A Novel Fluorescent Probe for the Detection of Cyanide Ions in Solutions and Studies on Its Biophysical Interactions with CtDNA and Proteases

Overview

Journal J Fluoresc

Specialties Biophysics
Chemistry

Date 2022 Aug 16

PMID 35972711

Authors

Bensu Doyuran

Elmas Gokoglu

Ayman Zouitini

Ergin Keles

Tugba Taskin-Tok

Nurgul Seferoglu

Zeynel Seferoglu

Affiliations

Soon will be listed here.

Abstract

A new cationic indolium based styryl dye (Ci) as a fluorescent probe was synthesized and its anions selectivity/sensitivity properties/molecular interactions with protease enzymes (pepsin/trypsin) and ctDNA has been studied by spectroscopic and computational methods. The fluorescence measurements at different temperatures indicated that quenching mechanism of enzymes by Ci was static. ΔH and ΔS data pointed out electrostatic/hydrophobic interactions with pepsin, and also hydrogen bonds/van der Waals forces with trypsin of Ci. According to Förster's non-radiative energy transfer, binding distances (r) were calculated as 3.53/3.27 nm for pepsin/trypsin. It was also investigated that groove binding is effective in interaction with ctDNA. The results were supported with molecular docking analyzes which have same tendency. Ci has been demonstrated hypsochromic effect with a decrease in polarity of solvents and it showed highly selective colorimetric and fluorometric sensing behavior for cyanide in organic solvent and in aqueous solution. H NMR titration was performed to examine the interaction mechanism between Ci and cyanide. The LOD values of cyanide ion were reported as 4.87 × 10 M and 9.70 × 10 M in DMSO and DMSO/HO binary mixture, respectively. In addition, sensitivity of Ci as a chemosensor to cyanide was investigated in bitter almond samples.

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References

Gu J, Anumala U, Monte F, Kramer T, Heyny von Haussen R, Holzer J . 2-Styrylindolium based fluorescent probes visualize neurofibrillary tangles in Alzheimer's disease. Bioorg Med Chem Lett. 2012; 22(24):7667-71. DOI: 10.1016/j.bmcl.2012.09.109. View

Promchat A, Rashatasakhon P, Sukwattanasinitt M . A novel indolium salt as a highly sensitive and selective fluorescent sensor for cyanide detection in water. J Hazard Mater. 2017; 329:255-261. DOI: 10.1016/j.jhazmat.2017.01.024. View

Wang S, Fei X, Guo J, Yang Q, Li Y, Song Y . A novel reaction-based colorimetric and ratiometric fluorescent sensor for cyanide anion with a large emission shift and high selectivity. Talanta. 2015; 148:229-36. DOI: 10.1016/j.talanta.2015.10.058. View

Liu J, Sun Y, Huo Y, Zhang H, Wang L, Zhang P . Simultaneous fluorescence sensing of Cys and GSH from different emission channels. J Am Chem Soc. 2013; 136(2):574-7. DOI: 10.1021/ja409578w. View

Yu Q, Yin Zhang K, Liang H, Zhao Q, Yang T, Liu S . Dual-emissive nanohybrid for ratiometric luminescence and lifetime imaging of intracellular hydrogen sulfide. ACS Appl Mater Interfaces. 2015; 7(9):5462-70. DOI: 10.1021/am5091534. View

Pinto M, Schanze K . Amplified fluorescence sensing of protease activity with conjugated polyelectrolytes. Proc Natl Acad Sci U S A. 2004; 101(20):7505-10. PMC: 419635. DOI: 10.1073/pnas.0402280101. View

Li X, Ni T . Binding of glutathione and melatonin to pepsin occurs via different binding mechanisms. Eur Biophys J. 2015; 45(2):165-74. DOI: 10.1007/s00249-015-1085-y. View

Botti V, Cesaretti A, Ban Z, Crnolatac I, Consiglio G, Elisei F . Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences. Org Biomol Chem. 2019; 17(35):8243-8258. DOI: 10.1039/c9ob01186b. View

Barman S, Das J, Biswas S, Maiti T, Singh N . A spiropyran-coumarin platform: an environment sensitive photoresponsive drug delivery system for efficient cancer therapy. J Mater Chem B. 2020; 5(21):3940-3944. DOI: 10.1039/c7tb00379j. View

10.

Rose Y, Duarte J, Lowe R, Segura J, Bi C, Bhikadiya C . RCSB Protein Data Bank: Architectural Advances Towards Integrated Searching and Efficient Access to Macromolecular Structure Data from the PDB Archive. J Mol Biol. 2020; 433(11):166704. PMC: 9093041. DOI: 10.1016/j.jmb.2020.11.003. View

11.

Morris G, Huey R, Lindstrom W, Sanner M, Belew R, Goodsell D . AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem. 2009; 30(16):2785-91. PMC: 2760638. DOI: 10.1002/jcc.21256. View

12.

Lakowicz J, Weber G . Quenching of fluorescence by oxygen. A probe for structural fluctuations in macromolecules. Biochemistry. 1973; 12(21):4161-70. PMC: 6959846. DOI: 10.1021/bi00745a020. View

13.

Mohseni-Shahri F, Moeinpour F, Nosrati M . Spectroscopy and molecular dynamics simulation study on the interaction of sunset yellow food additive with pepsin. Int J Biol Macromol. 2018; 115:273-280. DOI: 10.1016/j.ijbiomac.2018.04.080. View

14.

Li X, Geng M . Probing the binding of procyanidin B3 to trypsin and pepsin: A multi-technique approach. Int J Biol Macromol. 2016; 85:168-78. DOI: 10.1016/j.ijbiomac.2015.12.075. View

15.

Ross P, Subramanian S . Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry. 1981; 20(11):3096-102. DOI: 10.1021/bi00514a017. View

16.

Zeng H, Yang D, Hu G, Yang R, Qu L . Studies on the binding of pepsin with three pyrethroid insecticides by multi-spectroscopic approaches and molecular docking. J Mol Recognit. 2016; 29(10):476-84. DOI: 10.1002/jmr.2547. View

17.

Lian S, Wang G, Zhou L, Yang D . Fluorescence spectroscopic analysis on interaction of fleroxacin with pepsin. Luminescence. 2013; 28(6):967-72. DOI: 10.1002/bio.2469. View

18.

Zhang H, Zhou Q, Wang Y . Studies on the interactions of 2, 4-dinitrophenol and 2, 4-dichlorphenol with trypsin. J Fluoresc. 2009; 20(2):507-16. DOI: 10.1007/s10895-009-0574-8. View

19.

Matei I, Hillebrand M . Interaction of kaempferol with human serum albumin: a fluorescence and circular dichroism study. J Pharm Biomed Anal. 2009; 51(3):768-73. DOI: 10.1016/j.jpba.2009.09.037. View

20.

Li X, Ni T . Probing the binding mechanisms of α-tocopherol to trypsin and pepsin using isothermal titration calorimetry, spectroscopic, and molecular modeling methods. J Biol Phys. 2016; 42(3):415-34. PMC: 4942422. DOI: 10.1007/s10867-016-9415-6. View