723-62-6Relevant articles and documents
Fluorometric analysis of chlorite via oxidation of 9-anthracenecarboxaldehyde
Lee, Kang Min,Choi, Myung Gil,Yoo, Jae Hoon,Ahn, Sangdoo,Chang, Suk-Kyu
, (2021)
We investigated a simple fluorescence signaling method for the convenient analysis of a practical oxidant—chlorite—via the oxidation of 9-anthracenecarboxaldehyde to the corresponding carboxylic acid. 9-Anthracenecarboxaldehyde exhibited a marked ratiometric fluorescence signaling toward chlorite through manipulating its aggregation-induced emission property. The probe showed high chlorite-selectivity over other oxychlorine species as well as common metal ions, anions, and oxidants. Interference from a closely related oxidant, hypochlorite, was efficiently removed using DMSO as a scavenger. The proposed probe also exhibited a prominent ratiometric response through changes in UV–vis absorption behavior. Among the tested aromatic aldehydes (naphthaldehydes, anthracenecarboxaldehyde, and pyrenecarboxaldehyde), anthracene-based carboxaldehyde exhibited the most pronounced signaling contrast and the fastest signaling speed. The detection limit of chlorite determination was found to be 1.1 × 10–7 M. Exploitation of the probe for the convenient analysis of chlorite in tap water via a recovery test was conducted.
4-Biphenylaldehyde and 9-anthraldehyde: Two fluorescent substrates for determining P450 enzyme activities in rat and human
Marini,Grasso,Longo,Puccini,Riccardi,Gervasi, P. Giovanni
, p. 1 - 11 (2003)
1. 4-Biphenylaldehyde (4-BA) and 9-anthraldehyde (9-AA) were examined as substrates for cytochrome P450 (CYPs) enzymes in rat and human. Both aldehydes were oxidized by CYPs to fluorescent carboxylic acids, which can be assayed with a high sensitivity by an easy fluorimetric method. 2. With liver microsomes from control and induced rats, the oxidation of both 9-AA and 4-BA followed simple Michaelis-Menten kinetics. Only microsomes from rats pretreated with phenobarbital (a strong inducer of P4502B1/2) could increase (about threefold) the oxidation rates (Vmax) of both aldehydes above the control values, which were 6.7 ± 1.1 and 3.3 ± 0.6 nmolmin-1 mg-1 protein for 4-BA and 9-AA, respectively. On the other hand, the Km's, which were similar for both aldehydes (about 25 μM), did not change significantly with any inducer. The use of purified rat CYP1A1, 2E1, 2B1 and 2C11 in a reconstituted system showed that only 2B1 and 2C11 could oxidize both substrates with a high turnover. 3. In human liver microsomes, the oxidation rates of these aldehydes (1.6 ± 0.2 and 0.42 ± 0.1 nmolmin-1 mg-1 protein for 4-BA and 9-AA, respectively) were lower than those of rat but with similar Km's (20-26 μM). 4. The oxidation of these aldehydes was also determined with cDNA-expressed CYP1A1, 1A2, 2A6, 2B6, 2C9, 2D6, 2E1 and 3A4 and with a characterized bank of 14 human liver microsomes. In a reconstituted system, only CYP2B6, 2A6, 3A4 and with a lower turnover 2C9 oxidized both substrates. 5. Among the CYP marker activities of the 14 human samples, good correlations were only observed between CYP3A-dependent 6β-testosterone hydroxylase and the oxidation of 4-BA (r = 0.74) or 9-AA (r = 0.80) and between the oxidation of 4-BA versus 9-AA (r = 0.74). Weak correlations were also found between the 2B6-linked S-mephenytoin Ndemethylase and the oxidation of 4-BA (r = 0.58) or 9-AA (r = 0.65). 6. Inhibition experiments revealed that the oxidation of these aldehydes was inhibited by ketoconazole, 8-methoxypsoralene and sulphophenazole, selective inhibitors for P4503A6, 2A6 and 2C9, respectively. 7. In summary, based on the use of cDNA-expressed CYPs, correlation analysis and chemical inhibition, the metabolism in human liver microsomes of these aldehydes appears primarily catalysed by CYP3A, although CYP2A6, 2B6 and 2C9 may play a role. 9-AA and particularly 4-BA, owing to the high rate of its metabolism, may be two novel useful fluorescent probe substrates for assaying CYP activities in various species.
Surface active ionic liquid assisted metal-free electrocatalytic-carboxylation in aqueous phase: A sustainable approach for CO2utilization paired with electro-detoxification of halocarbons
Bhat, Khursheed Ahmad,Bhat, Mohsin Ahmad,Bhat, Sajad Ahmad,Ingole, Pravin P.,Manzoor Bhat, Zahid,Pandit, Sarwar Ahmad,Rather, Mudasir Ahmad,Rehman, Shakeel U.,Sofi, Feroz Ahmad,Thotiyl, Musthafa Ottakam
, p. 9992 - 10005 (2021/12/24)
Electrocarboxylation of halocarbons is a promising green synthetic strategy for capture, fixation and utilization of CO2 for the synthesis of high-added-value industrial compounds. However, the unparalleled kinetic/thermodynamic stability and solubility concerns of CO2 and halocarbons warrant the use of appropriate (often precious metal based) electrocatalytic electrodes and environmentally non-green solvent systems to drive this otherwise kinetically slow electrochemical process. Herein we demonstrate that owing to their unique solubility and excellent electrocatalytic properties, the aqueous micellar solutions of imidazolium-based surface active ionic liquids (SAILs) can be used for the efficient and selective electrocatalytic-carboxylation of halocarbons to produce carboxylic acids. Specifically, we present results from our detailed electrochemical investigations regarding the electroreductive cleavage of the C-X bond and electrocarboxylation of 9-bromoanthracene (9-BAN) and chloroacetonitrile (CAN) in buffered (pH 7, phosphate buffer) micellar solutions of 1-dodecyl-3-methyl-imidazolium chloride ([DDMIM][Cl]). We demonstrate that the unique ability of [DDMIM][Cl] micelles to stabilize the electrogenerated reactive intermediates facilitates a novel reaction pathway that ensures selective and efficient electrocatalytic-reductive carboxylation of 9-BAN and CAN. The presented results clearly establish that besides allowing for the electrocarboxylation of halocarbons in aqueous green electrolytes, the use of SAILs ensures electrochemical fixation of CO2 at practically low cost current and potential conditions imposed over metal free, economically viable and electrochemically robust carbon electrodes. The use of SAILs is reported to improve the faradaic efficiency (～95%) and reduce the chances of undesired side product reactions which continue to be a major concern in the state of art electro-carboxylation processes. The presented approach we opine offers a promising avenue toward design of eco-green pathways in the direction of CO2 fixation and electro-organic synthesis of a diverse range of value-added products from water insoluble halocarbons (toxic pollutants) in aqueous media.
Method for copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide
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Paragraph 0095; 0096, (2019/12/29)
The invention discloses a method for a copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide. According to the method, carbon dioxide is used as a C1 source, copper catalysisis adopted, alkoxide serves as alkali, and a reaction is carried out in an organic solvent; the method is simple in process and easy to implement, and shows wide functional group compatibility; the method allows various arylboronic acids such as monosubstituted or polysubstituted phenylboronic acid, polycyclic aromatic hydrocarbon boronic acid and benzoheterocyclic boronic acid to be converted into corresponding arylcarboxylic acids with considerable yield under mild conditions; and the produced carboxylic acids have important application value, and can be used for deriving a great number of other common chemical substances, such as acyl halide, acid anhydride, ester and amide.
