEDLINE | ID: mdl-34960841

RESUMO

In this work, we successfully synthesized high thermal stable 1,n-bis(N-(N'-butylimidazolium)alkane bishexafluorophosphates (1,n-bis[Bim][PF6], n = 4, 6, 8, and 10) catalysts in 55-70% yields from imidazole which were applied as non-toxic DILs catalysts with 1-butanol as initiator for the bulk ROP of ε-caprolactone (CL) in the varied ratio of CL/nBuOH/1,4-bis[Bim][PF6] from 200/1.0/0.25-4.0 to 700/1.0/0.25-4.0 by mol%. The result found that the optimal ratio of CL/nBuOH/1,4-bis[Bim][PF6] 400/1.0/0.5 mol% at 120 °C for 72 h led to the polymerization conversions higher than 95%, with the molecular weight (Mw) of PCL 20,130 g mol-1 (D~1.80). The polymerization rate of CL increased with the decreasing linker chain length of ionic liquids. Moreover, the mechanistic study was investigated by DFT using B3LYP (6-31G(d,p)) as basis set. The most plausible mechanism included the stepwise and coordination insertion in which the alkoxide insertion step is the rate-determining step.

6.
Org Biomol Chem ; 19(41): 9081, 2021 Oct 27.
Artigo em Inglês | MEDLINE | ID: mdl-34657953

RESUMO

Correction for 'Synthesis and application of methyl itaconate-anthracene adducts in configuration assignment of chiral secondary alcohols by 1H NMR' by Puracheth Rithchumpon et al., Org. Biomol. Chem., 2021, DOI: 10.1039/D1OB01387D.

7.
Org Biomol Chem ; 19(41): 8955-8967, 2021 10 27.
Artigo em Inglês | MEDLINE | ID: mdl-34581721

RESUMO

Novel chiral derivatising agents (CDAs) such as methyl itaconate-anthracene adducts (MIAs) were reported for the absolute configuration determination of chiral secondary alcohols by the 1H NMR technique. These adducts were facilely prepared through well-known reactions, and furthermore, commercially available starting materials. According to these synthetic routes, the desired MIAs were afforded in 6 steps with 49% overall yield from dimethyl itaconate. Moreover, the represented MIAs provided significantly large differences of chemical shift values (ΔδSR). No racemisation from the tertiary characteristics of the adjacent alpha carbon was observed.

8.
Org Biomol Chem ; 17(3): 541-554, 2019 01 16.
Artigo em Inglês | MEDLINE | ID: mdl-30574639

RESUMO

New alternative chiral derivatizing agents, ß-keto-anthracene adducts (KAAs), were accomplished and the influence of aromatic moieties at the α-carbon position for elucidation of the absolute configuration of chiral secondary alcohols via NMR was studied. The α-benzoyl substituted KAAs strongly enhance the anisotropic effect which produced greater ΔδRS values than other conventional reagents. We propose a simplified model to describe the conformations and to assign the absolute configuration in several chiral alcohol samples.

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