Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290

Abstract

Different 9H-carbazole derivatives have been investigated within the last decades due to their broad range of pharmacological applications. While the metabolism of 9H-carbazole has previously been reported, nothing was known about the bacterial transformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole. Thus, for the first time, the bacterial biotransformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole was analyzed using biphenyl-grown cells of Ralstonia sp. strain SBUG 290 expressing biphenyl 2,3-dioxygenase. This strain accumulated 3-hydroxy-1,2,3,5,6,7,8,9-octahydrocarbazol-4-one and 6'-iminobicyclohexylidene-2',4'-dien-2-one as major products during the incubation with 2,3,4,9-tetrahydro-1H-carbazole. Carbazol-9-yl-methanol was verified as the primary oxidation product of 9-methyl-9H-carbazole. In addition, 9H-carbazol-1-ol, 9H-carbazol-3-ol, and 3-hydroxy-1,2,3,9-tetrahydrocarbazol-4-one where detected in lower concentrations during the transformation of carbazol-9-yl-methanol and 9-methyl-9H-carbazole. Products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, as well as (1)H and (13)C nuclear magnetic resonance analyses.

Inhibition of Human Topoisomerase II by N,N,N‐Trimethylethanammonium Iodide Alkylcarbazole Derivatives

“…Carbazoles are an important class of indole‐containing heterocycles with antitumor activities; they have also been shown to have antibacterial, anti‐inflammatory, psychotropic, and anti‐histamine properties . Some derivatives have shown interesting pharmaceutical properties, interfering with DNA‐dependent enzymes, such as topoisomerases I/II and telomerase, along with other targets such as cyclin‐dependent kinases and estrogen receptors.…”

Substrate‐Baited Nanoparticles: A Catch and Release Strategy for Enzyme Recognition and Harvesting

“…The model system employed to demonstrate this strategy for extraction of xenobiotic metabolizing enzymes utilized Pseudomonas resinovorans CA10. This specific bacterial strain is a source of heterocyclic aromatic degrading enzymes,18 a critical biotransformation for numerous bioremediation and natural product synthesis processes 19–25…”

Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: part I

“…Several 9H-carbazoles possess various pharmacological applications and also they are used in dyes-, insecticide-, and plastic industries. In addition, several derivatives of 1,2,3,4-tetrahydro-9H-carbazole and 9-methyl-9Hcarbazole have been known by their medicinal use as antitubercular, antifungal, antibacterial, β 3 -adrenoceptor agonists and anticancer activities [2][3][4] .…”