8-Hydroxyquinoline dansylates modified with PAMAM dendrimer as fluorescent Fe3+ Sensors

Molecules

Volumn 15, Issue 5, 2010, Pages 2962-2971

  Zhang, Qi ^a,b   Sha, Yaowu ^a   Wang, Jin Hui ^b  

^a Tsinghua University   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Dendrimers; Fe3+ ion; Flourescent sensors

Indexed keywords

8 QUINOLINOL; CHROMIUM; DANSYL ACID; DANSYL CHLORIDE; DENDRIMER; IRON; PAMAM STARBURST;

ARTICLE; CHEMISTRY; FLUORESCENCE;

CHROMIUM; DANSYL COMPOUNDS; DENDRIMERS; FLUORESCENCE; IRON; OXYQUINOLINE;

EID: 77952862002     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15052962     Document Type: Article

References (37)

1. Baars, M.W.P.L.; Meijer, E.W. Host-guest chemistry of dendritic molecules. Top. Curr. Chem. 2000, 210, 131-182.
2. Inoue, K. Functional dendrimers, hyperbranched and star polymers. Prog. Polym. Sci. 2000, 25, 453-571.
3. Newkome, G.R.; Shreiner, C.D. Poly(amidoamine), polypropylenimine, and related dendrimers and dendrons possessing different 1→2 branching motifs: An overview of the divergent procedures. Polymer 2008, 49, 1-173.
4. Esfand, R.; Tomalia, D.A. Poly(amidoamine) (PAMAM) dendrimers: From biomimicry to drug delivery and biomedical applications. DrugDiscov. Today 2001, 6, 427-436.
5. Liu, M.; Kono, K.; Frechet, J.M.J. Water-soluble dendritic unimolecular micelles: Their potential as drug delivery agents. J. Control. Release 2000, 65, 121-131.
6. Liu, M.; Fréchet, J.M.J. Preparation of Water-soluble dendritic unimolecular micelles as potential drug delivery agents. Polym. Mater. Sci. Eng. 1999, 80, 167-168.
7. Twyman, L.J.; Beezer, A.E.; Esfand, R.; Hardy, M.J.; Mitchell, J.C. The Synthesis of water soluble dendrimers, and their application as possible drug delivery systems. Tetrahedron Lett. 1999, 40, 1743-1746.
8. Pillai, O.; Panchagnula, R. Polymers in drug delivery. Curr. Opin. Chem. Biol. 2001, 5, 447-451.
9. Liu, M.; Frechet, J.M.J. Designing dendrimers for drug delivery. Pharm. Sci. Tech. Today 1999, 2, 393-401.
10. Smith, D.K.; Diederich, F. Functional Dendrimers: Unique Biological Mimics. Chem. Eur. J. 1998, 4, 1353-1361.
11. Bosman, A.W.; Janssen, H.M.; Meijer, E.W. About dendrimers: Structure, physical properties, and applications. Chem. Rev. 1999, 99, 1665-1688.
12. Froehling, P.E. Dendrimers and dyes-a review. Dyes Pigments 2001, 48, 187-195.
13. Weil, T.; Wiesler, U.M.; Herrmann, A.; Bauer, R.; Hofkens, J.; De Schryver, F.C.; Mullen, K. Polyphenylene dendrimers with different fluorescent chromophores asymmetrically distributed at the periphery. J. Am. Chem. Soc. 2001, 123, 8101-8108.
14. Gilat, S.L.; Adronov, A.; Fréchet, J.M.J. Modular Approach to the accelerated convergent growth of laser dye-labeled poly(aryl ether) dendrimers using a novel hypermonomer. J Org. Chem. 1999, 64, 7474-7484.
15. Gilat, S.L.; Adronov, A.; Fréchet, J.M.J. Light harvesting and energy transfer in novel convergently constructed dendrimers. Angew. Chem. Int. Ed. 1999, 38, 1422-1427.
16. Adronov, A.; Frechet, J.M.J. Light-harvesting dendrimers. Chem. Commun. 2000, 18, 1701-1710.
17. Jungle, D.M.; McGrath, D.V. Photoresponsive azobenzene-containing dendrimers with multiple discrete states. J. Am. Chem. Soc. 1999, 121, 4912-4913.
18. Fomie, S.; Rivera, E.; Fomina, L.; Ortiz, A.; Ogawa, T. Polymers from coumarines: 4. Design and synthesis of novel hyperbranched and comb-like coumarin-containing polymers. Polymer 1998, 39, 3551-3558.
19. Vogtle, F.; Gorka, M.; Hesse, R.; Ceroni, P.; Maestri, M.; Balzani, V. Photochemical and photophysical properties of poly(propylene amine) dendrimers with peripheral naphthalene and azobenzene groups. Photochem. Photobiol. Sci. 2002, 1, 45-51.
20. Balzani, V.; Ceroni, P.; Gestermann, S.; Kauffmann, C.; Gorka, M.; Vogtle, F. Dendrimers as fluorescent sensors with signal amplification. Chem. Commun. 2000, 10, 853-854.
21. Balzani, V.; Ceroni, P.; Gestermann, S.; Kauffmann, C.; Gorka, M.; Vogtle, F. Effect of protons and metal ions on the fluorescence properties of a polylysin dendrimer containing twenty four dansyl units. J. Chem. Soc. Dalton Trans. 2000, 21, 3765-3771.
22. Wang, J.; Jiang, M. Dendritic nucleic acid probes for DNA biosensors. J. Am. Chem. Soc. 1998, 120, 8281-8282.
23. Chang, A.C.; Gillespie, J.B.; Tabacco, M.B. Enhanced detection of live bacteria using a dendrimer thin film in an optical biosensor. Anal. Chem. 2001, 73, 467-470.
24. Shi D.X.; Sha Y.W.; Wang, F. Synthesis and Photophysical properties of poly(ester-amine) dendrimers with focal 4-amino-N-benzylphthalimide, as Sensitive media probes and switchable proton sensors. Macromolecules 2008, 41, 7478-7484.
25. Wang, F.; Peng, R.G.; Sha, Y.W. Selective dendritic fluorescent sensors for Zn(II). Molecules 2008, 13, 922-930.
26. Shen, L.; Li, F.Y.; Sha, Y.W. Synthesis of fluorescent dendritic 8-hydroxyquinoline ligands and investigation on their coordinated Zn(II) complexes. Tetrahedron Lett. 2004, 45, 3961-3964.
27. Sha, Y.W.; Shen, L.; Hong, X.Y. A divergent synthesis of new aliphatic poly(ester-amine) dendrimers bearing peripheral hydroxyl or acrylate groups. Tetrahedron Lett. 2002, 43, 9417-9419.
28. Hu, S.L.; She, N.F.; Yin, G.D.; Guo, H.Z.; Wu, A.X.; Yang, C.L. Synthesis, structural characterization, and fluorescent chemosensory properties of novel molecular clips based on diethoxycarbonyl glycoluril. Tetrahedron Lett. 2007, 48, 1591-1594.
29. Bricks, J.L.; Kovalchuk, A.; Trieflinger, C.; Nofz, M.; Buschel, M.; Tolmachev, A.I.; Daub, J.; Rurack, K. On the development of sensor molecules that display Fe(III)-amplified fluorescence. J. Am. Chem. Soc. 2005, 127, 13522-13529.
30. Ouchetto, H.; Dias, M.; Mornet, R.; Lesuisse, E.; Camadro, J.M. A new route to trihydroxamate- containing artificial siderophores and synthesis of a new fluorescent probe. Bioorg. Med. Chem. 2005, 13, 1799-1803.
31. Tumambac, G.E.; Rosencrance, C.M.; Wolf, C. Selective metal ion recognition using a fluorescent 1,8-diquinolylnaphthalene-derived sensor in aqueous solution. Tetrahedron 2004, 60, 11293-11297.
32. Ma, Y.; Luo, W.; Quinn, P.J.; Liu, Z.; Hider, R.C. Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors. J. Med. Chem. 2004, 47, 6349-6362.
33. Nudelman, R.; Ardon, O.; Hadar, Y.; Chen, Y.; Libman, J.; Shanzer, A. Modular fluorescent- labeled siderophore analogues. J. Med. Chem. 1998, 41, 1671-1678.
34. Weizman, H.; Ardon, O.; Mester, B.; Libman, J.; Dwir, O.; Hadar, Y.; Chen, Y.; Shanzer, A. Fluorescently-labeled ferrichrome analogs as probes for receptor-mediated, microbial iron uptake. J. Am. Chem. Soc. 1996, 118, 12368-12375.
35. Peng, R.; Wang, F.; Sha, Y.W. Synthesis of 5-dialkyl(aryl)aminomethyl-8- hydroxyquinoline dansylates as selective fluorescent sensors of Fe3+. Molecules 2007, 12, 1191-1201.
36. Fan, L.; Zhu, W.; Li, J.; Tian, H. Novel red-light emitting metal complex based on asymmetric perylene bisimide and 8-hydroxyquinoline dyads. Synth. Met. 2004, 145, 203-210.
37. Job, P. Studies on the formation of complex minerals in solution and on their stability. Ann. Chim. 1928, 9, 113-203