Saltar al contenido
Merck

Amino Acid-Porphyrin Conjugates: Synthesis and Study of their Photophysical and Metal Ion Recognition Properties.

Photochemistry and photobiology (2015-10-24)
Albish K Paul, Suneesh C Karunakaran, Joshy Joseph, Danaboyina Ramaiah
RESUMEN

Synthesis, photophysical and metal ion recognition properties of a series of amino acid-linked free-base and Zn-porphyrin derivatives (5-9) are reported. These porphyrin derivatives showed favorable photophysical properties including high molar extinction coefficients (>1 × 10(5) m(-1) cm(-1) for the Soret band), quantum yields of triplet excited states (63-94%) and singlet oxygen generation efficiencies (59-91%). Particularly, the Zn-porphyrin derivatives, 6 and 9 showed higher molar extinction coefficients, decreased fluorescence quantum yields, and higher triplet and singlet oxygen quantum yields compared to the corresponding free-base porphyrin derivatives. Further, the study of their interactions with various metal ions indicated that the proline-conjugated Zn-porphyrins (6 and 9) showed high selectivity toward Cu(2+) ions and signaled the recognition through changes in fluorescence intensity. Our results provide insights on the role of nature of amino acid and metallation in the design of the porphyrin systems for application as probes and sensitizers.

MATERIALES
Referencia del producto
Marca
Descripción del producto

Sigma-Aldrich
Ácido trifluoroacético, ReagentPlus®, 99%
Sigma-Aldrich
Ácido trifluoroacético, puriss. p.a., suitable for HPLC, ≥99.0% (GC)
Sigma-Aldrich
Tribromuro de boro solution, 1.0 M in methylene chloride
Sigma-Aldrich
L-Prolina, from non-animal source, meets EP, USP testing specifications, suitable for cell culture
Sigma-Aldrich
Pyrrole, reagent grade, 98%
Sigma-Aldrich
Ácido trifluoroacético, ≥99%, for protein sequencing
Sigma-Aldrich
p-Anisaldehyde, 98%
Sigma-Aldrich
HATU, 97%
Sigma-Aldrich
2,5-Dihydroxybenzoic acid, 98%
Sigma-Aldrich
Boron tribromide, ReagentPlus®, ≥99%
Sigma-Aldrich
2,3-Dichloro-5,6-dicyano-p-benzoquinone, 98%
Sigma-Aldrich
Boron tribromide, ≥99.99%
Supelco
2,5-Dihydroxybenzoic acid, matrix substance for MALDI-MS, >99.0% (HPLC)
Sigma-Aldrich
L-Prolina, BioUltra, ≥99.5% (NT)
SAFC
L-Prolina
Sigma-Aldrich
Boron tribromide, ReagentPlus®, 99.9%
Sigma-Aldrich
L-Prolina, ReagentPlus®, ≥99% (HPLC)
Sigma-Aldrich
L-Prolina, 99%, FCC, FG
Sigma-Aldrich
Pyrrole, ≥98%, FCC, FG
Sigma-Aldrich
HATU, ≥98.0% (CHN)
Sigma-Aldrich
Tribromuro de boro solution, 1.0 M in hexanes
Sigma-Aldrich
p-Anisaldehyde, ≥97.5%, FCC, FG
Sigma-Aldrich
Tribromuro de boro solution, 1.0 M in heptane
Sigma-Aldrich
meso-Tetraphenylporphyrin, BioReagent, suitable for fluorescence, ≥99.0% (HPLC)
Sigma-Aldrich
p-Anisaldehyde, natural, FG
Sigma-Aldrich
(S)-2-Amino-3-(1H-indol-3-yl)-propionic acid methyl ester, AldrichCPR