Dicyclohexylcarbodiimide Research Articles

Functional electrolyte: Design of corrosion inhibition additives to protect Cu current collectors in over-discharged state

Lithium-ion secondary batteries are increasingly being used not only for ICT devices but also for large power sources such as EVs. Typically, the battery module discharge termination voltage is fixed in the device/power supply, but the sequentially connected single cells in the assembled battery may become over-discharged, thus there is a concern that the battery performance is degraded by the dissolution of the Cu current collector. Cu ions diffuse into the electrolyte due to the dissolution of the Cu current collector and precipitate on the anode during charging. This causes blackening of the Cu surface and an increase in cell resistance, and if it progresses further, it may lead to a short circuit. Therefore, we searched for an additive that would improve the battery performance by suppressing the dissolution of Cu, which causes a short circuit during over-discharge. Since 1999, we have proposed a "functional electrolyte" in which a small amount of an additive with a new function is added to the electrolyte. In this work, we focused on additives with carbodiimide groups (-N=C=N-) that prevent dissolution of the Cu collectors during over-discharge and improve the battery performance, and report the finding that N,N′-dicyclohexylcarbodiimide (DCC) exhibits such a unique behavior.

Outbreak of contact allergy to dicyclohexylcarbodiimide in a biotechnology laboratory.

Dicyclohexylcarbodiimide (DCC) is known to cause occupational allergic contact dermatitis in biotechnology laboratory workers. This study aimed to assess the prevalence of DCC sensitization among workers of one biosynthesis laboratory and to determine the optimal DCC concentration for patch testing. 23 laboratory workers frequently exposed to DCC of whom 21 suffered from dermatitis and 11 controls were enrolled into the study. All participants underwent skin patch testing with different concentrations of DCC and other substances used in the work environment. Statistical analysis was conducted to compare results between active and control groups. Of the 23 workers tested, 56.5% showed positive reactions to DCC. All of them had dermatitis. Morpholine also elicited positive reactions in 26.1% of workers who were all sensitized to DCC. Dimethylformamide and chloroform yielded negative results. Dicyclohexylcarbodiimide was a major cause of contact dermatitis in the active group indicating an outbreak of contact allergy to DCC in the company necessitating preventive measures. Both DCC 0.1% ac. and DCC 0.05% pet. should both be used for patch testing.

Sodium transport and redox regulation in Saccharomyces cerevisiae under osmotic stress depending on oxygen availability

This study explores the molecular mechanisms behind the differential responses of Saccharomyces cerevisiae industrial strains (ATCC 9804 and ATCC 13007) to osmotic stress. We observed that, in contrast to ATCC 9804 strain, sodium flux in ATCC 13,007 is not N, N’-dicyclohexylcarbodiimide (DCCD)-sensitive under osmotic stress, suggesting a distinct ion homeostasis mechanism. Under aerobic conditions, osmotic stress increased reduced SH groups by 45% in ATCC 9804 and 34% in ATCC 13,007. In contrast, under microaerophilic conditions, both strains experienced a 50% reduction in thiol groups. Notably, ATCC 13,007 exhibited a 1.5-fold increase in catalase (CAT) activity under aerobic stress compared to standard conditions, while ATCC 9804 showed enhanced CAT activity due to SH group binding. Additionally, superoxide dismutase (SOD) activity was doubled during aerobic growth in both strains, with ATCC 13,007 showing a 1.5-fold higher SOD activity under osmotic stress. The results demonstrate that S. cerevisiae adapts to osmotic stress differently under aerobic and microaerophilic conditions, with aerobic conditions promoting Pma-Ena-Trk interplay, reduced thiol levels and increased catalase activity, while microaerophilic conditions demonstrate Pma-Nha-Trk interplay and shifts redox balance towards oxidized thiol groups and enhance superoxide dismutase activity. Understanding these mechanisms can aid in developing stress-resistant yeast strains for industrial applications.

Preparation of Glutathione-Responsive Paclitaxel Prodrug Based on Endogenous Molecule of L-Glutathione Oxidized for Cancer Therapy.

Using an endogenous carrier is the best method to address the biocompatibility of carriers in the drug delivery field. Herein, we prepared a glutathione-responsive paclitaxel prodrug micelle based on an endogenous molecule of L-glutathione oxidized (GSSG) for cancer therapy using one-pot synthesis. The carboxyl groups in L-glutathione oxidized were reacted with the hydroxyl group in paclitaxel (PTX) using the catalysts dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP). Then, the amino-polyethylene glycol monomethyl ether (mPEG-NH2) was conjugated with GSSG to prepare PTX-GSSG-PEG. The structure of PTX-GSSG-PEG was characterized using infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS). The drug release kinetics of PTX within PTX-GSSG-PEG were quantified using ultraviolet spectroscopy (UV-Vis). The size of the PTX-GSSG-PEG micelles was 83 nm, as evaluated using dynamic light scattering (DLS), and their particle size remained stable in a pH 7.4 PBS for 7 days. Moreover, the micelles could responsively degrade and release PTX in a reduced glutathione environment. The drug loading of PTX in PTX-GSSG-PEG was 13%, as determined using NMR. Furthermore, the cumulative drug release rate of PTX from the micelles reached 72.1% in a reduced glutathione environment of 5 mg/mL at 120 h. Cell viability experiments demonstrated that the PTX-GSSG-PEG micelles could induce the apoptosis of MCF-7 cells. Additionally, cell uptake showed that the micelles could distribute to the cell nuclei within 7 h. To sum up, with this glutathione-responsive paclitaxel prodrug micelle based on the endogenous molecule GSSG, it may be possible to develop novel nanomedicines in the future.

Synthesis of N-Alkyl-3-[2-oxoquinolin-1(2H)-yl]propanoic Acid Derivatives and Related Compounds: Cytotoxicity and EGFR Inhibition of Some Propanamide Derivatives.

A series of 20 new structure-modified quinolin-2-one derivatives were prepared for biological evaluation. This was successfully achieved based on chemoselective reactions of heterocyclic amides with acrylic acid derivatives, which gave 3-[2-oxoquinolin-1-(2H)-yl] propanoic acid derivatives (N-substitution via a unique behavior). The ester was reacted with hydrazine to afford the corresponding hydrazide. Both the corresponding ester and hydrazide were used as building blocks to modify the quinolone structure and give N-hydroxyl propanamides, oxadiazoles, and thiosemicarbazides. The corresponding carboxylic acid and hydrazide were used to prepare several amides: N-alkyl-3-[2-oxoquinolin-1(2H)-yl]propanamides via azide and dicyclohexyl carbodiimide coupling methods. Among derivatives, compound 9e exhibited potent cytotoxicity against MCF-7 cells with an IC50 value of 1.32 μM compared to doxorubicin with an IC50 value of 1.21 μM. Additionally, it caused potent EGFR inhibition by 97% with an IC50 value of 16.89 nM compared to Erlotinib with an IC50 value of 29.8 nM. Finally, the binding mode of compound interactions toward EGFR was highlighted using a molecular docking study; compound 9e exhibited good binding affinity with a binding energy of -17.89 kcal/mol, and it formed H-bond interactions with Met 769 as the key amino acid of interaction. Accordingly, compound 9e may be developed as an EGFR-oriented chemotherapeutic antibreast cancer agent.

Inhibition of the ATP synthase increases sensitivity of Escherichia coli carrying mcr-1 to polymyxin B.

Bacterial infections caused by multidrug-resistant (MDR) gram-negative strains carrying the mobile colistin resistance gene mcr-1 are serious threats to world public health due to the lack of effective treatments. Inhibition of the ATP synthase makes bacteria such as Staphylococcus aureus and Klebsiella pneumoniae more sensitive to polymyxin. This provides new strategies for treating infections caused by polymyxins-resistant bacteria carrying mcr-1. Six mcr-1-positive strains were isolated from clinical samples, and all were identified as Escherichia coli. Here we investigated several ATP synthase inhibitors, N,N'-dicyclohexylcarbodiimide (DCCD), resveratrol, and piceatannol, for their antibacterial effects against the mcr-1-positive strains combined with polymyxin B (POL). Checkerboard assay, time-kill assay, biofilm inhibition and eradication assay indicated the significant synergistic effect of ATP synthase inhibitors/POL combination in vitro. Meanwhile, mouse infection model experiment was also performed, showing a 5 log10 reduction of the pathogen after treatment with the resveratrol/POL combination. Moreover, adding adenosine disodium triphosphate (Na2ATP) could inhibit the antibacterial effect of the ATP synthase inhibitors/POL combination. In conclusion, our study confirmed that inhibition of ATP production could increase the susceptibility of bacteria carrying mcr-1 to polymyxins. This provides a new strategy against polymyxins-resistant bacteria infection.

Dicyclohexylcarbodiimide and disodium succinate regulate the pulp softening and breakdown in fresh longan by modulating the metabolism of cell wall polysaccharides

Cell wall polysaccharides (CWP) are an important component of cell structure, and its content variation is a primary factor affecting the texture of fresh longan. The influences of dicyclohexylcarbodiimide (DCC) and disodium succinate (DS) treatments on the pulp softening and pulp breakdown, and their relation to CWP metabolism in pulp of longan fruit were explored. Compared with the control longan, DCC-treated fruit showed lower value of pulp firmness, higher index of pulp breakdown, higher expression levels of cell wall disassembly enzymes (CWDEs)-related genes (DlPME1, DlPME3, DlPG1, Dlβ-Gal1, Dlβ-Gal16, DlCx7, DlXET3, DlXET27), and higher activities of CWDEs including pectin methyl esterase (PME), polygalacturonase (PG), β-galactosidase (β-Gal), cellulase (Cx), xyloglucan endotransglycosylase (XET), lower values of cell wall materials, and lower levels of CWP including ionic-soluble pectin, covalent-soluble pectin, cellulose, and hemicellulose. Whereas, the opposite effects were exhibited in DS-treated fruit. The above data indicate that DCC-hastened longan pulp softening and pulp breakdown was due to the up-regulating expressions of CWDEs-related genes, the activating activities of CWDEs, and the accelerating CWP disassembly by DCC treatment. Whereas, DS repressed longan pulp softening and pulp breakdown through down-regulating the expressions of CWDEs-related genes, inhibiting CWDEs activities, and reducing CWP degradation.

Developmentand validation of carbodiimide-activated ELISA plate for quantifying IgG levels against Streptococcus pneumoniae capsular polysaccharides.

Background:Conventional microtiter plates lack the surface strength needed for effective binding of pneumococcalpolysaccharide antigens. This study tackles the limitation by altering the surface of polystyrene plates through carbodiimide activation under acidic pH conditions.Method:The microtiter plates were activated with carbodiimide coupling agents, N,N'-Dicyclohexylcarbodiimide (DCC) and N-Hydroxysuccinimide (NHS). They were subsequently coated with 13 pneumococcal antigens at a concentration of 5 μg/ml with a pH of 3.5. The IgG antibody titer was assessed utilizing the World Health Organization (WHO) ELISA protocol for 30 human serum samples. In addition, validation experiments were conducted to evaluate specificity and precision.Results: The modified plates exhibited two-times higher antibody titers compared to conventional plates across all 13 serotypes. Observations revealed elevated antibody levels, with geometric concentrations ranging between 0.96 μg/ml and 4.24 μg/ml.Conclusion:Carbodiimide activation and acidic pH modification of microtiter plates enhance sensitivity and specificity in detecting pneumococcal antibodies, critical for vaccination planning and immunity assessment.

STUDY OF THE INHIBITORY EFFECTS OF VITAMIN E DERIVATIVES ON MITOCHONDRIAL COMPLEX II SUBUNIT USING MOLECULAR DOCKING

Objective: The goal of this study was to create vitamin E derivatives and explore their potential anticancer properties using a computational approach. Methods: The Steglich method was used for the synthesis of the vitamin E-fatty acid (pentanoic acid, heptanoic acid, and octanoic acid) derivatives, with N,N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as the catalysts. The structure of the synthesized products was determined by ultraviolet-visible (UV-Vis) spectroscopy, fourier transform infrared (FTIR) spectroscopy, and liquid chromatography-mass spectrometry (LC-MS). Molecular docking was carried out on the succinate dehydrogenase (SDH) enzyme using AutoDockTools. Results: α–Tocopherol pentanoate (α–TP), α–tocopherol heptanoate (α–TH), and α–tocopherol octanoate (α–TO) were the three vitamin E derivatives synthesized in this study. Based on the results of molecular docking, the novel compounds (α–TP, α–TH, and α–TO) generated bond energies of-10.57,-9.61, and-9.20 kcal/mol, respectively. Conclusion: All newly synthesized compounds exhibited lower binding affinity values than α–tocopherol (α–T). This confirms that these compounds might not provide greater advantages than α-tocopherol in terms of inhibitory effects on mitochondrial complex II (CII).

Proton conductance and regulation of proton/potassium fluxes in Escherichia coli FhlA-lacking cells during fermentation of mixed carbon sources

Escherichia coli uptake potassium ions with the coupling of proton efflux and energy utilization via proton FOF1-ATPase. In this study contribution of formate hydrogen lyase (FHL) complexes in the proton/potassium fluxes and the formation of proton conductance (CMH+) were investigated using fhlA mutant strain. The proton flux rate (JH+) decreased in fhlA by ∼ 25 % and ∼70 % during the utilization of glucose and glycerol, respectively, at 20 h suggesting H+ transport via or through FHL complexes. The decrease in JK+ in fhlA by ∼40 % proposed the interaction between FHL and Trk secondary transport system during mixed carbon fermentation. Moreover, the usage of N,N′-dicyclohexylcarbodiimide (DCCD) demonstrated the mediation of FOF1-ATPase in this interaction. CMH+ was 13.4 nmol min−1 mV−1 in WT at 20 h, which decreased by 20 % in fhlA. Taken together, FHL complexes have a significant contribution to the modulation of H+/K+ fluxes and the CMH + for efficient energy transduction and regulation of the proton motive force during mixed carbon sources fermentation.

Synthesis and Characterization of New Nanohybrids Based on Carboxymethyl Scleroglucan and Silica Nanoparticles.

In this study, two new nanohybrids (NH-A and NH-B) were synthesized through carbodiimide-assisted coupling. The reaction was performed between carboxymethyl-scleroglucans (CMS-A and CMS-B) with different degrees of substitution and commercial amino-functionalized silica nanoparticles using 4-(dimethylamino)-pyridine (DMAP) and N,N'-dicyclohexylcarbodiimide (DCC) as catalysts. The morphology and properties of the nanohybrids were investigated by using transmission (TEM) and scanning electron microscopy (SEM), electron-dispersive scanning (EDS), attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FT-IR), X-ray photoelectron spectroscopy (XPS), powder X-ray diffraction (XRD), inductively coupled plasma atomic emission spectroscopy (ICP-OES), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic light scattering (DLS). The nanohybrids exhibited differences in structure due to the incorporation of polyhedral oligomeric silsesquioxane (POSS) materials. The results reveal that hybrid nanomaterials exhibit similar thermal properties but differ in morphology, chemical structure, and crystallinity properties. Finally, a viscosity study was performed on the newly obtained nanohybrid materials; viscosities of nanohybrids increased significantly in comparison to the carboxymethyl-scleroglucans, with a viscosity difference of 7.2% for NH-A and up to 32.6% for NH-B.

Synthesis of BODIPY FL-tethered ridaifen-B, RID-B-BODIPY, and its localization in cancer cells.

We synthesized ridaifen-B boron dipyrromethene (RID-B-BODIPY) using 2-methyl-6-nitro benzoic anhydride (MNBA)-mediated dehydration condensation reaction between amino alkyl-tethered RID and BODIPY FL. Comparative experiments between dicyclohexylcarbodiimide (DCC) and MNBA for their coupling reactions demonstrated that MNBA is an effective condensation reagent for amines and BODIPY FL. A cell staining study with RID-B-BODIPY showed intracellular localization of BODIPY FL fluorescence, attributed to the RID-B structure, indicating the successful development of a tool for analyzing intracellular molecular behavior efficiently.

Evidence for bidirectional formic acid translocation in vivo via the Escherichia coli formate channel FocA

Pentameric FocA permeates either formate or formic acid bidirectionally across the cytoplasmic membrane of anaerobically growing Escherichia coli. Each protomer of FocA has its own hydrophobic pore, but it is unclear whether formate or neutral formic acid is translocated in vivo. Here, we measured total and dicyclohexylcarbodiimide (DCCD)-inhibited proton flux out of resting, fermentatively grown, stationary-phase E. coli cells in dependence on FocA. Using a wild-type strain synthesizing native FocA, it was shown that using glucose as a source of formate, DCCD-independent proton efflux was ∼2.5 mmol min−1, while a mutant lacking FocA showed only DCCD-inhibited, FOF1-ATPase-dependent proton-efflux. A strain synthesizing a chromosomally-encoded FocAH209N variant that functions exclusively to translocate formic acid out of the cell, showed a further 20 % increase in FocA-dependent proton efflux relative to the parental strain. Cells synthesizing a FocAT91A variant, which is unable to translocate formic acid out of the cell, showed only DCCD-inhibited proton efflux. When exogenous formate was added, formic acid uptake was shown to be both FocA- and proton motive force-dependent. By measuring rates of H2 production, potassium ion flux and ATPase activity, these data support a role for coupling between formate, proton and K+ ion translocation in maintaining pH and ion gradient homeostasis during fermentation. FocA thus plays a key role in maintaining this homeostatic balance in fermenting cells by bidirectionally translocating formic acid.

Uranium versus Thorium: A Case Study on a Base-Free Terminal Uranium Imido Metallocene.

The structure of and bonding in two base-free terminal actinide imido metallocenes, [η5-1,2,4-(Me3C)3C5H2]2An═N(p-tolyl) (An = U (1), Th (1')) are compared and connected to their individual reactivity. While structurally rather similar, the U(IV) derivative 1 is slightly more sterically crowded. Furthermore, density functional theory (DFT) studies imply that the 5f orbital contribution to the bonding within the individual actinide imido An═N(p-tolyl) moieties is significantly larger for 1 than for 1', which makes the bonds between the [η5-1,2,4-(Me3C)3C5H2]2U2+ and [(p-tolyl)N]2- fragments more covalent. Therefore, steric and electronic factors impact the reactivity of these imido complexes. For example, complex 1 is inert toward internal alkynes, but it readily forms Lewis base adducts [η5-1,2,4-(Me3C)3C5H2]2U═N(p-tolyl)(L) (L = OPMe3 (6), dmap (9), PhCN (14), and 2,6-Me2PhNC (17)) with Me3PO, 4-dimethylaminopyridine (dmap), nitrile, PhCN, or isonitrile 2,6-Me2PhNC. It may also react as a nucleophile or undergo a [2 + 2] cycloaddition with CS2, isothiocyanates, thio-ketones, ketones, lactides, and acyl nitriles, forming the four- or five-membered metallaheteroacycles, terminal sulfido, or oxido complexes, and cyanide amidate complexes, respectively. In contrast, after the addition of aldehyde p-tolylCHO, the tetranuclear complex [η5-1,2,4-(Me3C)3C5H2]4[OCH(p-tolyl)CH(p-tolyl)O]2U4O4 (10) is isolated. However, while 1 is unreactive toward dicyclohexylcarbodiimide (DCC), an equilibrium exists in benzene solution between N,N'-diisopropylcarbodiimide (DIC), 1, and the four-membered metallaheterocycle [η5-1,2,4-(Me3C)3C5H2]2U[N(p-tolyl)C(═NiPr)N(iPr)] (12). Furthermore, 1 may also engage in single- and two-electron transfer processes. It is singly oxidized by Ph3CN3, CuI, Ph2S2, and Ph2Se2, yielding the uranium(V) imido complexes [η5-1,2,4-(Me3C)3C5H2]2U═N(p-tolyl)(X) (X = N3 (20), I (22), PhS (23), and PhSe (24)), or is doubly oxidized by organic azides (RN3) and 9-diazofluorene, forming the uranium(VI) bis-imido metallocenes [η5-1,2,4-(Me3C)3C5H2]2U═N(p-tolyl)(=NR) (R = p-tolyl (18), mesityl (19)) and [η5-1,2,4-(Me3C)3C5H2]2U=N(p-tolyl)[=NN=(9-C13H8)] (21), respectively.

Relationship between proton/ potassium fluxes and central carbon catabolic pathways in different Saccharomyces cerevisiae strains under osmotic stress conditions

Ion homeostasis is pivotal for numerous cellular functions and adaptation. Investigation of the relationship between K+ and H+ transporters and energy exchange processes of S. cerevisiae ATCC 9804 and ATCC 13007 strains will be crucial to enhance resistance to osmotic stress and improve industrial processes. Specific growth rate (SGR), pH and oxidation-reduction potential (ORP), K+ and H+ fluxes, mitochondrial H+-ATPase activity changes, and metabolites were studied in physiological and osmotic stress conditions. Strictly neutral conditions are needed for yeast biomass production under osmotic stress (microaerophilic growth), where the SGR of ATCC 9804 is suppressed ∼85% and in ATCC 13007 ∼60% compared to physiological conditions. The addition of N′N’-dicyclohexylcarbodiimide (DCCD) completely abolishes K+ and H+ transport. High affinity to K+ ions were registered in aerobic growth, which decreased during the transition to microaerophilic growth, as well as under stress, and was especially low in DCCD-inhibited samples. Mitochondrial H+-ATPase activity was suppressed ∼5-fold under osmotic stress conditions, compared with the physiological one. Taken together it can be concluded that cell membrane transporters and the mitochondrial proton-potassium exchange systems, are crucial in maintaining cell physiological functions, regulating the energy balance via FOF1-ATPase, as well as in stress responding processes.

Synthesis of 1-(4-Bromobenzoyl)-1,3-dicyclohexylurea and Its Arylation via Readily Available Palladium Catalyst-Their Electronic, Spectroscopic, and Nonlinear Optical Studies via a Computational Approach.

In this study, we reported the synthesis of 1-(4-bromobenzoyl)-1,3-dicyclohexylurea by the reaction of DCC (N,N'-dicyclohexylcarbodiimide) with 4-bromobenzoic acid. Subsequently, we further synthesized a new series of 1-(4-arylbenzoyl)-1,3-dicyclohexylurea (5a-g) derivatives using a Suzuki cross-coupling reaction between 1-(4-bromobenzoyl)-1,3-dicyclohexylurea (3) and various aryl/heteroaryl boronic acids (4). Thus, density functional theory (DFT) calculations have been performed to examine the electronic structure of the synthesized compounds (3, 5a-g) and to calculate their spectroscopic data. Moreover, optimized geometries and thermodynamic properties, such as frontier molecular orbitals (HOMO, LUMO), molecular electrostatic potential surfaces, and reactivity descriptors, were also calculated at the PBE0-D3BJ/def2-TZVP/SMD1,4-dioxane level of theory to validate the structures of the synthesized compounds.

Diverse Reactions of α-Diimine-Ligated MgI -MgI -Bonded Compound with Carbodiimides.

The α-diimine-ligated dimagnesium(I) compound [K(thf)3 ]2 [LMg-MgL] (1, L=[(2,6-iPr2 C6 H3 )NC(Me)]2 2- ) displays diverse reactivities toward carbodiimides (RN=C=NR) with different R substituents. In the reaction of 1 with Me3 SiNCNSiMe3 , one of the easily leaving trimethylsilyl groups is lost to yield the Me3 SiNCN- moiety that either bridges two MgII centers (2) or terminally coordinated (3). In contrast, with the similarly bulky tBuNCNtBu, the carbodiimide inserts into Mg-Mg bond with accompanying C-H activation of a ligand or solvent (products 4 and 5). In the case of dicyclohexyl or diisopropyl carbodiimide, reductive C-C coupling of two RNCNR molecules occurs to form the [C2 (NR)4 ]2- diamido moiety, which bridges two Mg centers, giving complexes [{K(dme)2 }2 LMg(μ-{C2 (NR)4 })MgL] (6, R=Cy; 7, R=iPr) and [L⋅- Mg(μ-{C2 (NR)4 })MgL⋅- ] (8). Most interestingly, upon treating 1 with Me3 SiC≡CSiMe3 , the acetylide complex [K(dme)][LMg(C≡CSiMe3 )(dme)] (9) was prepared, which undergoes a rare "double insertion" with CyNCNCy to afford [K(solv)][K(dme)2 LMg(NCy)2 C-C≡C-C(NCy)2 MgL] (10) containing an acetylenediide-coupled bis(amidinate) ligand that bridges two Mg atoms.

Dicyclohexylcarbodiimide and disodium succinate regulate the browning development in fresh longan pericarp by modulating the antioxidant system and the metabolisms of membrane lipids and phenolics

In this study, the effects of dicyclohexylcarbodiimide (DCC) and disodium succinate (DS) treatments on the pericarp browning (PB) development in postharvest longan were elucidated by measuring PB-related phenotypes and the metabolisms of antioxidants, membrane lipids, and phenolics. Compared to the control, DCC-treated longan displayed the higher levels of PB index, CMP, ROS, PA, DAG, and SFAs, the higher activities of POD, PPO, and MLMEs including PLD, PC-PLC, PI-PLC, lipase, and LOX, and the higher expression levels of DlPPO1, DlPOD1, and genes encoding MLMEs. In contrast, the lower levels of chromaticity values, pigments, TP, PC, PI, and USFAs, the lower activities of RSEs including SOD, CAT, and APX, the lower expression levels of genes encoding RSEs, and a lower non-enzymatic antioxidant capacity were also noted in DCC-treated longan. These results imply that the exacerbated PB induced by DCC was associated with the activation of MLMEs by up-regulating the expression of genes encoding MLMEs, which expedited the damage of cell membrane. This membrane damage was also regulated by the accelerated accumulation of ROS triggered by DCC. The increased membrane permeability after the damage prompted an enzymatic oxidation between phenol oxidase and phenolics. However, the opposite effect occurred in the DS-treated longan.

Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

AbstractIn this work, we report the synthesis of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives based on acylated thioureas. The method for the preparation of 1,3,5‐oxadiazine derivatives is based on the reaction of dehydrosulfurization of the starting acylated thioureas under the action of dicyclohexylcarbodiimide (DCC) followed by the [4 + 2] cycloaddition reaction of another DCC molecule to the resulting intermediate carbodiimide. The structure of the obtained derivatives of 1,3,5‐oxadiazine was confirmed by 1H, 13C NMR, IR spectroscopy, mass spectrometry, and x‐ray diffraction analysis.

Post-synthetic modification of Zr-MOFs using guanidine for cyclic carbonate formation catalysis

A post-synthetic modification of Zr-MOF using ionic nitrogen-based functional groups is proposed for the catalytic cycloaddition reaction of CO2 with epoxides. Herein, guanidinium salt derivatives are used as ionic liquid (IL) catalysts while MOFs are used as a superior absorbent for CO2, allowing the generation of heterogeneous catalysts for CO2 fixation reactions under mild conditions. The UiO66-NH2 and UiO67-NH2 were functionalized with carbodiimides N,N′-dicyclohexylcarbodiimide (DCC) and N,N′-diisopropylcarbodiimide (DIC) to produce cationic guanidinium-containing Zr-MOFs with free bromide ions UiO66-DCCBr, UiO66-DICBr, and UiO67-DICBr. The materials were characterized comprehensively by multiple techniques such as PXRD, FTIR, TGA, SEM, EDS, 1H NMR, 13C NMR, elemental analysis, as well as N2 and CO2 adsorption equilibrium measurements. UiO66-DCCBr showed a high TOF for the formation of cyclic carbonates using several small epoxides under mild conditions (0.5 MPa CO2, 90 °C, without co-catalyst and solvent). In addition, UiO67- DICBr owing to the larger aperture size of MOF displayed better catalytic performance for the conversion of larger epoxides than UiO66-DICBr and UiO66-DCCBr with high yield and selectivity. This result underlines the important role of MOF’s aperture size for the diffusion of substrates in CO2 fixation reactions.