Light-induced cleavage of model phenylalanine conjugates based on coumarins and quinolones

Amino Acids

Volumn 39, Issue 3, 2010, Pages 699-712

  Fonseca, Andrea S C ^a   Goncalves, M Sameiro T ^a   Costa, Susana P G ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Amino acids; Bioconjugates; Coumarin; Photocleavable protecting groups; Quinolone

Indexed keywords

AMINO ACID DERIVATIVE; CARBOXYLIC ACID; COUMARIN DERIVATIVE; ESTER; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; OXYGEN DERIVATIVE; PHENYLALANINE; QUINOLONE DERIVATIVE;

AMINO ACID TRANSPORT; ARTICLE; CONJUGATION; CONTROLLED STUDY; IRRADIATION; MOLECULAR MODEL; PHOTOLYSIS; PHOTOREACTIVATION; PHOTOSENSITIVITY; PHOTOSYNTHESIS; PRIORITY JOURNAL; SURFACE PROPERTY; CHEMICAL MODEL; CHEMISTRY; LIGHT; RADIATION RESPONSE;

COUMARINS; LIGHT; MODELS, CHEMICAL; PHENYLALANINE; PHOTOLYSIS; QUINOLONES;

EID: 77956619073     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0492-8     Document Type: Article

References (38)

1. Bochet CG (2002) Photolabile protecting groups and linkers. J Chem Soc Perkin Trans 1:125-142
2. Corrie JET, Furuta T, Givens R, Yousef AL, Goeldner M (2005) Dynamic studies in biology. In: Goeldner M, Givens R (eds). Wiley-VCH, Weinheim, pp 1-94
3. Fedoryak OD, Dore TM (2002) Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation. Org Lett 4:3419-3422
4. Fernandes MJG, Gonçalves MST, Costa SPG (2007) Photorelease of amino acid neurotransmitters from pyrenylmethyl ester conjugates. Tetrahedron 63:10133-10139
5. Fernandes MJG, Goncalves MST, Costa SPG (2008a) Comparative study of polyaromatic and polyheteroaromatic fluorescent photocleavable protecting groups. Tetrahedron 64:3032-3038
6. Fernandes MJG, Gonçalves MST, Costa SPG (2008b) Neurotransmitter amino acid-oxobenzo[f]benzopyran conjugates: synthesis and photorelease studies. Tetrahedron 64:11175-11179
7. Fonseca ASC, Goncalves MST, Costa SPG (2007) Photocleavage studies of fluorescent amino acid conjugates bearing different types of linkages. Tetrahedron 63:1353-1359
8. Furuta T, Wang SS-H, Dantzker JL, Dore TM, Bybee WJ, Callaway EM, Denk W, Tsien RY (1999) Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis. Proc Natl Acad Sci USA 96:1193-2000
9. Furuta T, Takeuchi H, Isozaki M, Takahashi Y, Kanehara M, Sugimoto M, Watanabe T, Noguchi K, Dore TM, Kurahashi T, Iwamura M, Tsien RY (2004) Bhc-cNMPs as either watersoluble or membrane-permeant photoreleasable cyclic nucleotides for both one-and two-photon excitation. ChemBioChem 5:1119-1128
10. Geissler D, Antonenko YN, Schmidt R, Keller S, Krylova OO, Wiesner B, Bendig J, Pohl P, Hagen V (2005) (Coumarin-4-yl)methyl esters as highly efficient, ultrafast phototriggers for protons and their application to acidifying membrane surfaces. Angew Chem Int Ed 44:1195-1198
11. Gilbert D, Funk K, Dekowski B, Lechler R, Keller S, Möhrlen F, Frings S, Hagen V (2007) Caged capsaicins: new tools for the examination of TRPV1 channels in somatosensory neurons. Chem Bio Chem 8:89-97
12. Gootz TD, Brighty KE (1998) The Quinolones. In: Andriole VT (ed), 2nd edn. Academic Press, San Diego, pp 29
13. Guillier F, Orain D, Bradley M (2000) Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem Rev 100:2091-2158
14. Hagen V, Frings S, Wiesner B, Helm S, Kaupp UB, Bendig J (2003) [7-(Dialkylamino)coumarin-4-yl]methyl-caged compounds as ultrafast and effective long-wavelength phototriggers of 8-bromo-substituted cyclic nucleotides. ChemBioChem 4:434-442
15. Hagen V, Dekowski B, Nache V, Schmidt R, Geissler D, Lorenz D, Eichhorst J, Keller S, Kaneko H, Benndorf K, Wiesner B (2005) Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one-and two-photon photolysis. Angew Chem Int Ed 44:7887-7891
16. Kessler M, Glatthar R, Giese B, Bochet CG (2003) Sequentially photocleavable protecting groups in solid-phase synthesis. Org Lett 5:1179-1181
17. Lin W, Lawrence DS (2002) A strategy for the construction of caged diols using a photolabile protecting group. J Org Chem 67:2723-2726
18. Lu M, Fedoryak OD, Moister BR, Dore TM (2003) Bhc-diol as a photolabile protecting group for aldehydes and ketones. Org Lett 5:2119-2122
19. Ma X, Zhou W, Brun R (2009) Synthesis, in vitro antitrypanosomal and antibacterial activity of phenoxy, phenylthio or benzyloxy substituted quinolones. Bioorg Med Chem Lett 19:986-989
20. Mayer G, Heckel A (2006) Biologically active molecules with a "light switch". Angew Chem Int Ed 45:4900-4921
21. Morris JV, Mahaney MA, Huber JR (1976) Fluorescence quantum yield determinations. 9, 10-Diphenylanthracene as a reference standard in different solvents. J Phys Chem 80:969-974
22. Noguchi M, Skwarczynski M, Prakash H, Hirota S, Kimura T, Hayashi Y, Kiso Y (2008) Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. Bioorg Med Chem 16:5389-5397
23. Pelliccioli AP, Wirz J (2002) Photoremovable protecting groups: reaction mechanisms and applications. Photochem Photobiol Sci 1:441-458
24. Piloto AM, Costa SPG, Goncalves MST (2005) A naphtho[2, 1-b]furan as a new fluorescent label: synthesis and spectral characterization. Tetrahedron Lett 46:4757-4760
25. Piloto AM, Fonseca ASC, Costa SPG, Goncalves MST (2006a) Carboxylic fused furans for amino acid fluorescent labeling. Tetrahedron 62:9258-9267
26. Piloto AM, Rovira D, Costa SPG, Gonçalves MST (2006b) Oxobenzo[f]benzopyrans as new fluorescent photolabile protecting groups for the carboxylic function. Tetrahedron 62:11955-11962
27. Reddy GV, Kanth SR, Maitraie D, Narsaiah B, Rao PS, Kishore KH, Murthy USN, Ravi B, Kumar BA, Parthasarathy T (2009) Design, synthesis, structure-activity relationship and antibacterial activity series of novel imidazo fused quinolone carboxamides. Eur J Med Chem 44:1570-1578
28. Senthilkumar P, Dinakaran M, Yogeeswari P, Sriram D, China A, Nagaraja V (2009) Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3- carboxylic acids. Eur J Med Chem 44:345-358
29. Shembekar VR, Chen Y, Carpenter BK, Hess GP (2007) Coumarincaged glycine that can be photolyzed within 3 μs by visible light. Biochemistry 46:5479-5484
30. Singh AK, Khade PK (2005) Anthracene-9-methanol-a novel fluorescent phototrigger for biomolecular caging. Tetrahedron Lett 46:5563-5566
31. Skwarczynski M, Noguchi M, Hirota S, Sohma Y, Kimura T, Hayashi Y, Kiso Y (2006) Development of first photoresponsive prodrug of paclitaxel. Bioorg Med Chem Lett 16:4492-4496
32. Suzuki AZ, Watanabe T, Kawamoto M, Nishiyama K, Yamashita H, Ishii M, Iwamura M, Furuta T (2003) Coumarin-4-ylmethox-ycarbonyls as phototriggers for alcohols and phenols. Org Lett 5:4867-4870
33. Takaoka K, Tatsu Y, Yumoto N, Nakajima T, Shimamoto K (2003) Synthesis and photoreactivity of caged blockers for glutamate transporters. Bioorg Med Chem Lett 13:965-970
34. Takaoka K, Tatsu Y, Yumoto N, Nakajima T, Shimamoto K (2004) Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker. Bioorg Med Chem 12:3687-3694
35. Tjoeng FS, Heavner GA (1981) Improved preparation of 4- (Bocaminoacyloxymethyl)-phenylacetic acids for use in peptidesynthesis on solid supports utilizing a protecting group removable by photolysis or reduction. Synthesis 897-899
36. Uray G, Niedereeiter KS, Belaj F, Fabian WMF (1999) Longwavelength- absorbing and-emitting carbostyrils with high fluorescence quantum yields. Helv Chim Acta 82:1408-1417
37. Yamaji M, Nozali K, Allonas X, Nakajima S, Tero-Kubota S, Marciniak B (2009) Photoinduced bond dissociation of 4-meth-ylcoumarin derivatives in solution studied by laser flash photolysis and DFT calculations. J Phys Chem A 113:5815-5822
38. Zhu Y, Pavlos CM, Toscano JP, Dore TM (2006) 8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope. J Am Chem Soc 128:4267-4276