66067-43-4Relevant academic research and scientific papers
Water concentration dependent photochemistry of ketoprofen in aqueous solutions
Li, Ming-De,Du, Yong,Chuang, Yung Ping,Xue, Jiadan,Phillips, David Lee
, p. 4800 - 4808 (2010)
Ketoprofen is an important photosensitive drug molecule that has received much attention for the study of its photochemistry in different solvents. In this paper, nanosecond time-resolved resonance Raman spectroscopy was utilized to investigate the photochemistry of ketoprofen in aqueous solutions with varying water concentrations. The rate constants and reaction mechanism of ketoprofen are strongly dependent on the concentration of the solvent. In neat acetonitrile and solvents with low concentrations of water (like water-acetonitrile ≤ 1:1, v/v), ketoprofen exhibits mostly benzophenone-like photochemistry to generate a triplet state which in turn produces a ketyl radical-like species by a hydrogen abstraction reaction. However, in solvents with very high concentrations of water (such as water-acetonitrile ≥ 9:1, v/v), the triplet state ketoprofen is observed first and then undergoes a prompt decarboxylation process to form a triplet protonated biradical carbanion species. For solvents with moderate higher water concentrations (such as between 50% and 90% water by volume), the hydrogen abstraction and decarboxylation processes are two competitive pathways with different rate constants. The triplet state of ketoprofen will simultaneously produce a ketyl radical species and a triplet protonated biradical carbanion species with the amount of each species dependent on the water concentration. the Owner Societies.
Local Light-Controlled Generation of Calcium Carbonate and Barium Carbonate Biomorphs via Photochemical Stimulation
Menichetti, Arianna,Mavridi-Printezi, Alexandra,Falini, Giuseppe,Besirske, Patricia,García-Ruiz, Juan Manuel,C?lfen, Helmut,Montalti, Marco
, p. 12521 - 12525 (2021)
Photochemical activation is proposed as a general method for controlling the crystallization of sparingly soluble carbonates in space and time. The photogeneration of carbonate in an alkaline environment is achieved upon photo-decarboxylation of an organic precursor by using a conventional 365 nm UV LED. Local irradiation was conducted focusing the LED light on a 300 μm radius spot on a closed glass crystallization cell. The precursor solution was optimized to avoid the precipitation of the photoreaction organic byproducts and prevent photo-induced pH changes to achieve the formation of calcium carbonate only in the corresponding irradiated area. The crystallization was monitored in real-time by time-lapse imaging. The method is also shown to work in gels. Similarly, it was also shown to photo-activate locally the formation of barium carbonate biomorphs. In the last case, the morphology of these biomimetic structures was tuned by changing the irradiation intensity.
Increasing the life expectancy of carbanions by zeolite inclusion
Chretien, Michelle N.,Cosa, Gonzalo,Garcia, Hermenegildo,Scaiano
, p. 2154 - 2155 (2002)
Carbanions have been detected for the first time in zeolite cavities where their lifetime is more than ten times longer than in solution; included carbanions show Grignard-like behaviour.
Influence of solvent polarity and base concentration on the photochemistry of ketoprofen: Independent singlet and triplet pathways
Cosa, Gonzalo,Martinez, Lydia J.,Scaiano
, p. 3533 - 3537 (1999)
The photochemistry of ketoprofen in aqueous solutions is strongly influenced by its acid-base chemistry. While the acid form of ketoprofen behaves as a typical benzophenone chromophore, the ketoprofen carboxylate undergoes efficient photodecarboxylation i
Photochemical reaction of 2-(3-benzoylphenyl)propionic acid (ketoprofen) with basic amino acids and dipeptides
Suzuki, Tadashi,Shinoda, Mio,Osanai, Yohei,Isozaki, Tasuku
, p. 9662 - 9668 (2013)
Photoreaction of 2-(3-benzoylphenyl)propionic acid (ketoprofen, KP) with basic amino acids (histidine, lysine, and arginine) and dipeptides (carnosine and anserine) including a histidine moiety in phosphate buffer solution (pH 7.4) has been investigated w
Water- and acid-mediated excited-state intramolecular proton transfer and decarboxylation reactions of ketoprofen in water-rich and acidic aqueous solutions
Li, Ming-De,Yeung, Chi Shun,Guan, Xiangguo,Ma, Jiani,Li, Wen,Ma, Chensheng,Phillips, David Lee
, p. 10935 - 10950 (2011)
We present an investigation of the decarboxylation reaction of ketoprofen (KP) induced by triplet excited-state intramolecular proton transfer in water-rich and acidic solutions. Nanosecond time-resolved resonance Raman spectroscopy results show that the
A remarkably long-lived benzyl carbanion
Laferriere, Marie,Sanrame, Carlos N.,Scaiano
, p. 873 - 875 (2004)
(Equation presented) The photochemistry of ketoprofen, a widely used nonsteroidal antiinflammatory drug (NSAID) has been the subject of several studies as a result of its known phototoxicity. Photolysis of ketoprofen leads to 3-ethylbenzophenone, a proces
Diastereoselectivity and site dependency in the photochemistry of ketoprofen in the bovine serum albumin matrix
Monti, Sandra,Manet, Ilse,Manoli, Francesco,Morrone, Raffaele,Nicolosi, Giovanni,Sortino, Salvatore
, p. 13 - 19 (2006)
The photodegradation of the S(+)- and R(-)-ketoprofen (KP) enantiomers in the bovine serum albumin matrix was studied by steady-state photolysis with the use of λirr 320 nm and transient absorption spectroscopy with λexc = 355 nm, at 1/1 and 2/1 KP/BSA molar ratios. R(-)-KP was found to be more labile than S(+). Triplet ketoprofen species were evidenced with lifetimes of 400 ns for S(+) and 600 ns for R(-)-KP. Further longer-lived transients with lifetimes of 2.6 and 6.0 μs for S(+) and R(-), respectively, were detected. On the basis of the binding constants of the drug enantiomers to the two main binding sites of the protein, obtained from circular dichroism experiments, the individual disappearance quantum yields of the 1:1 and 2:1 diastereomeric KP:BSA complexes could be estimated. The photoreactivity in the BSA matrix was rationalized on the basis of diastereoselective photodecarboxylation in the two main protein sites.
Triplet Photoreactivity of the Diaryl Ketone Tiaprofenic Acid and Its Decarboxylated Photoproduct. Photobiological Implications
Encinas, Susana,Miranda, Miguel A.,Marconi, Giancarlo,Monti, Sandra
, p. 420 - 425 (1998)
The 2-benzoylthiophene chromophore of the photosensitizing drug tiaprofenic acid and of its decarboxylated derivative is characterized by a unusually high energy gap between the T1 (π,π*) and T2 (n,π*) excited states, which makes thi
Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen): Part 1. A picosecond and nanosecond time resolved study in aqueous solution
Monti, Sandra,Sortino, Salvatore,De Guidi, Guido,Marconi, Giancarlo
, p. 2269 - 2275 (1997)
The photochemistry of ketoprofen (KPF), 2-(3-benzoylphenyl)propionic acid, has been studied in aqueous solutions by time resolved (picosecond and nanosecond) spectroscopic techniques. Excited-state calculations were performed. The overall reactivity of th
