Highly Sensitive Bifunctional Probe for Colorimetric Cyanide and Fluorometric H 2 S Detection and Bioimaging: Spontaneous Resolution, Aggregation, and Multicolor Fluorescence of Bisulfide Adduct

A 4-methylbenzothiazole linked maleimide-based single molecular bifunctional probe 1 has been synthesized for the colorimetric and fluorometric detection of highly competitive H S and cyanide ion in aqueous DMSO media. The probe 1 selectively detected CN under the UV-vis spectroscopy through the rap...

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Published inJournal of organic chemistry Vol. 82; no. 19; pp. 10234 - 10246
Main Authors Patra, Sumit Kumar, Sheet, Sanjoy Kumar, Sen, Bhaskar, Aguan, Kripamoy, Roy, Debesh Ranjan, Khatua, Snehadrinarayan
Format Journal Article
LanguageEnglish
Published United States 06.10.2017
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Abstract A 4-methylbenzothiazole linked maleimide-based single molecular bifunctional probe 1 has been synthesized for the colorimetric and fluorometric detection of highly competitive H S and cyanide ion in aqueous DMSO media. The probe 1 selectively detected CN under the UV-vis spectroscopy through the rapid appearance of deep pink color. The bright pink color developed due to ICT in the moderately stable cyano substituted enolate intermediate. The absorbance titration of 1 with CN revealed a new band at 540 nm and the nonlinear curve fitting analysis showed good fit with 1:1 model. In fluorescence channel, 1 was found to be highly selective to H S in 50% aqueous buffer (pH 7). It exhibited ∼16-fold fluorescence intensity enhancement at 435 nm after reaction with 1 equiv of H S due to the inhibition of PET. The 1-SH adduct showed TICT phenomenon and behaved like molecular rotor. It further displayed aggregation behavior at higher concentration and excitation wavelength dependent multicolor emission properties. Most interestingly, the spontaneous resolution of chiral S-isomer of the 1-SH adduct occurred during crystallization. The cell imaging study revealed the staining of the cell and multicolor emission in the presence of H S.
AbstractList A 4-methylbenzothiazole linked maleimide-based single molecular bifunctional probe 1 has been synthesized for the colorimetric and fluorometric detection of highly competitive H S and cyanide ion in aqueous DMSO media. The probe 1 selectively detected CN under the UV-vis spectroscopy through the rapid appearance of deep pink color. The bright pink color developed due to ICT in the moderately stable cyano substituted enolate intermediate. The absorbance titration of 1 with CN revealed a new band at 540 nm and the nonlinear curve fitting analysis showed good fit with 1:1 model. In fluorescence channel, 1 was found to be highly selective to H S in 50% aqueous buffer (pH 7). It exhibited ∼16-fold fluorescence intensity enhancement at 435 nm after reaction with 1 equiv of H S due to the inhibition of PET. The 1-SH adduct showed TICT phenomenon and behaved like molecular rotor. It further displayed aggregation behavior at higher concentration and excitation wavelength dependent multicolor emission properties. Most interestingly, the spontaneous resolution of chiral S-isomer of the 1-SH adduct occurred during crystallization. The cell imaging study revealed the staining of the cell and multicolor emission in the presence of H S.
Author Sheet, Sanjoy Kumar
Patra, Sumit Kumar
Roy, Debesh Ranjan
Aguan, Kripamoy
Khatua, Snehadrinarayan
Sen, Bhaskar
Author_xml – sequence: 1
  givenname: Sumit Kumar
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  fullname: Patra, Sumit Kumar
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  fullname: Sheet, Sanjoy Kumar
  organization: Centre for Advanced Studies, Department of Chemistry, North Eastern Hill University , Shillong, Meghalaya 793022, India
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  fullname: Sen, Bhaskar
  organization: Centre for Advanced Studies, Department of Chemistry, North Eastern Hill University , Shillong, Meghalaya 793022, India
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  givenname: Kripamoy
  surname: Aguan
  fullname: Aguan, Kripamoy
  organization: Department of Biotechnology and Bioinformatics, North Eastern Hill University , Shillong, Meghalaya 793022, India
– sequence: 5
  givenname: Debesh Ranjan
  surname: Roy
  fullname: Roy, Debesh Ranjan
  organization: Applied Physics Department, S.V. National Institute of Technology , Surat 395 007, India
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  orcidid: 0000-0003-0992-4800
  surname: Khatua
  fullname: Khatua, Snehadrinarayan
  organization: Centre for Advanced Studies, Department of Chemistry, North Eastern Hill University , Shillong, Meghalaya 793022, India
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28837340$$D View this record in MEDLINE/PubMed
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Snippet A 4-methylbenzothiazole linked maleimide-based single molecular bifunctional probe 1 has been synthesized for the colorimetric and fluorometric detection of...
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Title Highly Sensitive Bifunctional Probe for Colorimetric Cyanide and Fluorometric H 2 S Detection and Bioimaging: Spontaneous Resolution, Aggregation, and Multicolor Fluorescence of Bisulfide Adduct
URI https://www.ncbi.nlm.nih.gov/pubmed/28837340
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