[en] The reaction between the anaesthetic agent 2,6-diisopropylphenol (propofol, PPF) and singlet oxygen (1O2) has been investigated in aqueous solution by means of HPLC, GC, absorption spectroscopy and laser flash photolysis with infrared luminescence detection. The rate constants for the physical and chemical quenching of 1O2 by PPF (kPPF) are found to be 2.66 x 10(5) M(-1) s(-1) and approximately 3.2 x 10(6) M(-1) s(-1) in CD3OD and D2O-CD3OD (75:25 v/v), respectively. The reaction of propofol with singlet oxygen produced by light irradiation of Rose Bengal leads essentially to two reaction products, 2,6-diisopropyl-p-benzoquinone and 3,5,3',5'-tetraisopropyl-(4,4')-diphenoquinone that are unambiguously identified from comparison with authentic samples.
Kohnen, Stephan ; Université de Liège - ULiège > Département clinique des animaux de compagnie et des équidés > Anesthésiologie gén. et pathologie chirurg. des grds animaux
Brault, Daniel
Mouithys-Mickalad, Ange ; Université de Liège - ULiège > Centre de l'oxygène : Recherche et développement (C.O.R.D.)
Tfibel, Francis
Hans, Pol ; Université de Liège - ULiège > Département des sciences cliniques > Anesthésie et réanimation
Fontaine-Aupart, Marie-Pierre
Hoebeke, Maryse ; Université de Liège - ULiège > Département de physique > Spectroscopie biomédicale
Language :
English
Title :
Investigation of singlet oxygen reactivity towards propofol
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
H. M. Bryson, B. R. Fulton and D. Faulds, Propofol: an update of its use in anaesthesia and conscious sedation, Drugs, 1995, 50, 513-559.
P. G. Murphy, D. S. Myers, M. J. Davies, N. R. Webster and J. G. Jones, The antioxidant potential of propofol (2,6-diisopropylphenol), Br. J. Anaest., 1992, 68, 613-618.
O. Eriksson, P. Pollesello and L. N-E. Saris, Inhibition of lipid peroxidation in isolated rat liver mitochondria by the general anaesthetic propofol, Biochem. Pharmacol., 1992, 44(2), 391-393.
A. Mouithys-Mickalad, P. Hans, G. Deby-Dupont, M. Hoebeke, C. Deby and M. Lamy, Propofol reacts with peroxynitrite to form a phenoxyl radical: demonstration by electron spin resonance, Biochem. Biophys. Res. Commun., 1998, 249, 833-837.
M. Cudic and C. Ducrocq, Transformation of 2,6-diisopropylphenol by NO-derived nitrogen oxides, particulary peroxynitrite, Nitric Oxide: Biol. Chem., 2000, 4(2), 147-156.
S. L. Kohnen, A. A. Mouithys-Mickalad, G. P. Deby-Dupont, C. M. T. Deby, P. Hans, M. L. Lamy and A. F. Noels, Investigation of the reaction of peroxynitrite with propofol at acid pH: predominant production of oxidized, nitrated and halogenated derivatives, Nitric Oxide: Biol. Chem., in press.
B. A. Svingen, F. O. O'Nial and S. D. Aust, The role of superoxide and singulet oxygen in lipid peroxidation, Photochem. Photobiol., 1978, 28, 803-809.
M. C. Toufektsian, F. R. Boucher, S. Tanguy, S. Morel and J. G. de Leiris, Cardiac toxicity of singlet oxygen: implication in reperfusion injury, Antioxidants Redox Signalling, 2001, 3(1), 63-69.
C. S. Foote, T.-Y. Ching and G. G. Geller, Chemistry of singlet oxygen-XVIII. Rates of reaction and quenching of α-tocopherol and singlet oxygen, Photochem. Photobiol., 1974, 20, 511-513.
L. Aarts, R. van der Hee, I. Dekker, J. de Jong, H. Langemeijer and A. Bast, The widely used anesthetic agent propofol can replace α-tocopherol as an antioxidant, FEBS Lett, 1995, 357, 83-85.
E. Gandin, Y. Lion and A. Van de Vorst, Quantum yield of singlet oxygen production by xanthene derivatives, Photochem. Photobiol., 1983, 37(3), 271-278.
C. Vever-Bizet, O. Delgado and D. Brault, The purification of hematoporphyrin IX and its acetylated derivatives, J. Chromatogr., 1984, 283, 157-163.
E. Gandin, J. Piette and Y. Lion, Purification of halogenated fluorescein derivatives by gel chromatography, J. Chromatogr., 1982, 249, 393-398.
K. Omura, Rapid conversion of phenols to p-benzoquinones under acidic conditions with lead dioxide, Synthesis, 1998, 1145-1148.
A. Rieker, V. Rundel and H. Kessler, Die Unterscheidung ortho- und para-chinolider Strukturen, Z. Naturforsch., Teil B, 1969, 24, 547-562.
F. M. Menger and D. Carnahan, Comparison of phenolic couplings on KMnO4 and K2MnO4 surfaces, J. Org. Chem., 1985, 50, 3927-3928.
A. J. Fatiadi, Facile coupling of sterically hindered 2,6-dialkylphenols with periodic acid, Synthesis, 1973, 357-358.
G. Cardillo, R. Cricchio and L. Merlini, Reaction of ortho alkenyl-and alkylphenols with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) syntheses of 2,2-dialkylchromenes, Tetrahedron, 1971, 27, 1875-1883.
C. Tanielian and G. Heinrich, Effect of aggregation on the hematoporphyrin-sensitized production of singlet molecular oxygen, Photochem. Photobiol., 1995, 61, 131-135.
J. Davila and A. Harriman, Photoreactions of mocrocyclic dyes bound to human serum albumin, Photochem. Photobiol., 1990, 51 9-19.
P. Salomaa, L. Schaleger and F. A. Long, Solvent deuterium isotope effect on acid-base equilibria, J. Am. Chem. Soc., 1964, 86, 1-7.
J. C. Dearden and W. F. Forbes, Ligth absorption studies Part XIV. The ultraviolet absorption spectra of phenols., Can. J. Chem., 1959, 37, 1294-1304.
G. R. Fleming, A. W. E. Knight, J. M. Morris, R. J. S. Morrison and G. W. Robinson, Picosecond fluorescence studies of xanthene dyes, J. Am. Chem. Soc., 1977, 99, 4306-4311.
L. I. Grossweiner and E. F. Zwicker, Transient measurements of photochemical processes in dyes. I. The photosensitized oxidation of phenol by eosin and related dyes, J. Chem. Phys, 1961, 34(4), 1411-1417.
E. F. Zwicker and L. I. Grossweiner, Transient measurements of photochemical processes in dyes. II. The mechanism of the photosensitized oxidation of aqueous phenol by eosin, J. Phys. Chem., 1963, 67, 549-555.
M. Imamura and M. Koizumi, Irreversible photobleaching of the solution of fluorescent dyes. I. Kinetic studies on the primary process, Bull. Chem. Soc. Jpn., 1955, 28, 117-124.
M. Imamura, Irreversible photobleaching of the solution of fluorescent dyes. V. Photobleaching of erythrosin, Bull. Chem. Soc. Jpn., 1958, 31, 62-66.
M. Imamura, Irreversible photobleaching of the solution of fluorescent dyes. VI. Photobleaching of uranin in alkaline solutions, Bull. Chem. Soc. Jpn., 1958, 31, 962-969.
P. C. C. Lee and M. A. J. Rodgers, Laser flash photokinetic studies of Rose Bengal sensitized photodynamic interactions of nucleotides and DNA, Photochem. Photobiol., 1987, 45(1), 79-86.
N. Hasty, P. B. Merkel, P. Radlick and D. R. Kearns, Role of azide in singlet oxygen reactions: reaction of azide with singlet oxygen, Tetrahedron Lett., 1972, 1, 49-52.
M. A. J. Rodgers, Solvent-Induced deactivation of singlet oxygen: Additivity relationships in nonaromatic solvents, J. Am. Chem. Soc., 1983, 105(20), 6201-6205.
T. Matsuura, N. Yoshimura, A. Nishinaga and I. Saito, Photoinduced reactions. XXX. Hydrogen abstraction from a phenol by singlet oxygen, Tetrahedron Lett., 1969, 21, 1669-1671.
T. Matsuura, N. Yoshimura, A. Nishinaga and I. Saito, Photoinduced reactions-LVI participation of singlet oxygen in the hydrogen abstraction from a phenol in the photosensitized oxygenation, Tetrahedron, 1972, 28, 4933-4938.
M. J. Thomas and C. S. Foote, Chemistry of singlet oxygen-XXVI photooxygenation of phenols, Photochem. Photobiol., 1978, 27, 683-693.
M. Nowakowska and M. Kepczynski, Polymeric photosensitizers 2. Photosensitized oxidation of phenol in aqueous solution, J. Photochem. Photobiol. A: Chem., 1998, 116, 251-256.
R. Scurlock, M. Rougee and R. V. Bensasson, Redox properties of phenols, their relationships to singlet oxygen quenching and to their inhibitory effect on benzo(a)pyrene-induced neoplasia, Free Rad. Res. Comm., 1990, 8, 251-258.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.
