Evaluation of photoluminescence properties of some poly(ethylene glycol) - Supported coumarin derivatives

Molecules

Volumn 14, Issue 3, 2009, Pages 1044-1055

  Tocco, Graziella ^a   Carbonaro, Carlo Maria ^a   Meli, Gabriele ^a   Podda, Gianni ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Coumarins; PEG conjugation.; Photoluminescence; Poly(ethylene glycol)

Indexed keywords

COUMARIN DERIVATIVE; MACROGOL DERIVATIVE;

ARTICLE; CHEMISTRY; LUMINESCENCE; RADIATION EXPOSURE; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET RADIATION;

COUMARINS; LUMINESCENCE; POLYETHYLENE GLYCOLS; STRUCTURE-ACTIVITY RELATIONSHIP; ULTRAVIOLET RAYS;

EID: 63449127661     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14031044     Document Type: Article

References (40)

1. Marshall, M.E.; Kervin, K.; Benefield, C.; Umerani, A.; Albainy-Jenei, S.; Zhao, Q.; Khazaeli, M.B. Growth-inhibitory Effects of Coumarin (1,2-benzopyrone) and 7-Hydroxycoumarin on Human Malignant Cell Lines in Vitro. J. Cancer Res. Clin. Oncol. 1994, 120, 3-10;
2. Tanaka, T.; Kumamoto, T.; Ishikawa T. Enantioselective Total Synthesis of Anti HIV-1 Active (+)-Calanolide A through a Quinine-catalyzed Asymmetric Intramolecular Oxo-Michael Addition. Tetrahedron Lett. 2000, 41, 10229-10232.
3. Erk, C.; Gocmen, A.; Bulut, M. The Synthesis of Novel Macrocycles, Part V. The Coumarin Crown Ethers and Cation Binding with Fluorescence Spectra. Supramol. Chem. 1999, 11, 49-56.
4. Trenor, S.R.; Shultz, A.R.; Love, B.J.; Long, T.E. Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds. Chem. Rev. 2004, 104, 3059-3078.
5. Trenor, S.R.; Love, B.J.; Long, T.E. Photoreversible Chain Extension of Poly(ethylene glycol). Macromol. Chem. Phys. 2004, 205, 715-723.
6. th Congress International de Chimie Industrielle, 1967, 3, 373.
7. Serin, J.; Schultze, X.; Adronov, A.; Frechet, J.M.J. Synthesis and Study of the Absorption and Luminescence Properties of Polymers Containing Ru(BpyMe2)32+ Chromophores and Coumarin Laser Dyes.Macromolecules 2002, 35, 5396-5404.
8. Mal, N.K.; Fujiwara, M.; Tanaka, Y. Photocontrolled Reversible Release of Guest Molecules from Coumarin-modified Mesoporous Silica. Nature 2003, 421, 350-353.
9. Suratwala, T.; Gardlund, Z.; Davidson, K.; Uhlmann, D.R.; Watson, J.; Peyghambarian, N. Silylated Coumarin Dyes in Sol-Gel Hosts. 1. Structure and Environmental Factors on Fluorescent Properties. Chem. Mater. 1998, 10, 190-198.
10. Barberis, V.P.; Mikroyannidis, J.A.; Cimrova, V. Coumarin-containing Poly(fluorinediylvinylene) s: Synthesis, Photophysics and Electroluminescence. J. Polym. Sci.: Part A Polym. Chem. 2006, 44, 5750-5762.
11. Zarebska, Z.; Waszkowska E.; Caffieri, S.; Dall'Acqua, F. PUVA (psoralen+UVA) Photochemotherapy: Processes Triggered in the Cells. Il Farmaco 2000, 55, 515-520.
12. Yu, D.L.; Suzuki, M.; Xie, L.; Morris-Natschke, S.L.; Lee, K.H. Recent Progress in the Development of Coumarin Derivatives as Potent anti-HIV Agents. Med. Res. Rev. 2003, 23, 322-345.
13. Tocco, G.; Begala, M.; Delogu, G.; Meli, G.; Picciau, C.; Podda, G. Soluble Polymer-supported Synthesis of 4-Methyl coumarin on Modified Poly(ethylene glycol)s Synlett. 2005, 8, 1296-1300.
14. Tocco, G.; Fais, A.; Meli, G.; Begala, M.; Podda, G.; Fadda, M.B.; Corda, M.; Attanasi, O.A.; Filippone, P.; Berretta, S. PEG-immobilization of Cardol and Soluble Polymer-Supported Synthesis of Some Cardol-coumarin Derivatives: Preliminary Evaluation of Their Inhibitory Activity on Mushroom Tyrosinase. Bioorg. Med. Chem. Lett. 2009, 19, 36-39.
15. Dickerson, T.J.; Reed, N.N.; Janda, K.D. Soluble polymers as Scaffolds for Recoverable Catalysts and Reagents. Chem. Rev. 2002, 102, 3325-3243.
16. Greenwald, R.B. PEG drugs: an overview. J. Control. Release 2001, 74, 159-171.
17. Dall'Acqua, F.; Vedaldi, D. CRC Handbook of Organic Photochemistry and Photobiology; CRC Press: Boca Raton, FL, USA, 1995.
18. Dalla Via, L.; Marciani Magno, S. Photochemotherapy in the Treatment of Cancer. Curr. Med. Chem. 2001, 8, 1405-1418.
19. Wolfbeis, O.S. Optical Sensors; Springer-Verlag: Heidelberg, Germany, 2004.
20. Mohr, G.J. Chromo- and Fluororeactands: Indicators for Detection of Neutral Analytes by Using Reversible Covalent-Bond Chemistry. Chem. Eur. J. 2004, 10, 1082-1090.
21. Pu, L. Fluorescence of Organic Molecules in Chiral Recognition. Chem. Rev. 2004, 104, 1687-1716.
22. Martinez-Manez, R.; Sancenon, F. Fluorogenic and Chromogenic Chemosensors and Reagents for Anions. Chem. Rev. 2003, 103, 4419-4476.
23. Wiskur, S.L.; Ait-Haddou, H.; Anslyn, E. V.; Lavigne, J. Teaching Old Indicators new Tricks. J. Acc. Chem. Res. 2001, 34, 963-972.
24. Desvergne, J.-P.; Czarnik, A.W. Chemosensors of Ion and Molecular Recognition; Kluwer Academic Press: Dordrecht, the Netherlands, 1997.
25. de Silva, A.P.H.; Gunaratne, Q.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515-1566.
26. Czarnik, A.W. Fluorescent Chemosensors for Ion and Molecule Recognition Ed. ACS Symposium Series No. 538; American Chemical Society: Washington DC, USA, 1993.
27. Valeur, B. Topics in Fluorescence Spectroscopy, Vol. 4: Probe Design and Chemical Sensing; Lakowicz, J.R. Ed.; Plenum Press: New York, USA, 1994.
28. Annunziata, R.; Benaglia, M; Cinquini, M.; Cozzi, F.; Tocco, G. A Poly(ethylene glycol)- Supported Quaternary Ammonium Salt: an Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst. Org. Lett. 2000, 2, 1737-1739.
29. Reger, T.S.; Janda, K.D. Polymer-Supported (Salen)Mn Catalysts for Asymmetric Epoxidation: a Comparison between Soluble and Insoluble Matrices. J. Am. Chem. Soc. 2000, 122, 6929-6934.
30. Benaglia, M.; Danelli, T.; Pozzi, G. Synthesis of Poly(ethylene glycol)-supported Manganese Porphyrins: Efficient, Recoverable and Recyclable Catalysts for Epoxidation of Alkenes. Org. Biomol. Chem. 2003, 1, 454-456.
31. Anyanuwu, U.K.; Venkataraman, D. Effect of Spacers on the Activity of Soluble Polymer Supported Catalysts for the Asymmetric Addition of Diethylzinc to Aldehydes. Tetrahedron Lett. 2003, 44, 6445-6448.
32. Schäfer, F.P. Topics in Applied Physics, vol. 1, Dye Lasers, Schäfer, F.P., Ed.; Springer-Verlag: Berlin, Germany, 1990.
33. Jones, G. II; Jackson, W.R.; Choi, C. Solvent Effects on Emission Yield and Lifetime for Coumarin Laser Dyes. Requirements for a Rotatory Decay Mechanism. J. Phys. Chem. 1985, 89, 294-300.
34. Wheelock, C. The Fluorescence of Some Coumarins. Am. Chem. Soc. 1959, 81, 1348-1352.
35. Krasovitskii, B.M.; Bolotin, B.M. Organic Luminescent Materials; VCH: Weinheim, Germany, 1988.
36. Takadate, A.; Masuda, T.; Murata, C.; Shibuya, M.; Isobe, A. Structural Features for Fluorescing Present in Methoxycoumarin Derivatives. Chem Pharm. Bull. 2000, 48, 256-260.
37. Veronese, F.M.; Morpurgo, M. Bioconjugation in Pharmaceutical Chemistry. Il Farmaco 1999, 54, 497-516.
38. Harris, J.M. Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications; Harris, J.M., Ed.; Plenum Press, New York, USA, 1992.
39. Zhao, X.Y.; Metz, W.A.; Sieber, F.; Janda, K.D. Expanding on the purification methodology of polyethylene glycol (PEG) bound molecules: The synthesis of 3,5-pyrazolidinediones. Tetrahedron Lett. 1998, 39, 8433-8436.
40. Del Monte, F.; Levy, D. Formation of Fluorescent Rhodamine B J-Dimers in Gel-Glasses Induced by the Adsorption Geometry on the Silica Surface. J. Phys. Chem. B 1998, 102, 8036-8041.