News Update on Hydroxynaphthalene Research: Sep – 2019

Bacterial communities degrading amino- and hydroxynaphthalene-2-sulfonates.

A 6-aminonaphthalene-2-sulfonic acid (6A2NS)-degrading mixed microorganism community was isolated from a sample of watercourse Elbe water. the entire degradation of this xenobiotic compound is also delineate by a mutualistic interaction of 2 genus Pseudomonas strains isolated from this culture. One strain, BN6, may conjointly grow on 6A2NS in monoculture, however, with accumulation of black polymers. This organism established the initial conversion of 6A2NS into 5-aminosalicylate (5AS) through regioselective attack of the hydrocarbon skeleton within the one,2-position. 5AS was all degraded by another member of the community, strain BN9. when prolonged adaptation of strain BN6 to growth on 6A2NS, this organism pronto regenerate all naphthalene-2-sulfonates with OH- or NH2-substituents within the 5-, 6-, 7-, or 8-position. The corresponding hydroxy- or aminosalicylates were excreted in ratio amounts, with the exception that the substance from 5A2NS chemical reaction wasn’t identical with 6AS. [1]

Genotoxic hazards of azo pigments and other colorants related to 1-phenylazo-2-hydroxynaphthalene

Azo pigments are used extensively as coloring agents in inks, paints and cosmetics. we’ve surveyed the literature for genotoxic and cancer knowledge on 9 colorants, that are structurally associated with 1-phenylazo-2-hydroxynaphthalene (C.I. Solvent yellow 14). C.I. Solvent yellow fourteen is metabolized by aerophilic and peroxidative enzymes. Metabolically activated C.I. Solvent yellow fourteen forms each RNA and desoxyribonucleic acid adducts. It induces liver nodules in rats upon oral administration. though there’s a combination of negative and positive findings in short-run tests and in animal cancer studies, C.I. Solvent yellow fourteen ought to be thought-about genotoxic. C.I. Pigment red three ought to be thought-about malignant neoplastic disease however is just sapless genotoxic. C.I. Solvent yellow seven, C.I. Pigment orange five, C.I. Pigment red four, and C.I. Pigment red twenty three ought to be thought-about genotoxic. [2]

13C NMR spectroscopic and AM1 study of the intramolecular proton transfer in anils of salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde

Tautomeric equilibria in intramolecularly chemical element secured Schiff bases is studied on the premise of resolution 13C proton magnetic resonance chemical shifts. Variable temperature proton magnetic resonance chemical analysis information and comparison with acceptable models show that whereas anils of salicaldehyde exist as phenoplast tautomers, those of 2-hydroxynaphthalene-1-carbaldehyde exist as equilibrium mixtures containing considerable amounts of each organic compound and keto tautomers, the latter being slightly predominant. AM1 results regarding the relative stability of tautomers area unit in sensible agreement with the proton magnetic resonance chemical analysis info. [3]

Design and synthesis of anticancer 1-hydroxynaphthalene-2-carboxanilides with a p53 independent mechanism of action

A series of 116 small-molecule 1-hydroxynaphthalene-2-carboxanilides was designed supported the fragment-based approach and was synthesized in keeping with the microwave-assisted protocol. The biological activity of all of the compounds was tested on human colon malignant neoplastic disease cell lines together with a deleted TP53 tumour suppressor. The mechanism of activity was studied in keeping with the p53 standing within the cell. many compounds unconcealed a decent to glorious activity that was almost like or higher than the quality antitumor medication. a number of these gave the impression to be additional active against the p53 null cells than their wild-type counterparts. Intercalating the properties of those compounds might be to blame for their mechanism of action. [4]

Computational Study on 4-Amino-3-Hydroxynaphthalene-1-Sulfonic Acid (AHNSA)

A machine study on 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA) has been dispensed to research formation of poly-(AHNSA), and to get binding structures and energies of AHNSA-Ephedrine and AHNSA-Caffeine complexes. For this purpose, the DFT/B3LYP/6-31G(D) and DFT/B3LYP/6-31+G(D) level of theories were used. These were investigated from analysis of their atomic charge distributions, total spin density, frontier molecular orbitals, electricity potential maps and calculations of binding energies. Results from analysis counsel that homo-polymerization of AHNSA ought to involve the molecular orbitals arising between radical cations shaped from the neutral compound. The ensuing information illustrated that the strategy was possible to be helpful for homo-polymerization of AHNSA. Calculated binding energies of AHNSA-Caffeine and AHNSA-Ephedrine complexes were -8.77 kcal mol-1 and -8.36 kcal mol-1, severally, that indicated that each complexes may be shaped. [5]


[1] Nörtemann, B., Baumgarten, J., Rast, H.G. and Knackmuss, H.J., 1986. Bacterial communities degrading amino-and hydroxynaphthalene-2-sulfonates. Appl. Environ. Microbiol., 52(5), (Web Link)

[2] Møller, P. and Wallin, H., 2000. Genotoxic hazards of azo pigments and other colorants related to 1-phenylazo-2-hydroxynaphthalene. Mutation Research/Reviews in Mutation Research, 462(1), (Web Link)

[3] Alarcón, S.H., Olivieri, A.C. and González-Sierra, M., 1994. 13 C NMR spectroscopic and AM1 study of the intramolecular proton transfer in anils of salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde. Journal of the Chemical Society, Perkin Transactions 2, (5), (Web Link)

[4] Design and synthesis of anticancer 1-hydroxynaphthalene-2-carboxanilides with a p53 independent mechanism of action
Ewelina Spaczyńska, Anna Mrozek-Wilczkiewicz, Katarzyna Malarz, Jiri Kos, Tomas Gonec, Michal Oravec, Robert Gawecki, Andrzej Bak, Jana Dohanosova, Iva Kapustikova, Tibor Liptaj, Josef Jampilek & Robert Musiol
Scientific Reportsvolume 9, Article number: 6387 (2019) (Web Link)

[5] Denbela, G. and M. Mohammed, A. (2017) “Computational Study on 4-Amino-3-Hydroxynaphthalene-1-Sulfonic Acid (AHNSA)”, International Research Journal of Pure and Applied Chemistry, 14(4), (Web Link)

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