Novel emissive bio-inspired non-proteinogenic coumarin-Alanine amino acid: Fluorescent probe for polyfunctional systems

Amino Acids

Volumn 43, Issue 4, 2012, Pages 1779-1790

  Oliveira, Elisabete ^a,b   Capelo, José Luis ^a,c   Lima, João Carlos ^c   Lodeiro, Carlos ^a,c  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF TRÁS OS MONTES AND ALTO DOURO   (Portugal)

^c UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Acridine; Alanine; Coumarin; Lanthanide(III); Liposomes; Transition metals

Indexed keywords

ACRIDINE; ALANINE; ALUMINUM; CADMIUM; COUMARIN; COUMARIN ALANINE AMINO ACID; EUROPIUM; LANTHANIDE; LIPOSOME; TERBIUM; UNCLASSIFIED DRUG; ZINC ION;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOPHORE; ELECTROSPRAY MASS SPECTROMETRY; ENERGY TRANSFER; FLAME PHOTOMETRY; INFRARED SPECTROSCOPY; MELTING POINT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SPECTROSCOPY; TITRIMETRY; ULTRAVIOLET VISIBLE ABSORPTION SPECTROSCOPY;

ACRIDINES; ALANINE; ALUMINUM; AMINO ACIDS; CADMIUM; CATIONS; COUMARINS; DRUG DESIGN; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; LANTHANOID SERIES ELEMENTS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR PROBES; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; ZINC;

EID: 84867576051     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-012-1262-6     Document Type: Article

References (47)

1. 2+ co-ordination. Chem Phys Lett 353:63-68
2. Albert A(1966) In: The acridines: their preparation, physical, chemical, and biological properties and uses, 2nd edn. Edward Arnold, London
3. Albert A(1972) Medicinal chemical monograph. In: Ariens EJ (ed) Drug design, vol 3. Academic Press, New York
4. Amir M, Kumar H, Khan SA (2008) Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg Med Chem Lett 18:918-922
5. Bansal E, Srivastava VK, Kumar A(2001) Synthesis and anti-inflammatory activity of 1-Acetyl-5-substituted aryl-3-(beta-Aminonaphthyl)-2-pyrazolines and beta-(substituted aminoethyl) amidonaphthalenes. Eur J Med Chem 36:81-92
6. Bazzicalupi C, Bencini A, Berni E, Bianchi A, Giorgi C, Valtancoli B, Lodeiro C, Roque A, Pina F (2001) Coordination properties of Apolyamine cryptand with two different binding moieties. Acase of ApH-modulated antenna device based on Anew Eu(III) cryptate complex. Inorg Chem 40:6172-6179
7. 2+ based on Afluorescein platform: synthesis, properties and intracellular distribution. J Am Chem Soc 123:7831-7841
8. Cain BF, Atwell GJ (1974) The experimental antitumour properties of three congeners of the acridylmethanesulphonanilide (AMSA) series. Eur J Cancer 10:539-547
9. Chandler A, Read C (1961) Introduction to parasitology, 10th edn. Wiley, New York
10. Costa SPG, Oliveira E, Lodeiro C, Raposo MMM (2007) Synthesis, characterization and metal ion detection of novel fluoroionophores based on heterocyclic substituted alanines. Sensors 7:2096-2114
11. Costa SPG, Oliveira E, Lodeiro C, Raposo MMM (2008) Heteroaromatic alanine derivatives bearing (oligo)thiophene units: synthesis and photophysical properties. Tetrahedron Lett 49:5258-5261
12. Folliet N, Roiland C, Bégu S, Aubert A, Mineva T, Goursot A, Selvaraj K, Duma L, Tielens F, Mauri F, Laurent G, Bonhomme C, Gervais C, Babonneau F, Azaïs T (2011) Investigation of the interface in silica-encapsulated liposomes by combining solid state NMR and first principles calculations. J Am Chem Soc 133:16815-16827
13. Gans P, Sabatini A, Vacca A(1996) Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAQ suite of programs. Talanta 43:1739-1753
14. Hemmila I, Laitala V (2005) Progress in lanthanides as luminescent probes. J Fluoresc 15:529-542
15. Ko SK, Yang YK, Tae J, Shin I (2006) In vivo monitoring of mercury ions using Arhodamine-based molecular probe. J Am Chem Soc 128:14150-14155
16. 2+: complexation and fluorescence behavior of anthracene derivatives having diethylamine, N-methylpiperazine and N,N-bis(2-picolyl)amine units. J Mater Chem 15:2902-2907
17. 2+. Tetrahedron Lett 49:1261-1265
18. Li C, Wong W-T (2002) Luminescent terbium (III) complexes with pendant crown ethers responding to alkali metal ions and aromatic antennae in aqueous solution. Chem Commun 2034-2035
19. Lim NC, Bruchner C (2004) DPA-substituted coumarins as chemosensors for zinc(II): modulation of the chemosensory characteristics by variation of the position of the chelate on the coumarin. Chem Commun 9:1094-1095
20. Lodeiro C, Pina F (2009) Luminescent and chromogenic molecular probes based on polyamines and related compounds. Coord Chem Rev 253:1353-1383
21. Lodeiro C, Lima JC, Parola AJ, Seixas de Melo JS, Capelo JL, Covelo B, Tamayo A, Pedras B (2006) Intramolecular excimer formation and sensing behavior of new fluorimetric probes and their interactions with metal cations and barbituric acids. Sens Act B Chem 115:276-286
22. Lodeiro C, Capelo JL, Mejuto JC, Oliveira E, Santos HM, Pedras B, Nuñez C (2010) Light and colour as analytical detection tools: Ajourney into the periodic table using polyamines to bio-inspired systems as chemosensors. Chem Soc Rev 39:2948-2976
23. Lu C, Zu ZC, Cui JN, Zhang R, Qian XH (2007) Ratiometric and highly selective fluorescent sensor for cadmium under physiological pH range: Anew strategy to discriminate cadmium from zinc. J Org Chem 72:3554-3557
24. Marchi-Artzner V, Brienne MJ, Gulik-Krzywicki T, Dedieu JC, Lehn JM (2004) Selective complexation and transport of europium at the interface of vesicles. Chemistry 10:2342-2350
25. Martínez R, Chacón-García L (2005) The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work. Curr Med Chem 12:127-151
26. Montalti M, Credi A, Prodi L, Gandolfi MT (2006) Handbook of photochemistry, 3rd edn. Taylor and Francis, Boca Raton
27. Musa MA, Cooperwood JS, Khan MOF (2008) Areview of coumarin derivatives in pharmacotherapy of breast cancer. Curr Med Chem 15:2664-2679
28. Nolan EM, Jaworsky J, Racine ME, Sheng M, Lippard SJ (2006) Midrange affinity fluorescent Zn(II) sensors of the Zinpyr family: syntheses, characterization, and biological imaging applications. Inorg Chem 45:9748-9757
29. O'Kennedy R, Thornes RD (eds) (1997) Coumarins. Biology, applications and mode of action. Wiley, Chichester
30. Oliveira E, Genovese D, Juris R, Zaccheroni N, Capelo JL, Raposo MMM, Costa SPG, Prodi L, Lodeiro C (2011a) Bioinspired systems for metal-ion sensing: new emissive peptide probes based on benzo[d]oxazole derivatives and their gold and silica nanoparticles. Inorg Chem 50:8834-8849
31. Oliveira E, Nuñez C, Rodríguez-González B, Capelo JL, Lodeiro C (2011b) Novel small stable gold nanoparticles bearing fluorescent cysteine-coumarin probes as new metal-modulated chemosensors. Inorg Chem 50:8797-8807
32. 2+ detection. Inorg Chim Acta 380:22-30
33. Oliveira E, Santos HM, Capelo JL, Lodeiro C (2012b) New emissive dopamine derivatives as fluorescent chemosensors for metal ions: ACHEF effect for Al(III) interaction. Inorg Chim Acta 381:203-211
34. Pazos E, Vázquez O, Mascareñas JL, Vázquez ME (2009) Peptide-based fluorescent biosensors. Chem Soc Rev 38:3348-3359
35. Rajapakse HE, Reddy DR, Mohandessi S, Butlin NG, Miller LW (2009) Luminescent terbium protein labels for time-resolved microscopy and screening. Angew Chem Int Ed 48:4990-4992
36. Ray D, Bharadwaj PK (2008) Acoumarin-derived fluorescence probe selective for magnesium. Inorg Chem 47:2252-2254
37. Roy BD, AbulFazal MD, Arruda A, Mallik S, Campiglia AD (2000) Polymerized fluorescent liposomes incorporating lanthanide ions. Org Lett 2:3067-3070
38. Rubbo SD, Albert A, Maxwell MB (1942) The influence of chemical constitution on antiseptic activity I. Astudy of the mono-Amino-Acridines. J Exp Pathol 23:69-83
39. Silverstein RM, Bassler GC, Morrill TC (1980) Spectrometric identification of organic compounds, 4th edn. Wiley
40. 2+. Tetrahedron Lett 48:5966-5969
41. Steinkamp T, Karst U (2004) Detection strategies for bioassays based on luminescent lanthanide complexes and signal amplification. Anal Bioanal Chem 380:24-30
42. Striker G, Subramaniam V, Seidel CAM, Volkmer A(1999) Photochromicity and fluorescence lifetime of green fluorescent protein. J Phys Chem B 103:8612-8617
43. Tamayo A, Lodeiro C, Escriche L, Casabo J, Covelo B, González P (2005) New fluorescence PET systems based on N(2)S(2) pyridine-Anthracene- containing macrocyclic ligands. Spectrophotometric, spectrofluorometric, and metal ion binding studies. Inorg Chem 22:8105-8115
44. Thibon A, Pierre VC (2009) Principles of responsive lanthanide-based luminescent probes for cellular imaging. Anal Bioanal Chem 394:107-120
45. Trenor SR, Shultz AR, Love BJ, Long TE (2004) Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds. Chem Rev 104:3059-3077
46. 2+-induced blue shift of the pyrene excimer emission: Anew signal transduction mode of pyrene probes. Org Lett 6:889-892
47. Zhang WS, Tang B, Liu X, Liu YY, Xu KH, Ma JP, Tong LL, Yang GW (2009) Ahighly sensitive acidic pH fluorescent probe and its application to HepG2 cells. Analyst 134:367-371