A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing-Manske hydrazinolysis and its applications in living cells

Dyes and Pigments

Volumn 103, Issue , 2014, Pages 9-20

  Ramakrishnam Raju, Mandapati V ^a   Chandra Prakash, Epperla ^b   Chang, Huan Cheng ^b   Lin, Hong Cheu ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b INSTITUTE OF ATOMIC AND MOLECULAR SCIENCES   (Taiwan)

Author keywords

Charge transfer; Fluorescent probe; Ing Manske hydrazinolysis; pH effects; Semi empirical calculations; Time resolved photoluminescence spectra

Indexed keywords

FLUORESCENT CHEMODOSIMETER; FLUORESCENT PROBES; HYDRAZINOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SEMI-EMPIRICAL CALCULATION; SIGNALLING MECHANISMS; TIME-RESOLVED PHOTOLUMINESCENCE; TIME-RESOLVED PHOTOLUMINESCENCE SPECTRUM;

CHARGE TRANSFER; MASS SPECTROMETRY; PH EFFECTS; PHOTOLUMINESCENCE; PROBES;

HYDRAZINE;

EID: 84890068208     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.11.015     Document Type: Article

References (58)

1. W. Rettig, B. Strehmel, S. Schrader, and H. Seifert Applied fluorescence in chemistry, biology and medicine 1999 Springer New York
2. J. Buffle, and G. Horvai In situ monitoring of aquatic systems; chemical analysis and speciation 2001 Wiley New York
3. D. Diamond, S. Coyle, S. Scarmagnani, and J. Hayes Wireless sensor networks and chemo-/biosensing Chem Rev 108 2008 652 679 (Pubitemid 351344452)
4. A. Shapira, Y.D. Livney, H.J. Broxterman, and Y.G. Assaraf Nanomedicine for targeted cancer therapy: towards the overcoming of drug resistance Drug Resist Updat 14 2011 150 163
5. H.W. Schiessl Kirk-Othmer encyclopedia of chemical technology 2000 John Wiley & Sons, Inc. 562
6. S. Garrod, M.E. Bollard, A.W. Nicholls, S.C. Connor, J. Connelly, and J.K. Nicholson Integrated metabonomic analysis of the multiorgan effects of hydrazine toxicity in the rat Chem Res Toxicol 18 2005 115 122 (Pubitemid 40256228)
7. S.S. Narayanan, and F. Scholz A comparative study of the electrocatalytic activities of some metal hexacyanoferrates for the oxidation of hydrazine Electroanalysis 11 1999 465 469
8. U. Ragnarsson Synthetic methodology for alkyl substituted hydrazines Chem Soc Rev 30 2001 205 213 (Pubitemid 33303574)
9. J.A.E. Hannum Recent developments in the technology of propellant hydrazines June 1982 Chemical Propulsion Information Agency CPTR 82-15
10. E.W. Schmidt Hydrazine and its derivatives: preparation, properties, applications 1984 Wiley New York
11. J. Wang Hydrazine detection using a tyrosinase-based inhibition biosensor Anal Chem 67 1995 3824 3827
12. S.D. Zelnick, D.R. Mattie, and P.C. Stepaniak Occupational exposure to hydrazines: treatment of acute central nervous system toxicity Aviat Space Environ Med 74 2003 1285 1291 (Pubitemid 37523137)
13. A. Serov, and C. Kwak Direct hydrazine fuel cells: a review Appl Catal B 98 2010 1 9
14. E.H. Vernot, J.D. MacEwen, R.H. Bruner, C.C. Haus, and E.R. Kinkead Long-term inhalation toxicity of hydrazine Fundam Appl Toxicol 5 1985 1050 1064 (Pubitemid 16186184)
15. Lyon International agency for research on cancer: re-evaluation of some organic chemicals, hydrazine, and hydrogen peroxide IARC monographs on the evaluation of carcinogenic risk of chemicals to humans vol. 71 1999 IARC 991 1013
16. S.M. Golabi, and H.R. Zare Electrocatalytic oxidation of hydrazine at a chlorogenic acid (CGA) modified glassy carbon electrode J Electroanal Chem 465 1999 168 176
17. W. Hou, and E. Wang Flow-injection amperometric detection of hydrazine by electrocatalytic oxidation at a prussian blue-film modified electrode Anal Chim Acta 257 1992 275 280
18. H. Xia, and H.L. Li Electrooxidation of hydrazine catalysed by 4-hydroxy-2,2,6,6-tetramethyl-piperidininyloxy (TEMPOL) J Electroanal Chem 430 1997 183 187 (Pubitemid 127378932)
19. I.G. Casella, M.R. Guascito, A.M. Salvi, and E. Desimoni Catalytic oxidation and flow detection of hydrazine compounds at a nifion/ruthenium(III) chemically modified electrode Anal Chim Acta 354 1997 333 341 (Pubitemid 28009263)
20. S.V. Guerra, C.R. Xavier, S. Nakagaki, and L.T. Kubota Electrochemical behavior of copper porphyrin synthesized into zeolite cavity: a sensor for hydrazine Electroanlaysis 10 1998 462 466 (Pubitemid 128437291)
21. X. Li, S. Zhang, and C. Sun Fabrication of covalently attached multilayer film electrode containing cobalt phthalocyanine and its electrocalalytic oxidation of hydrazine J Electroanal Chem 553 2003 139 145
22. M. Revenga-Parra, E. Lorenzo, and F. Pariente Synthesis and electrocalalytic activity towards oxidation of hydrazine a new family of hydroquinone salophen derivaives: application to the construction of hydrazine sensors Sens Actuators B Chem 107 2005 678 687 (Pubitemid 40655008)
23. B. Batchelor-McAuley, C.E. Banks, A.O. Simm, T.G.J. Jones, and R.G. Compton The electroanalytical detection of hydrazine: a comparision of the use of palladium nanoparticles supported on boron-doped diamond and palladium plated BDD microdisc array Analyst 131 2006 106 110 (Pubitemid 43117129)
24. J.A. Oh, J.H. Park, and H.S. Shin Sensitive determination of hydrazine in water by gas chromatography-mass spectrometry after derivatization of with ortho-phthalaldehyde Anal Chim Acta 769 2013 79 83
25. Z.K. He, B. Fuhrmann, and U. Spohn Coulometric microflow titrations with chemiluminescent and amperometric equivalence point detection: bromimetric titration of low concentration of hydrazine and ammonium Anal Chim Acta 409 2000 83 91 (Pubitemid 30114295)
26. Y.Y. Liu, I. Schmeltz, and D. Hoffmann Chemical studies on tobacco smoke: quantitative analysis of hydrazine in tobacco and cigarette smoke Anal Chem 46 1974 885 889
27. S.W. Thomas, and T.M. Swager Trace hydrazine detection with fluorescent conjugated polymers: a turn-on sensory mechanism Adv Mater 18 2006 1047 1050
28. M.G. Choi, J. Hwang, J.O. Moon, J. Sung, and S.K. Chang Hydrazine-selective chromogenic and fluorogenic probe based on levulinated coumarin Org Lett 13 2011 5260 5263
29. M.H. Lee, B. Yoon, J.S. Kim, and J.L. Sessler Naphthalimide trifluoroacetyl acetonate: a hydrazine- selective chemodosimeteric sensor Chem Sci 4 2013 4121 4126 10.1039/c3sc51813b
30. X. Chen, X. Tian, I. Shin, and J. Yoon Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species Chem Soc Rev 40 2011 4783 4804
31. J.F. Chang, Y. Zhou, J. Yoon, and J.S. Kim Recent progress in fluorescent and colorimetric for detection of precious metal ions (silver, gold and platinum ions) Chem Soc Rev 40 2011 3416 3429
32. 2+ Dyes Pigment 99 2013 323 328
33. J. Jiang, W. Liu, J. Cheng, L. Yang, H. Jiang, and D. Bai A sensitive colorimetric and ratiometric fluorescent probe for mercury species in aqueous solution and living cells Chem Commun 48 2012 8371 8373
34. P. Das, A.K. Mandal, N.B. Chandar, M. Baidya, H.B. Bhatt, and B. Ganguly New chemodosimeteric reagents as ratiometric probes for cysteine and homocysteine and possible detection in living cells and in blood plasma Chem Eur J 18 2012 15382 15393
35. L. Wang, Q. Zhou, B. Zhu, L. Yan, Z. Ma, and B. Du A colorimetric and fluorescent chemodosimeter for discriminative and simultaneous quantification of cysteine and homocysteine Dyes Pigment 95 2012 275 279
36. 2+ based on thiorhodamine 6G-amide and its application for biological imaging Dyes Pigment 98 2013 286 289
37. 4+ in aqueous media Dyes Pigment 96 2013 770 773
38. J. Du, M. Hu, J. Fan, and X. Peng Fluorescent chemodosimeters using "mild" chemical events for the detection of small anions and cations in biological and environment media Chem Soc Rev 41 2012 4511 4535
39. 3+ in aqueous media Chem Commun 48 2012 1039 1041
40. M.G. Choi, J.K. Moon, J. Bae, W. Lee, and S.K. Chang Dual signalling of hydrazine by selective deprotection of chlorofluorescein and resorufin acetates Org Biomol Chem 11 2013 2961 2965
41. Y. Xu, B. Li, W. Li, J. Zhao, S. Sun, and Y. Pang "ICT-not- quenching" near infrared ratiometric fluorescent detection of picric acid in aqueous media Chem Commun 49 2013 4764 4766
42. K. Li, H.R. Xu, K.K. Yu, J.T. Hou, and X.Q. Yu A coumarin based chromogenic and ratiometric probe for hydrazine Anal Methods 5 2013 2653 2656
43. X. Chen, Y. Xiang, Z. Li, and A. Tong Sensitive and selective fluorescence determination of trace hydrazine in aqueous solution utilizing 5-chlorosalcicylalehyde Anal Chim Acta 625 2008 41 46
44. J. Fan, W. Sun, M. Hu, J. Cao, G. Cheng, and H. Dong An ICT-based ratiometric probe for hydrazine and its application in live cells Chem Commun 48 2012 8117 8119
45. C. Hu, W. Sun, J. Cao, P. Gao, J. Fan, and F. Song A ratiometric near-infrared fluorescent probe for hydrazine and its in vivo applications Org Lett 15 2013 4022 4025
46. M.N. Khan Kinetic evidence for the occurrence of a stepwise mechanism in hydrozinolysis of phthalimide J Org Chem 60 1995 4536 4541
47. M.R. Duke, E.B. Veale, P.E. Kruger, and T. Gunnlaugsson Colorimetric and fluorescent anion sensors: an overview of in the recent developments in the use of 1,8-naphthalimide-based chemosensors Chem Soc Rev 39 2010 3936 3953
48. N.I. Georgiev, V.B. Bojinov, and P.S. Nikolov The design, synthesis and photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET and ICT Dyes Pigment 88 2011 350 357
49. M. Wang, Z. Xu, X. Wang, and J. Cui A fluorescent and colorimetric chemosensor for nitric oxide based on 1,8-naphthalimide Dyes Pigment 96 2013 333 337
50. J. March Advanced organic chemistry: reactions, mechanisms and structures 2nd ed. 1977 McGraw-Hill Kogakusha, Ltd. Tokyo 388
51. W.A. Bolhoter, and J.C. Sheehan An improved procedure for the condensation of potassium phthalimide with organic halides J Am Chem Soc 72 1950 2786 2788
52. M.S. Gibson, and R.W. Bradshaw The Gabriel synthesis of primary amines Angew Chem Int Ed 7 1968 919 930
53. Frisch MJ et al. Gaussian, Inc.: Wallingford CT; 2009.
54. H. Tian, J. Gan, K. Chen, J. He, Q.L. Song, and X.Y. Hou Positive and negative fluorescent imaging induced by naphthalimide polymers J Mater Chem 12 2002 1262 1267
55. M. Shortreed, R. Kopelman, M. Kuhn, and B. Hoyland Fluorescent fiber-optic calcium sensor for physiological measurements Anal Chem 68 1996 1414 1418
56. A. Umar, M.M. Rahman, S.H. Kim, and Y.B. Hahn Zinc oxide nanonail based chemical sensor for hydrazine detection Chem Commun 2008 166 168 (Pubitemid 350294088)
57. H.R. Ing, and R.H.F. Manske A modification of the Gabriel synthesis of amines J Chem Soc 1926 2348 2351
58. A. Ariffin, M.N. Khan, L.C. Lan, F.Y. May, and C.S. Yun Suggested improved method for the Ing-Manske and related reactions for the second step of Gabriel synthesis of primary amines Synth Commun 34 2004 4439 4445 (Pubitemid 40070222)