[en] The photochemistry of the anaesthetic agent propofol (PPF) was investigated in three different solvents of quite different polarity (cyclohexane, methanol and phosphate buffer pH 7) by means of nanosecond laser flash photolysis and absorption spectroscopy. GC-MS spectrometry measurements of PPF in cyclohexane have revealed the formation of two major products upon low intensity UV continuous irradiation of PPF in aerated solution: the diphenol derivative of PPF and 2,6-diisopropyl-p-benzoquinone (PPFQ). Only the diphenol compound was obtained in anaerobic solution. PPF phenoxyl radical (PPF ) generation has been assigned as the original step leading to the formation of both the diphenol compound and PPFQ in cyclohexane as revealed by laser flash photolysis at 266 nm and by electron paramagnetic resonance spectroscopy as well. Investigation of PPF by nanosecond flash photolysis at 266 nm in the other solvents revealed the occurrence of different photochemical processes depending on the nature and the polarity of the solvent. A reaction scheme is proposed in order to discuss the mechanism of reaction of PPF in all media.
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 D. Faulds Drugs 1995 50 513.
L. Aarts R. Van, de Hee I. Dekker J. De, Jong H. Langemeijer A. Bast FEBS Lett. 1995 357 83.
O. Eriksson P. Pollesello N.-E. Leo, Saris Biochem. Pharmacol. 1992 44 391.
P. G. Murphy J. R. Bennet D. S. Myers M. J. Davies J. G. Jones Eur. J. Anaesthesiol. 1993 10 261.
P. G. Murphy D. S. Myers M. J. Davies N. R. Webster J. G. Jones Br. J. Anaesth. 1992 68 613.
S. Kohnen A. Mouithys-Mickalad G. Deby-Dupont C. Deby P. Hans M. Lamy A. Noels Nitric Oxide 2003 8 170.
A. Mouithys-Mickalad P. Hans G. Deby-Dupont M. Hoebeke C. Deby M. Lamy Biochem. Biophys. Res. Commun. 1998 249 833.
K. Briviba L.-O. Klotz H. Sies Biol. Chem. 1997 378 1259.
M. J. Davies Biochem. Biophys. Res. Commun. 2003 305 761.
B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press, Oxford and New York, 2nd edn, 1989.
J. Piette J. Photochem. Photobiol., B 1991 11 241.
M. J. Steinbeck A. U. Khan M. J. Karnovsky J. Biol. Chem. 1992 267 13425.
T. W. Stief Med. Hypoth. 2003 60.
R. J. Wagner P. A. Motchnik R. Stocker H. Sies B. N. Ames J. Biol. Chem. 1993 268 18502.
B. Heyne D. Brault M.-P. Fontaine-Aupart S. Kohnen F. Tfibel A. Mouithys-Mickalad G. Deby-Dupont P. Hans M. Hoebeke Biochim. Biophys. Acta 2005 1724 100.
B. Heyne S. Kohnen D. Brault A. Mouithys-Mickalad F. Tfibel P. Hans M.-P. Fontaine-Aupart M. Hoebeke Photochem. Photobiol. Sci. 2003 2 939.
D. V. Bent E. Hayon J. Am. Chem. Soc. 1975 97 2599.
J. Feitelson E. Hayon A. Treinin J. Am. Chem. Soc. 1973 95 1025.
E. J. Land G. Porter Trans. Faraday Soc. 1963 59 2016.
G. V. Buxton C. L. Greenstock W. P. Helman R. A. B. J. Phys. Chem. Ref. Data 1988 17 513.
H. Seki M. Imamura Bull. Chem. Soc. Jpn. 1971 44 1538.
G. Kolher N. Getoff Chem. Phys. Lett. 1974 26 525.
J. R. Lakowicz, Principles of fluorescence spectroscopy, Plenium, New York, N. Y., 2nd edn, 1999.
A. R. Al, Rabaa F. Tfibel F. Merola P. Pernot M.-P. Fontaine-Aupart J. Chem. Soc., Perkin Trans. 1999 2 341.
M.-P. Fontaine-Aupart E. Renault L. Brian J. F. Delouis M. Gardes-Albert J. Photochem. Photobiol., A 1995 90 95.
D. L. Gerrard W. F. Maddams Spectrochim. Acta, Part A 1978 34A 1205.
D. L. Gerrard W. F. Maddams Spectrochim. Acta, Part A 1978 34A 1219.
D. L. Gerrard W. F. Maddams P. J. Tucker Spectrochim. Acta, Part A 1978 34A 1225.
G. Nemethy A. Ray J. Phys. Chem. 1973 77 64.
J. Zechner G. Kolher G. Grabner N. Getoff Can. J. Chem. 1980 58 2006.
T. J. Stone W. A. Waters J. Chem. Soc. 1964 213.
R. M. Borges, dos Santos J. A. Martinho Simoes J. Phys. Chem. Ref. Data 1998 27 707.
R. V. Bensasson, E. J. Land and T. G. Truscott, Flash photolysis and pulse radiolysis, Pergamon Press, Oxford, UK, 1983.
K. N. Jha G. L. Bolton G. R. Freeman J. Phys. Chem. 1972 76 3876.
O. Brede H. Orthner V. Zubarev R. Hermann J. Phys. Chem. 1996 100 7097.
T. A. Gadosy D. Shukla L. J. Johnston J. Phys. Chem. A 1999 103 8834.
R. Hermann S. Naumov G. R. Mahalaxmi O. Brede Chem. Phys. Lett. 2000 324 265.
S. L. Murov, Handbook of Photochemistry, Marcel Dekker, New York, N. Y., 1973.
D. O. Martire C. Evans S. G. Bertolotti S. E. Braslavsky N. A. Garcia Chemosphere 1993 26 1691.
B. H. J. Bielski H. W. A. Richter J. Am. Chem. Soc. 1977 99 3019.
A. Michaeli J. Feitelson Photochem. Photobiol. 1994 59 284.
G. Kolher G. Kittel N. Getoff J. Photochem. 1982 18 19.
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.
