A new 5-bromoindolehydrazone anchored diiodosalicylaldehyde derivative as efficient fluoro and chromophore for selective and sensitive detection of tryptamine and F- ions: Applications in live cell imaging

Krishnaveni Karuppiah; Malini Nelson; M Mujahid Alam; Manickam Selvaraj; Murugesan Sepperumal; Siva Ayyanar

doi:10.1016/j.saa.2021.120777

A new 5-bromoindolehydrazone anchored diiodosalicylaldehyde derivative as efficient fluoro and chromophore for selective and sensitive detection of tryptamine and F^- ions: Applications in live cell imaging

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Mar 15:269:120777. doi: 10.1016/j.saa.2021.120777. Epub 2021 Dec 17.

Authors

Krishnaveni Karuppiah¹, Malini Nelson¹, M Mujahid Alam², Manickam Selvaraj³, Murugesan Sepperumal¹, Siva Ayyanar⁴

Affiliations

¹ Supramolecular and Organometallic Chemistry Laboratory, Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India.
² Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia.
³ Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia. Electronic address: mselvaraj@kku.edu.sa.
⁴ Supramolecular and Organometallic Chemistry Laboratory, Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India. Electronic address: drasiva@gmail.com.

PMID: 34954479
DOI: 10.1016/j.saa.2021.120777

Abstract

A novel indole hydrazone tagged moiety, 2-((5-bromo-1H-indol-2-yl) methylene) hydrazono) methyl)-4, 6-diiodophenol (BHDL) has been developed for the selective and sensitive detection of biogenic tryptamine and F^- ions. The binding dexterity of probe BHDL towards F^-/tryptamine (TryptA) has been investigated by UV-visible/fluorescence spectroscopy. In the presence of TryptA, probe exhibits strong enhancement in the emission band at 433 nm and the band at 555 nm underwent a blue shift accompanied by a decrease in intensity by the inhibition of Excited State Intramolecular Proton Transfer (ESIPT) on BHDL. Excitingly, complexation with F^- ions as well triggers an enhancement in a fluorescence band at 430 nm with the concomitant disappearance of the emission band at 555 nm due to the inhibition of ESIPT and deprotonation process initiated by the hydrogen bonding complex formation. Further, Density Functional Theoretical (DFT) calculations have been performed to support the mechanism functioned on the probe BHDL in the presence of TryptA/F^-.

Keywords: Cell imaging; Chemosensor; ESIPT; Fluoride ion; Tryptamine.

MeSH terms

Fluorescent Dyes*
Hydrogen Bonding
Protons*
Spectrometry, Fluorescence
Tryptamines

Substances

Fluorescent Dyes
Protons
Tryptamines