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Vorob'ev AY, Dranova TY, Moskalensky AE. Photolysis of dimethoxynitrobenzyl-"caged" acids yields fluorescent products. Sci Rep. 2019;9(1):13421doi: 10.1038/s41598-019-49845-z.
Vorob'ev, A. Y., Dranova, T. Y., & Moskalensky, A. E. (2019). Photolysis of dimethoxynitrobenzyl-"caged" acids yields fluorescent products. Scientific reports, 9(1), 13421. https://doi.org/10.1038/s41598-019-49845-z
Vorob'ev, Aleksey Yu, et al. "Photolysis of dimethoxynitrobenzyl-"caged" acids yields fluorescent products." Scientific reports vol. 9,1 (2019): 13421. doi: https://doi.org/10.1038/s41598-019-49845-z
Vorob'ev AY, Dranova TY, Moskalensky AE. Photolysis of dimethoxynitrobenzyl-"caged" acids yields fluorescent products. Sci Rep. 2019 Sep 17;9(1):13421. doi: 10.1038/s41598-019-49845-z. PMID: 31530869; PMCID: PMC6748988.
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Sci Rep. 2019 Sep 17;9(1):13421. doi: 10.1038/s41598-019-49845-z.

Photolysis of dimethoxynitrobenzyl-"caged" acids yields fluorescent products.

Scientific reports

Aleksey Yu Vorob'ev, Tatyana Yu Dranova, Alexander E Moskalensky

Affiliations

  1. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, 9 Lavrentiev Ave, 630090, Novosibirsk, Russia.
  2. Novosibirsk State University, Pirogova 2, 630090, Novosibirsk, Russia.
  3. Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya str. 3, 630090, Novosibirsk, Russia.
  4. Novosibirsk State University, Pirogova 2, 630090, Novosibirsk, Russia. [email protected].
  5. Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya str. 3, 630090, Novosibirsk, Russia. [email protected].

PMID: 31530869 PMCID: PMC6748988 DOI: 10.1038/s41598-019-49845-z

Abstract

Carboxylic acids conjugated with 4,5-dimethoxy-2-nitrobenzyl photoremovable protecting group are well known and widely used for biological studies. In this paper, we study the photolysis of likewise "caged" acetic, caprylic and arachidonic acids. Unexpectedly, we observed huge growth of fluorescence emission at ~430 nm during photolysis. Following further UV irradiation, a product with fluorescence at longer wavelength was formed (470 nm excitation / ~500-600 nm emission). While it may be used to monitor the "uncaging", these fluorescent products may interfere with widespread dyes such as fluorescein in biomedical experiments. This effect might be negligible if the photolysis products dissolve in the medium. On the other hand, we observed that arachidonic and caprylic acids derivatives self-organize in emulsion droplets in water environment due to long lipophilic chains. Illumination of droplets by UV rapidly induces orange fluorescence excited by 488 nm light. This fluorescence turn-on was fast (~0.1 s) and apparently caused by the accumulation of water-insoluble fluorescent residuals inside droplets. These self-organized lipophilic structures with fluorescence turn-on capability may be of interest for biomedical and other application. We have identified and hypothesized some compounds which may be responsible for the observed fluorescense.

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