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Synthesis and Biological Evaluation of a Photoswitchable Quorum Sensing Molecule
Author(s) -
Karns Taylor,
Stajdl Shelby,
Zimmer Kassidy,
Rohlman Christopher,
Streu Craig
Publication year - 2019
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.2019.33.1_supplement.650.5
Subject(s) - quorum sensing , molecule , chemistry , biofilm , bacteria , photoisomerization , nanotechnology , combinatorial chemistry , biophysics , biochemistry , biology , materials science , organic chemistry , isomerization , genetics , catalysis
Quorum sensing is the ability of bacteria to communicate with one another via chemical signals. This ignites a response within the collective group of bacteria to produce a single response that ultimately benefits the bacteria, an example being biofilm formation. If this natural process could be controlled or coopted, the biotecnical applications arising from this natural ability of bacteria could be limitless. Photoswitching molecules are able to respond to a light stimiulus. Azostilbenes in particular isomerize from trans to the cis conformation in response to the appropriate wavelengths of light. If one of the available conformations is bioactive, while the other is not, this photoisomerization has the effect of activating or inactivating the molecule in response to light. The power of light responsive chemical signaling systems comes from their ability to achieve exquisite spatial and temporal control, which is of tremendous utility for numerous bioindustrial applications. To this end, we have designed a series of photoswitching molecules based upon N‐acyl homoserine lactones (AHLs), which are known to be prominent chemical messengers in numerous bacterial species, by integrating the azo‐stilbenoid motif into the parent molecule scaffold. These molecules are made by Mills coupling between the appropriate aniline and aryl‐nitroso species. Their photokinetic properties are measured by UV/Vis spectroscopy and their bioactivity measured in the presence and absence of isomerizing light. We herein describe the synthesis, photokinetic studies, and bioactivity of this class of photoswitchable molecule. We also describe potential industrial applications of this technology. Support or Funding Information Albion College Foundation for Undergraduate Research, Scholarship, and Creative Activity This abstract is from the Experimental Biology 2019 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .