Skip to main content
Log in

Ecofriendly Approach for the Determination of Selected Aldehydes by Fluorescence Quenching of L-Tryptophan

  • Research
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

It is a fluorescence-based study to examine the interaction between L-tryptophan and a selection of aldehydes, namely furfural (furan-2-carbaldehyde), 3-hydroxybenzaldehyde, salicylaldehyde (2-hydroxybenzaldehyde), 3-nitrobenzaldehyde, and 4-bromobenzaldehyde. The investigation took place in an aqueous environment, revealing that all five aldehydes induced quenching of the fluorescence intensity of L-tryptophan. By employing the Stern-Volmer equation to describe the quenching process, we constructed Stern-Volmer plots and derived Stern-Volmer constants. These constants (KSV) ranged from 2.87 × 104 mol L− 1 to 5.75 × 104 mol L− 1. Notably, the values of the Stern-Volmer constants varied among the different aldehydes, with the following order: 3-hydroxybenzaldehyde(3-HBA) > 4-bromobenzaldehyde (4-BBA) > 3-nitrobenzaldehyde > furan-2-carbaldehyde > salicylaldehyde. Consequently, our findings highlighted 3-hydroxybenzaldehyde as the most potent quencher, while 2-hydroxybenzaldehyde displayed the least sensitivity to quenching. Additionally, we determined the detection and quantification limits for the investigated aldehydes, resulting in ranges of 3.87 × 10− 12 to 8.25 × 10− 6 and 1.29 × 10− 11 to 2.75 × 10− 5, respectively. This research paves the way for the development of novel fluorescence probe-based sensors and offers valuable techniques for analyzing aldehydes within environmental and biological samples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Data Availability

Data has been included in the manuscript, though if the spectra of all the experiments performed was needed will be sent on request.

References

  1. Basketter DA, Wright ZM, Warbrick EV, Dearman RJ, Kimber I, Ryan CA, Gerberick GF, White IR (2001) Human potency predictions for aldehydes using the local lymph node assay. Contact Derm 452:89–94. https://doi.org/10.1034/j.1600-0536.2001.045002089.x

    Article  Google Scholar 

  2. Araki A, Ketema RM, Ait Bamai Y, Kishi R (2020) Aldehydes, volatile organic compounds (VOCS), and health. Indoor environmental quality and health risk toward healthier environment for all. Curr Top Environ Health Prev Med 129–158. https://doi.org/10.1007/978-981-32-9182-9_7

  3. Britton LG (1998) Flammability hazards of lower aliphatic aldehydes at elevated pressure and temperature. Process Saf Prog 17:138–148. https://doi.org/10.1002/prs.680170211

    Article  CAS  Google Scholar 

  4. Domaille DW, Que EL, Chang CJ (2008) Synthetic fluorescent sensors for studying the cell biology of metals. Nat Chem Biol 4:168–175. https://doi.org/10.1038/nchembio.69

    Article  CAS  PubMed  Google Scholar 

  5. Klager S, Vallarino J, MacNaughton P, Christiani DC, Lu Q, Allen JG (2017) Flavoring chemicals and aldehydes in e-cigarette emissions. Environ Sci Technol 51:10806–10813. https://doi.org/10.1021/acs.est.7b02205

    Article  CAS  PubMed  Google Scholar 

  6. Eisler R (2000) Handbook of chemical risk assessment: health hazards to humans, plants, and animals, three volume set

  7. Lee S, Kim M, Ahn BJ, Jang Y (2023) Odorant-responsive biological receptors and electronic noses for volatile organic compounds with aldehyde for human health and diseases: a perspective review. J Hazard Mater 5:455: 131555. https://doi.org/10.1016/j.jhazmat.2023.131555

    Article  CAS  Google Scholar 

  8. Strasburg GM, Ludescher RD (1995) Theory and applications of fluorescence spectroscopy in food research. Trends Food Sci Technol 63:69–75. https://doi.org/10.1016/S0924-2244(00)88966-9

    Article  Google Scholar 

  9. Murphy KR, Stedmon CA, Graeber D, Bro R (2013) Fluorescence spectroscopy and multi-way techniques. PARAFAC Anal Methods 523:6557–6566

    Article  Google Scholar 

  10. Ladokhin AS (2000) Fluorescence spectroscopy in peptide and protein analysis. Encyclopedia of Analytical Chemistry 5762–5779. https://doi.org/10.1002/9780470027318.a1611

  11. Royer CA (1995) Fluorescence spectroscopy. Protein stability and folding: Theory and practice 65–89

  12. Raja TN, Brouwer AM (2011) Fluorescence spectroscopy in Polymer Science. https://doi.org/10.1007/978-3-642-18035-4_3

  13. Carstea EM, Bridgeman J, Baker A, Reynolds DM (2016) Fluorescence spectroscopy for wastewater monitoring: a review water res 95: 205 – 19. https://doi.org/10.1016/j.watres.2016.03.021

  14. Christensen J, Becker EM, Frederiksen C (2005) Fluorescence spectroscopy and PARAFAC in the analysis of yogurt. Chemom Inntel Lab Syst 752:201–208. https://doi.org/10.1016/j.chemolab.2004.07.007

    Article  CAS  Google Scholar 

  15. De Souza Sierra MM, Donard OFX, Lamotte M, Belin C, Ewald M (1994) Fluorescence spectroscopy of coastal and marine waters. Mar Chem 47:127–144. https://doi.org/10.1016/0304-4203(94)90104-X

    Article  Google Scholar 

  16. Coble PG, Green SA, Blough NV, Gagosian RB (1990) Characterization of dissolved organic matter in the black sea by fluorescence spectroscopy. Nature 348:432–435. https://doi.org/10.1038/348432a0

    Article  CAS  Google Scholar 

  17. Carter KP, Young AM, Palmer AE (2014) Fluorescent sensors for measuring metal ions in living systems. Chem Rev 114:4564–4601. https://doi.org/10.1021/cr400546e

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Burnworth M, Rowan SJ, Weder C (2007) Fluorescent sensors for the detection of chemical warfare agents. Chemistry 13:7828–7836. https://doi.org/10.1002/chem.200700720

    Article  CAS  PubMed  Google Scholar 

  19. Idrees M, Hussain S, Salam A (2023) Development of a sensitive and selective method for the determination of some selected aldehydes based on fluorescence quenching. J Fluoresc. https://doi.org/10.1007/s10895-023-03219-x

    Article  PubMed  Google Scholar 

  20. Idrees M, Bibi R, Khan MN (2018) Phenanthrene fluorescence quenching in aqueous sodium dodecyl sulphate (SDS) and determination of important metal ions. J Fluoresc 28:1251–1254. https://doi.org/10.1007/s10895-018-2288-2

    Article  CAS  PubMed  Google Scholar 

  21. Khan MN, Zaman N, Mursaleen M, Naz F, Ullah Z (2022) Eco-friendly approach for determination of moxifloxacin in pharmaceutical preparations and biological fluids through fluorescence quenching of eosin Y. Anal Sci 38:1541–1547. https://doi.org/10.1007/s44211-022-00192-6

    Article  CAS  PubMed  Google Scholar 

  22. Khan MN, Jan MN, Ullah Z (2023) Environmentally friendly protocol for the determination of sitagliptin phosphate in pharmaceutical preparations and biological fluids using l-tyrosine as a fluorescence probe. Luminescence. https://doi.org/10.1002/bio.4567

    Article  PubMed  Google Scholar 

  23. Farid NA, Youssef NF, Abdellatef HE, Sharaf YA (2023) Spectrofluorimetric methods for the determination of mirabegron by quenching tyrosine and L-tryptophan fluorophores: Recognition of quenching mechanism by stern Volmer relationship, evaluation of binding constants and binding sites. Spectrochim Acta A Mol Biomol Spectrosc 15:122473. https://doi.org/10.1016/j.saa.2023.122473

    Article  CAS  Google Scholar 

  24. Gong AQ, Zhu XS (2013) Determination of epristeride by its quenching effect on the fluorescence of L-tryptophan. J Pharm Anal 3:415–420. https://doi.org/10.1016/j.jpha.2013.05.001

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Idrees M, Ayaz M, Bibi R, Khan MN (2020) Fluorescence quenching of the probes L-tryptophan and indole by anions in aqueous system. Anal Sci 36:183–185. https://doi.org/10.2116/analsci.19P264

    Article  CAS  PubMed  Google Scholar 

  26. Kishikawa N, El-Maghrabey MH, Kuroda N (2019) Chromatographic methods and sample treatment techniques for aldehydes determination in biological, food, and environmental samples. J Pharm Biomed Anal 112782. https://doi.org/10.1016/j.jpba.2019.112782

Download references

Acknowledgements

The authors thank Allama Iqbal Open University Islamabad, Pakistan, for its assistance.

Funding

The authors declare that no funds were received during the preparation of this manuscript.

Author information

Authors and Affiliations

Authors

Contributions

Syeda Qandeel Wajid Kazmi prepared all the solutions, performed the experiment, and write the first draft of the manuscript. Muhammad Naeem Khan participated in the study design, the result and discussion, manuscript preparation, revision, and submission.

Corresponding author

Correspondence to Muhammad Naeem Khan.

Ethics declarations

Consent for Publication

The corresponding author on behalf of all the authors authorizes the publishers to publish the data after acceptance.

Consent to Participate

Not Applicable.

Ethics Declaration Statement

Not applicable.

Competing Interests

The authors declare no competing interests.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary Material 1

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khan, M.N., Kazmi, S.Q.W. Ecofriendly Approach for the Determination of Selected Aldehydes by Fluorescence Quenching of L-Tryptophan. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03456-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10895-023-03456-0

Keywords

Navigation