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Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates

  • Vikas S Padalkar , Vikas S. Patil , Rahul D. Telore and Nagaiyan Sekar EMAIL logo
Published/Copyright: August 1, 2012
Heterocyclic Communications
From the journal Heterocyclic Communications Volume 18 Issue 3

Abstract

Cyanuric chloride was allowed to react with N,N-diethylaniline to obtain 4-(4,6-dichloro-1,3,5-triazin-2-yl)-N,N-diethylaniline, which was converted into six novel 1,3,5-trisubstituted triazine derivatives on reaction with different amino acids. These compounds had UV absorption in the range 352–379 nm, accompanied by intense single emission in the range 420–497 nm with fairly good quantum yield (0.106–0.383). The new compounds were characterized by FT-IR, 1H NMR, 13C NMR, mass spectral, and elemental analyses. These fluorophores were conjugated with protein bovine serum albumin through carbodiimide chemistry between the negatively charged carboxylate groups (-COO-) of the fluorophore and the surface terminated positively charged amino groups (-NH3+) of the protein. The interaction between functionalized amino acids with protein molecules was investigated using fluorescence spectroscopy showing fluorescence enhancement or quenching of the fluorophore after conjugation.

Keywords: α-amino acid; bioconjugation; bovine serum albumin (BSA); fluorescence; 1,3,5-triazine
Corresponding author: Nagaiyan Sekar, Institute of Chemical Technology (Formerly UDCT), N.P. Marg, Matunga, Mumbai 400 019, Maharashtra, India

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Received: 2012-02-03
Accepted: 2012-04-02
Published Online: 2012-08-01
Published in Print: 2012-08-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

Articles in the same Issue

  1. Supplementary data
  2. Masthead
  3. Masthead
  4. Preliminary Communications
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https://doi.org/10.1515/hc-2012-0024
Keywords for this article
α-amino acid; bioconjugation; bovine serum albumin (BSA); fluorescence; 1,3,5-triazine

Articles in the same Issue

  1. Supplementary data
  2. Masthead
  3. Masthead
  4. Preliminary Communications
  5. Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
  6. Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
  7. Research Articles
  8. Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
  9. Efficient synthesis of selected phthalazine derivatives
  10. Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
  11. Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
  12. Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
  13. Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
  14. Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
  15. One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
  16. Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects
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