Cyclic Anhydrides Formed from 1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarboxylic Acid and1,3-Benzene-dicarboxylic Acids

Infrared spectroscopy and multinuclear (13C, 17O, and 119Sn NMR spectroscopy have been used to study the structure of bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids (1-C4H9)2. Sn(X(COO)2), where X = (CH2)n (n = 0-8), CH=CH (cis and trans) and C6H4 (ortho and para).The crystalline compounds are formed by linear or cyclic oligomers or polymers whose basic building units represent a grouping composed of the central tin atom substituted by two 1-butyl groups and coordinated with both oxygen atoms of two anisobidentate carboxylic groups derived from different molecules of a dicarboxylic acid. The environment of the tin atom has a shape of a trapezoidal bipyramid. When dissolvet in non-coordinating solvents, the compounds retain the oligomeric character with unchanged structure of environment of the central tin atom. In the media of coordinating solvents the bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids form complexes whose central hexacoordinated tin atom binds two molecules of the solvent trough their donor atoms. Carboxylic groups form monodenate linkages in these complexes.

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Pharmacological activity of new imidazole-4,5-dicarboxylic acid derivatives in dopaminergic transmission suppression ttests in mice and rats

Research Results in Pharmacology ◽

10.3897/rrpharmacology.6.57883 ◽

2020 ◽

Vol 6 (4) ◽

pp. 51-57

Author(s):

Ekaterina E. Yakovleva ◽

Eugeny R. Bychkov ◽

Maria M. Brusina ◽

Levon B. Piotrovsky ◽

Petr D. Shabanov

Keyword(s):

Locomotor Activity ◽

Dicarboxylic Acid ◽

Open Field ◽

Field Test ◽

Open Field Test ◽

Dicarboxylic Acids ◽

Dopaminergic Transmission ◽

Dose Dependent ◽

Derivatives Of ◽

Experimental Improvement

Objective: To study the antiparkinsonian activity of new 1,2-substituted imidazole-4,5-dicarboxylic acids in dopaminergic transmission suppression tests in mice and rats. Materials and methods: On a model of reserpine extrapyramidal disorders, the derivatives of imidazole-dicarboxylic acids (IEM2258, IEM2248, IEM2247) were injected into the lateral brain ventricles of the mice 30 minutes after injecting reserpine at the doses of 0.1–0.5 mmol. Locomotor activity was analyzed in the Open-field test 2 hours later. In the catalepsy model, the studied agents were injected, using a pre-implanted cannula, with a simultaneous intraperitoneal injection of haloperidol. The severity of catalepsy was assessed with the Morpurgo method. Amantadine was used as a comparator drug in all the tests. Results: It was shown that IEM2258 significantly increased the main indicators of locomotor activity in the Open-field test at all the studied doses. The value of the antiparkinsonian effect of IEM2258 at doses of 0.4–0.5 mmol significantly exceeded that of amantadine. The antiparkinsonian effect of IEM2247 was maximally expressed and was significantly different from those in the control and comparator group at doses of 0.2 and 0.3 mmol. For all the experimental groups, a significant decrease in the manifestations of catalepsy in comparison with control indexes was determined. Discussion: The results made it possible to suggest the involvement of imidazole-4,5-dicarboxylic acids derivatives in the process of experimental improvement of dopaminergic neuromodulation and efficiency in animals. Conclusion: The data showed a significant dose-dependent antiparkinsonian activity of new imidazole-4,5-dicarboxylic acid derivatives, which makes it promising to develop these agents and to further search for effective and safe antiparkinsonian drugs in this pharmacological class. Graphical abstract

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Two-dimensional metal-organic frameworks containing linear dicarboxylates

Acta Crystallographica Section B Structural Science ◽

10.1107/s0108768106033283 ◽

2006 ◽

Vol 62 (5) ◽

pp. 808-814 ◽

Cited By ~ 51

Author(s):

Samuel M. Hawxwell ◽

Harry Adams ◽

Lee Brammer

Keyword(s):

Dicarboxylic Acid ◽

Solvothermal Synthesis ◽

Interplanar Spacing ◽

Metal Organic Frameworks ◽

Dicarboxylic Acids ◽

Two Dimensional ◽

Secondary Building Units ◽

Metal Organic ◽

Gas Molecules ◽

Solvent Molecules

The solvothermal synthesis of four two-dimensional metal-organic frameworks containing linear dicarboxylic acids as ligands for ZnII centres is described. Zn(BDC)(DMF) [(1) where BDC = benzene-1,4-dicarboxylic acid; DMF = N,N-dimethylformamide] adopts a common paddlewheel motif leading to a 44 grid network, whereas Zn3(BDC)3(EtOH)2 (2), Zn3(BDC)3(H2O)2·4DMF (3) and Zn3(BPDC)3(DMF)2·4DMF (4) each form networks with the relatively uncommon 36 topology based upon Zn3(O2CR)6 secondary building units. All contain coordinated solvent molecules, namely DMF [(1) and (4)], ethanol (2) or H2O (3). Comparison of structures (2) and (3) illustrates a clay-like flexibility in interplanar spacing which sheds light on the ability of the Zn3(BDC)3 framework to undergo desolvation and uptake of small solvent and gas molecules.

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Engineering energetically efficient transport of dicarboxylic acids in yeast Saccharomyces cerevisiae

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.1900287116 ◽

2019 ◽

Vol 116 (39) ◽

pp. 19415-19420 ◽

Cited By ~ 14

Author(s):

Behrooz Darbani ◽

Vratislav Stovicek ◽

Steven Axel van der Hoek ◽

Irina Borodina

Keyword(s):

Saccharomyces Cerevisiae ◽

Dicarboxylic Acid ◽

Acid Production ◽

Dicarboxylic Acids ◽

Scale Production ◽

Protein Motif ◽

Yeast Saccharomyces Cerevisiae ◽

Organic Acid Production ◽

Cell Factories ◽

Voltage Dependent

Biobased C4-dicarboxylic acids are attractive sustainable precursors for polymers and other materials. Commercial scale production of these acids at high titers requires efficient secretion by cell factories. In this study, we characterized 7 dicarboxylic acid transporters in Xenopus oocytes and in Saccharomyces cerevisiae engineered for dicarboxylic acid production. Among the tested transporters, the Mae1(p) from Schizosaccharomyces pombe had the highest activity toward succinic, malic, and fumaric acids and resulted in 3-, 8-, and 5-fold titer increases, respectively, in S. cerevisiae, while not affecting growth, which was in contrast to the tested transporters from the tellurite-resistance/dicarboxylate transporter (TDT) family or the Na+ coupled divalent anion–sodium symporter family. Similar to SpMae1(p), its homolog in Aspergillus carbonarius, AcDct(p), increased the malate titer 12-fold without affecting the growth. Phylogenetic and protein motif analyses mapped SpMae1(p) and AcDct(p) into the voltage-dependent slow-anion channel transporter (SLAC1) clade of transporters, which also include plant Slac1(p) transporters involved in stomata closure. The conserved phenylalanine residue F329 closing the transport pore of SpMae1(p) is essential for the transporter activity. The voltage-dependent SLAC1 transporters do not use proton or Na+ motive force and are, thus, less energetically expensive than the majority of other dicarboxylic acid transporters. Such transporters present a tremendous advantage for organic acid production via fermentation allowing a higher overall product yield.

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Model for the aspartate proteinases. Hydrolysis of a distorted amide catalyzed by dicarboxylic acids capable of forming cyclic anhydrides

Journal of the American Chemical Society ◽

10.1021/ja00216a042 ◽

1988 ◽

Vol 110 (8) ◽

pp. 2625-2629 ◽

Cited By ~ 12

Author(s):

V. Somayaji ◽

Jeff. Keillor ◽

R. S. Brown

Keyword(s):

Dicarboxylic Acids ◽

Cyclic Anhydrides ◽

Hydrolysis Of

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Syntheses and Antibiotic Evaluation of 2-{[(2R,4R)-4-Carboxy-2-hydroxypyrrolidin-1-yl]carbonyl}benzene-1,5-dicarboxylic Acids and 2-Carbamoylbenzene-1,5-dicarboxylic Acid Analogues

International Journal of Medicinal Chemistry ◽

10.1155/2016/9346585 ◽

2016 ◽

Vol 2016 ◽

pp. 1-8

Author(s):

Abdulrazaq Tukur ◽

Isaac Asusheyi Bello ◽

Neil Anthony Koorbanally ◽

James Dama Habila

Keyword(s):

Antimicrobial Activity ◽

Dicarboxylic Acid ◽

Nucleophilic Addition ◽

Antimicrobial Agents ◽

Dicarboxylic Acids ◽

Biological Evaluation ◽

Zone Of Inhibition ◽

Inhibition Concentration ◽

New Antibiotics ◽

Vancomycin Resistant

Our search for new antibiotics led to the syntheses and biological evaluation of new classes of dicarboxylic acid analogues. The syntheses involve nucleophilic addition of different substituted benzylamine, aniline, alkylamine, and 4-hydroxyl-L-proline with carbamoylbenzoic acid. The results of the antimicrobial activity as indicated by the zone of inhibition (ZOI) showed that Z10 is the most active against Pseudomonas aeruginosa (32 mm) and least active against Candida stellatoidea (27 mm) and Vancomycin Resistant Enterococci (VRE) (27 mm), while Z7 shows the least zone of inhibition (22 mm) against Methicillin Resistant Staphylococcus aureus (MRSA). The minimum inhibition concentration (MIC) determination reveals that Z10 inhibits the growth of tested microbes at a low concentration of 6.25 μg/mL, while Z9 and Z12 inhibits the growth of most microbes at a concentration of 12.5 μg/mL, recording the least MIC. The Minimum Bactericidal/Fungicidal Concentration (MBC/MFC) results revealed that Z10 has the highest bactericidal/fungicidal effect on the test microbes, at a concentration of 12.5 μg/mL, with the exception of Candida stellatoidea and Vancomycin Resistant Enterococci (VRE) with MBC/MFC of 25 μg/mL. The result of this investigation reveals the potential of the target compounds (Z1–3,5,7–12) in the search for new antimicrobial agents.

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Intermediary metabolism of Acinetobacter grown on dialkyl ethers

Canadian Journal of Microbiology ◽

10.1139/m89-171 ◽

1989 ◽

Vol 35 (11) ◽

pp. 1031-1036 ◽

Cited By ~ 1

Author(s):

Malcolm C. Modrzakowski ◽

William R. Finnerty

Keyword(s):

Fatty Acids ◽

Dicarboxylic Acid ◽

Chain Length ◽

Dicarboxylic Acids ◽

Acid Oxidation ◽

Methyl Group ◽

Ether Oxygen ◽

Dialkyl Ethers ◽

Long Chain ◽

Methyl Group Oxidation

The microbial dissimilation of long-chain dialkyl ethers by Acinetobacter sp. H01-N involved a terminal methyl group oxidation of the dialkyl ether substrates, resulting in the formation of ether oxygen containing fatty acids of corresponding chain length. An internal carbon–carbon scission of the dialkyl ethers resulted in the formation of end-product ether fatty acids and corresponding dicarboxylic acids. Cellular carbon and energy were derived from the subsequent metabolism of the dicarboxylic acids. Dicarboxylic acid oxidation, activation, and identification of cellular dicarboxylic acids indicated dibasic acids as intermediates in the metabolism of dialkyl ethers.Key words: dialkyl ethers, dicarboxylic acids, fatty acids, Acinetobacter.

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New Substrates for the Dicarboxylate Transport System of Sinorhizobium meliloti

Journal of Bacteriology ◽

10.1128/jb.182.15.4216-4221.2000 ◽

2000 ◽

Vol 182 (15) ◽

pp. 4216-4221 ◽

Cited By ~ 21

Author(s):

Svetlana Yurgel ◽

Michael W. Mortimer ◽

Kimberly N. Rogers ◽

Michael L. Kahn

Keyword(s):

Dicarboxylic Acid ◽

Transport System ◽

Sinorhizobium Meliloti ◽

Monocarboxylic Acid ◽

Dicarboxylic Acids ◽

Carbonyl Groups ◽

Nitrogen Fixing ◽

Extended Conformation ◽

Dicarboxylate Transport ◽

Succinamic Acid

ABSTRACT The dicarboxylate transport (Dct) system of Sinorhizobium meliloti, which is essential for a functional nitrogen-fixing symbiosis, has been thought to transport only dicarboxylic acids. We show here that the permease component of the Dct system, DctA, can transport orotate, a monocarboxylic acid, with an apparentKm of 1.7 mM and a V maxof 163 nmol min−1 per mg of protein in induced cells. DctA was not induced by the presence of orotate. The transport of orotate was inhibited by several compounds, including succinamic acid and succinamide, which are not dicarboxylic acids. The dicarboxylic acid maleate (cis-butenedioic acid) was not an inhibitor of orotate transport, which suggests that it was not recognized by DctA. However, maleate was an excellent inducer of DctA expression. Our evaluation of 17 compounds as inducers and inhibitors of transport suggests that substrates recognized by S. meliloti DctA must have appropriately spaced carbonyl groups and an extended conformation, while good inducers are more likely to have a curved conformation.

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