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Selective Sensing of Iron by Pyrrolo[2,3-c]Quinolines

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Abstract

This paper reports development of an iron sensor, 2-(3H-pyrrolo[2,3-c]quinolin-4-yl)aniline (APQ). The fluorophore facilitates micromolar detection of Fe3+/Fe2+ in the presence of various cations, including well-known interfering cations Co2+and Cu2+ by the process of fluorescence quenching.

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References

  1. Fernandez-Real JM, McClain D, Manco M (2015) Mechanisms linking glucose homeostasis and iron metabolism toward the onset and progression of Type 2 diabetes. Diabetes Care 38:2169–2176

    Article  CAS  PubMed  Google Scholar 

  2. Rathnasamy G, Ling E-A, Kaur C (2013) Consequences of iron accumulation in microglia and its implications in neuropathological conditions. CNS Neurol Disord Drug Targets 12:785–798

    Article  CAS  PubMed  Google Scholar 

  3. Lushchak V, Semchyshyn H (eds) (2012) Oxidative stress: molecular mechanisms and biological effects. Intech. https://doi.org/10.5772/2333

  4. Youdim MBH (2008) Brain iron deficiency and excess; cognitive impairment and neurodegenration with involvement of striatum and hippocampus. Neurotox Res 14:45–56

    Article  CAS  PubMed  Google Scholar 

  5. Ohashi A, Ito H, Kanai C, Imura H, Ohashi K (2005) Cloud point extraction of iron(III) and vanadium(V) using 8-quinolinol derivatives and Triton X-100 and determination of 10moldm level iron(III) in riverine water reference by a graphite furnace atomic absorption spectroscopy. Talanta 65:525–530

    Article  CAS  PubMed  Google Scholar 

  6. Lunvongsa S, Oshima M, Motomizu S (2006) Determination of total and dissolved amount of iron in water samples using catalytic spectrophotometric flow injection analysis. Talanta 68:969–973

    Article  CAS  PubMed  Google Scholar 

  7. Gomes DMC, Segundo MA, Lima JLFC, Rangel AOSS (2005) Spectrophotometric determination of iron and boron in soil extracts using a multi-syringe flow injection system. Talanta 66:703–711

    Article  CAS  PubMed  Google Scholar 

  8. Tesfaldet ZO, van Staden JF, Stefan RI (2004) Sequential injection spectrophotometric determination of iron as Fe(II) in multi-vitamin preparations using 1,10-phenanthroline as complexing agent*1. Talanta 64:1189–1195

    Article  CAS  PubMed  Google Scholar 

  9. Yokoi K, Van den Berg CMG (1992) The determination of iron in seawater using catalytic cathodic stripping voltammetry. Electroanalysis 4:65–69

    Article  CAS  Google Scholar 

  10. Bobrowski A, Nowak K, Zarebski J (2005) Application of a bismuth film electrode to the voltammetric determination of trace iron using a Fe(III)–TEA–BrO3− catalytic system. Anal Bioanal Chem 382:1691–1697

    Article  CAS  PubMed  Google Scholar 

  11. Elrod VA, Johnson KS, Coale KH (1991) Determination of subnanomolar levels of iron(II) and total dissolved iron in seawater by flow injection and analysis with chemiluminescence detection. Anal Chem 63:893–898

    Article  CAS  Google Scholar 

  12. Qin W, Zhang ZJ, Zhang CJ (1998) Chemiluminescence flow sensor with immobilized reagents for the determination of iron(III). Microchim Acta 129:97–101

    Article  CAS  Google Scholar 

  13. Kimura M, Tsunenaga M, Takami S, Ohbayashi Y (2005) Development of Functional Imidazole Derivatives: A Potential Chemiluminescent Chemosensor. Bull Chem Soc Jpn 78:929–931

    Article  CAS  Google Scholar 

  14. Kikkeri R, Traboulsi H, Humbert N, Gumienna-Kontecka E, Arad-Yellin R, Melman G, Elhabiri M, Albrecht-Gary AM, Shanzer A (2007) Toward Iron Sensors: Bioinspired Tripods Based on Fluorescent Phenol-oxazoline Coordination Sites. Inorg Chem 46:2485–2497

    Article  CAS  PubMed  Google Scholar 

  15. Sahoo SK, Sharma D, Bera RK, Crisponi G, Callan JF (2012) Iron(III) selective molecular and supramolecular fluorescent probes. Chem Soc Rev 41:7195–7227

    Article  CAS  PubMed  Google Scholar 

  16. Lan L, Niu Q, Guo Z, Liu H, Li T (2017) Highly sensitive and fast responsive “turn-on” fluorescent sensor for selectively sensing Fe 3+ and Hg 2+ in aqueous media based on an oligothiophene derivative and its application in real water samples. Sensors Actuators B Chem 244:500–508

    Article  CAS  Google Scholar 

  17. Hua C, Zheng H, Zhang K, Xin M, Gao J, Li Y (2016) A novel turn off fluorescent sensor for Fe(III) and pH environment based on coumarin derivatives: the fluorescence characteristics and theoretical study. Tetrahedron 72:8365–8372

    Article  CAS  Google Scholar 

  18. Zhao B, Liu T, Fang Y, Wang L, Song B, Deng Q (2016) A novel colorimetric chemosensor based on quinoline for the sequential detection of Fe3+ and PPi in aqueous solution. Tetrahedron Lett 58:1025–1029

  19. Joshi S, Kumari S, Bhattacharjee R, Sarmah A, Sakhuja R, Pant DD (2015) Experimental and theoretical study: determination of dipole moment of synthesized coumarin–triazole derivatives and application as turn off fluorescence sensor: High sensitivity for iron(III) ions. Sensors Actuators B Chem 220:1266–1278

    Article  CAS  Google Scholar 

  20. Sharma D, Kuba A, Thomas R, Kumar R, Choi H-J, Sahoo SK (2016) An aqueous friendly chemosensor derived from vitamin B6 cofactor for colorimetric sensing of Cu2+ and fluorescent turn-off sensing of Fe3+. Spectrochim Acta A 153:393–396

    Article  CAS  Google Scholar 

  21. Maity S, Kundu A, Pramanik A (2015) Synthesis of biologically important, fluorescence active 5-hydroxy benzo[g]indoles through four-component domino condensations and their fluorescence “Turn-off” sensing of Fe(iii) ions. RSC Adv 5:52852–52865

    Article  CAS  Google Scholar 

  22. Wang W, Wei J, Liu H, Liu Q, Gao Y (2017) A novel colorimetric chemosensor based on quinoline for the sequential detection of Fe3+ and PPi in aqueous solution. Tetrahedron Lett 58:1025–1029

    Article  CAS  Google Scholar 

  23. Mukherjee S, Talukdar S (2016) A reversible pyrene-based turn-on luminescent chemosensor for selective detection of Fe3+ in aqueous environment with logic gate application. J Fluoresc 26:1021–1028

    Article  CAS  PubMed  Google Scholar 

  24. Ghosh K, Rathi S (2014) A novel probe for selective colorimetric sensing of Fe(ii) and Fe(iii) and specific fluorometric sensing of Fe(iii): DFT calculation and logic gate application. RSC Adv 4:48516–48521

    Article  CAS  Google Scholar 

  25. Goswami S, Aich K, Das AK, Manna A, Das S (2013) A naphthalimide–quinoline based probe for selective, fluorescence ratiometric sensing of trivalent ions. RSC Adv 3:2412

    Article  CAS  Google Scholar 

  26. Sen S, Sarkar S, Chattopadhyay B, Moirangthem A, Basu A, Dhara K, Chattopadhyay P (2012) A ratiometric fluorescent chemosensor for iron: discrimination of Fe2+ and Fe3+ and living cell application. Analyst 137:3335–3342

    Article  CAS  PubMed  Google Scholar 

  27. Ghosh K, Tarafdar D (2015) Piperazine-based new sensor: selective ratiometric sensing of Fe3+, logic gate construction and cell imaging. Supramol Chem 27:224–232

    Article  CAS  Google Scholar 

  28. Akula M, El-Khoury PJ, Nag A, Bhattacharya A (2014) Selective Zn2+ sensing using a modified bipyridine complex. RSC Adv 4:25605

    Article  CAS  Google Scholar 

  29. Akula M, Thigulla Y, Nag A, Bhattacharya A (2015) Selective detection of fluoride using fused quinoline systems: effect of pyrrole. RSC Adv 5:57231–57234

    Article  CAS  Google Scholar 

  30. Zhang XB, Cheng G, Zhang WJ, Shen GL, Yu RQ (2007) A fluorescent chemical sensor for Fe3+ based on blocking of intramolecular proton transfer of a quinazolinone derivative. Talanta 71:171–177

    Article  CAS  PubMed  Google Scholar 

  31. Wang P, Liu X, Fu J, Chang Y, Yang L, Xu K (2018) Synthesis and fluorescence spectral studies of novel quinolylbenzothiazole-based sensors for selective detection of Fe3+ion. Can J Chem 96:835–841

    Article  CAS  Google Scholar 

  32. Xue K, Wang P, Dong W, Luo X, Cheng P, Xu K (2018) Fluorescence Sensors for Fe3+ Ion with High Selectivity and Sensitivity and Bioimaging in Living Cells. Chem Select 3:11081

  33. Wang P, Fu J, Yao K, Chang Y, Xu K, Xu Y (2018) A novel quinoline-derived fluorescent “turn-on” probe for Cu2+ with highly selectivity and sensitivity and its application in cell imaging. Sensors Actuators B Chem 273:1070–1076

    Article  CAS  Google Scholar 

  34. Chang Y, Fu J, Yao K, Li B, Xu K, Pang X (2019) Novel fluorescent probes for sequential detection of Cu2+ and citrate anion and application in living cell imaging. Dyes Pigments 161:331–340

    Article  CAS  Google Scholar 

  35. Akula M, Padma Sridevi J, Yogeeswari P, Sriram D, Bhattacharya A (2014) New class of antitubercular compounds: synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines. Monatsh Chem 145:811–819

    Article  CAS  Google Scholar 

  36. Avirah RR, Jyothish K, Ramaiah D (2008) Infrared absorbing croconaine dyes: synthesis and metal ion binding properties. J Org Chem 73:274–279

    Article  CAS  PubMed  Google Scholar 

  37. Ding Y, Xie Y, Li X, Hill JP, Zhang W, Zhu W (2011) Selective and sensitive “turn-on” fluorescent Zn2+ sensors based on di- and tripyrrins with readily modulated emission wavelengths. Chem Commun 47:5431–5433

    Article  CAS  Google Scholar 

  38. Akula M, Yogeeswari P, Sriram D, Jha M, Bhattacharya A (2016) Synthesis and anti-tubercular activity of fused thieno-/furo-quinoline compounds. RSC Adv 6:46073–46080

    Article  CAS  Google Scholar 

  39. Tang J, Wang L, Mao D, Wang W, Zhang L, Wu S, Xie Y (2011) Ytterbium pentafluorobenzoate as a novel fluorous Lewis acid catalyst in the synthesis of 2,4-disubstituted quinolines. Tetrahedron 67:8465–8469

    Article  CAS  Google Scholar 

  40. Damera DP, Venuganti VVK, Nag A (2018) Deciphering the Role of Bilayer of a Niosome towards Controlling the Entrapment and Release of Dyes. Chem Select 3:3930

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Acknowledgements

T.U.K. thanks CSIR and BITS-Pilani for PhD fellowship. S.V.P. thanks DST- inspire (IF150605) scheme for providing senior research fellowship. A.N. thanks DST-SERB (SB/FT/CS-129/2013) for financial support. A.B. thanks Council for Scientific and Industrial Research, New Delhi for research grant. Authors gratefully acknowledge support from Department of Science and Technology, India for the FIST grant SR/FST/CSI-240/2012.

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  1. Department of Chemistry, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Hyderabad, 500078, India

    Togiti Uday Kumar, Shweta Pawar, Amit Nag & Anupam Bhattacharya

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  1. Togiti Uday Kumar
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  2. Shweta Pawar
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  3. Amit Nag
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Correspondence to Anupam Bhattacharya.

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Kumar, T.U., Pawar, S., Nag, A. et al. Selective Sensing of Iron by Pyrrolo[2,3-c]Quinolines. J Fluoresc 29, 271–277 (2019). https://doi.org/10.1007/s10895-018-02337-1

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  • DOI: https://doi.org/10.1007/s10895-018-02337-1

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