TY - JOUR
T1 - Non-toxic fluorescent alanine-fluorescein probe with green emission for dual colorimetric/fluorimetric sensing
AU - Oliveira, Elisabete
AU - Lorenzo, Julia
AU - Cid, Antonio
AU - Capelo, José Luis
AU - Lodeiro, Carlos
N1 - Authors thank Xunta de Galicia (Biomedicine) for the research Grant 09CSA043383PR, and Scientific PROTEOMASS Association (Portugal) for financial support. E.O. and A.C. thanks to MEC-FCT (Portugal) for their post-doctoral Grants SRFH/BPD/72557/2010 and SFRH/BPD/78849/2011 respectively. J.L. thanks to Ministerio de Ciencia e Innovacion (MICINN-Spain), for Grant BIO2010-22321-C02.
PY - 2013/1/1
Y1 - 2013/1/1
N2 - Two new fluorescent bio-inspired dyes 1 and 2 containing a fluorescein unit linked to a protected with a Boc group (N-tert-butyloxycarbonyl), and unprotected alanine residue were synthesized and characterized. The acid-base behavior was studied in water/ethanol (60/40) and at pH = 8 a strong emission fluorescence, followed by a color change from colorless to yellow was observed. Photophysical studies in water HEPES buffered solution toward alkaline, alkaline earth, transition, and post- transition metal ions were performed. Compounds 1 and 2 revealed to be very sensitive to Hg2+ with colorimetric changes from yellow to pink in the presence of HEPES buffer. Moreover, compound 1 show a color change from yellow to orange in the presence of the neurotransmitter molecule dopamine. Compound 2 also reveals to be sensitive to Cu2+ and Ni2+ , being able to detected and quantified in HEPES buffer ca. 0.37 ppm and ca. 1.50 ppm of Cu2+ , respectively. Very small silver nanoparticles coated with compound 2 of ca. 3.68 ± 0.93 nm were successfully synthesized and characterized. Toxicological studies with both compounds were also carried out.
AB - Two new fluorescent bio-inspired dyes 1 and 2 containing a fluorescein unit linked to a protected with a Boc group (N-tert-butyloxycarbonyl), and unprotected alanine residue were synthesized and characterized. The acid-base behavior was studied in water/ethanol (60/40) and at pH = 8 a strong emission fluorescence, followed by a color change from colorless to yellow was observed. Photophysical studies in water HEPES buffered solution toward alkaline, alkaline earth, transition, and post- transition metal ions were performed. Compounds 1 and 2 revealed to be very sensitive to Hg2+ with colorimetric changes from yellow to pink in the presence of HEPES buffer. Moreover, compound 1 show a color change from yellow to orange in the presence of the neurotransmitter molecule dopamine. Compound 2 also reveals to be sensitive to Cu2+ and Ni2+ , being able to detected and quantified in HEPES buffer ca. 0.37 ppm and ca. 1.50 ppm of Cu2+ , respectively. Very small silver nanoparticles coated with compound 2 of ca. 3.68 ± 0.93 nm were successfully synthesized and characterized. Toxicological studies with both compounds were also carried out.
KW - Alanine
KW - Dopamine
KW - Fluorescein
KW - Fluorescent chemosensors
KW - Toxicity studies
UR - http://www.scopus.com/inward/record.url?scp=84880985081&partnerID=8YFLogxK
U2 - 10.1016/j.jphotochem.2013.06.015
DO - 10.1016/j.jphotochem.2013.06.015
M3 - Article
AN - SCOPUS:84880985081
SN - 1010-6030
VL - 269
SP - 17
EP - 26
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
ER -