Catalog No.GC20137

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5-Fluoroindole Chemical Structure

Cas No.:399-52-0

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Chemical Properties

Cas No. 399-52-0 SDF
Formula C8H6FN M.Wt 135.14
Solubility Storage RT
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Research Update

5-Fluoroindole resistance identifies tryptophan synthase beta subunit mutants in Arabidopsis thaliana

Genetics 1995 May;140(1):303-13.PMID:7635295DOI:10.1093/genetics/140.1.303.

A study of the biochemical genetics of the Arabidopsis thaliana tryptophan synthase beta subunit was initiated by characterization of mutants resistant to the inhibitor 5-Fluoroindole. Thirteen recessive mutations were recovered that are allelic to trp2-1, a mutation in the more highly expressed of duplicate tryptophan synthase beta subunit genes (TSB1). Ten of these mutations (trp2-2 through trp2-11) cause a tryptophan requirement (auxotrophs), whereas three (trp2-100 through trp2-102) remain tryptophan prototrophs. The mutations cause a variety of changes in tryptophan synthase beta expression. For example, two mutations (trp2-5 and trp2-8) cause dramatically reduced accumulation of TSB mRNA and immunologically detectable protein, whereas trp2-10 is associated with increased mRNA and protein. A correlation exists between the quantity of mutant beta and wild-type alpha subunit levels in the trp2 mutant plants, suggesting that the synthesis of these proteins is coordinated or that the quantity or structure of the beta subunit influences the stability of the alpha protein. The level of immunologically detectable anthranilate synthase alpha subunit protein is increased in the trp2 mutants, suggesting the possibility of regulation of anthranilate synthase levels in response to tryptophan limitation.

Modulation of the La/Lb Mixing in an Indole Derivative: A Position-Dependent Study Using 4-, 5-, and 6-Fluoroindole

J Phys Chem A 2017 Mar 2;121(8):1597-1606.PMID:28140598DOI:10.1021/acs.jpca.6b12605.

The lowest two electronically excited singlet states of indole and its derivatives are labeled as La or Lb, based on the orientation of the transition dipole moment (TDM) and the magnitude of the permanent electric dipole moment. Rotationally resolved electronic Stark spectroscopy in combination with high level ab initio calculations offers the possibility to determine these characteristics and thus the electronic nature of the excited states. In the present contribution this approach was pursued for the systems 4- and 6-fluoroindole and the results compared to the previously investigated system 5-Fluoroindole. Changing the position of the fluorine atom from 5 to 4 or 6 is accompanied by an increasing amount of La character in the S1 state. This dramatically influences the orientation of the TDM and erases its ability to be a reasonable identifier of the nature of the excited states for both molecules. However, for 4-fluoroindole, where the influence of the La is weak, the nature of the S1 state can still be assigned to be mainly Lb based on the excited state dipole moment. For 6-fluoroindole, this is not the case anymore, and the La/Lb nomenclature completely breaks down due to heavily mixed excited states.

Antibiofilm and Antivirulence Properties of Indoles Against Serratia marcescens

Front Microbiol 2020 Oct 30;11:584812.PMID:33193228DOI:10.3389/fmicb.2020.584812.

Indole and its derivatives have been shown to interfere with the quorum sensing (QS) systems of a wide range of bacterial pathogens. While indole has been previously shown to inhibit QS in Serratia marcescens, the effects of various indole derivatives on QS, biofilm formation, and virulence of S. marcescens remain unexplored. Hence, in the present study, we investigated the effects of 51 indole derivatives on S. marcescens biofilm formation, QS, and virulence factor production. The results obtained revealed that several indole derivatives (3-indoleacetonitrile, 5-Fluoroindole, 6-fluoroindole, 7-fluoroindole, 7-methylindole, 7-nitroindole, 5-iodoindole, 5-fluoro-2-methylindole, 2-methylindole-3-carboxaldehyde, and 5-methylindole) dose-dependently interfered with quorum sensing (QS) and suppressed prodigiosin production, biofilm formation, swimming motility, and swarming motility. Further assays showed 6-fluoroindole and 7-methylindole suppressed fimbria-mediated yeast agglutination, extracellular polymeric substance production, and secretions of virulence factors (e.g., proteases and lipases). QS assays on Chromobacterium violaceum CV026 confirmed that indole derivatives interfered with QS. The current results demonstrate the antibiofilm and antivirulence properties of indole derivatives and their potentials in applications targeting S. marcescens virulence.

Ground and electronically excited singlet-state structures of 5-Fluoroindole deduced from rotationally resolved electronic spectroscopy and ab initio theory

Chemphyschem 2012 Sep 17;13(13):3134-8.PMID:22730106DOI:10.1002/cphc.201200345.

The structure and electronic properties of the electronic ground state and the lowest excited singlet state (S(1)) of 5-Fluoroindole (5FI) were determined by using rotationally resolved spectroscopy of the vibration-less electronic origin of 5FI. From the parameters of the axis reorientation Hamiltonian, the absolute orientation of the transition dipole moment in the molecular frame was determined and the character of the excited state was identified as L(b).

Polymer-induced biofilms for enhanced biocatalysis

Mater Horiz 2022 Oct 3;9(10):2592-2602.PMID:35912866DOI:10.1039/d2mh00607c.

The intrinsic resilience of biofilms to environmental conditions makes them an attractive platform for biocatalysis, bioremediation, agriculture or consumer health. However, one of the main challenges in these areas is that beneficial bacteria are not necessarily good at biofilm formation. Currently, this problem is solved by genetic engineering or experimental evolution, techniques that can be costly and time consuming, require expertise in molecular biology and/or microbiology and, more importantly, are not suitable for all types of microorganisms or applications. Here we show that synthetic polymers can be used as an alternative, working as simple additives to nucleate the formation of biofilms. Using a combination of controlled radical polymerization and dynamic covalent chemistry, we prepare a set of synthetic polymers carrying mildly cationic, aromatic, heteroaromatic or aliphatic moieties. We then demonstrate that hydrophobic polymers induce clustering and promote biofilm formation in MC4100, a strain of Escherichia coli that forms biofilms poorly, with aromatic and heteroaromatic moieties leading to the best performing polymers. Moreover, we compare the effect of the polymers on MC4100 against PHL644, an E. coli strain that forms biofilms well due to a single point mutation which increases expression of the adhesin curli. In the presence of selected polymers, MC4100 can reach levels of biomass production and curli expression similar or higher than PHL644, demonstrating that synthetic polymers promote similar changes in microbial physiology than those introduced following genetic modification. Finally, we demonstrate that these polymers can be used to improve the performance of MC4100 biofilms in the biocatalytic transformation of 5-Fluoroindole into 5-fluorotryptophan. Our results show that incubation with these synthetic polymers helps MC4100 match and even outperform PHL644 in this biotransformation, demonstrating that synthetic polymers can underpin the development of beneficial applications of biofilms.


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