Influence of Substituents on the Lappaconitine Acetylenic Derivatives Photodegradation
The natural alkaloid lappaconitine, the anthranilic acid ester, is used against arrhythmias in medical practice, but it undergoes significant photodegradation. The latter may be the cause of the drugs phototoxicity. Furthermore, other esters of anthranilic acid are also widely used in practice, for...
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| Veröffentlicht in: | Applied magnetic resonance 2015-05, Vol.46 (5), p.559-573 |
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| creator | Schlotgauer, A. A. Klimentiev, V. I. Kornievskaya, V. S. Polyakov, N. E. Stepanov, A. A. Vasilevsky, S. F. Leshina, T. V. |
| description | The natural alkaloid lappaconitine, the anthranilic acid ester, is used against arrhythmias in medical practice, but it undergoes significant photodegradation. The latter may be the cause of the drugs phototoxicity. Furthermore, other esters of anthranilic acid are also widely used in practice, for example, as UV filters; so their photostability is an important characteristic. Thus, the improvement of these compounds resistance against light irradiation is the issue of the day. This work has shown that the appending of a substituent through the acetylene bridge into the anthranilic acid aromatic ring can significantly decrease the lappaconine derivatives photodegradation degree. The photodegradation process, according to the chemically induced dynamic nuclear polarization (CIDNP) analysis, begins with intramolecular or intermolecular reversible electron transfer (ET) with subsequent cleavage of the ester bond. The main product of the photolysis is the quaternary ammonium salt of 20-ethyl-1-α,14-α,16-β-trimethoxyaconitane-4,8,9-triol (lappaconine) of substituted anthranilic acid. It was demonstrated that the photodegradation of the lappaconitine acetylenic derivatives occurs from their triplet excited states and the substitution influences primarily the triplet reactive state formation effectivity.
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| doi_str_mv | 10.1007/s00723-015-0644-9 |
| format | Article |
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Graphical Abstract</description><subject>Acetylene</subject><subject>Aromatic compounds</subject><subject>Atoms and Molecules in Strong Fields</subject><subject>Decomposition</subject><subject>Electron transfer</subject><subject>Esters</subject><subject>Experiments</subject><subject>Free radicals</subject><subject>Hydrogen bonds</subject><subject>Laser Matter Interaction</subject><subject>Lasers</subject><subject>Light irradiation</subject><subject>Metabolites</subject><subject>Organic Chemistry</subject><subject>Photodegradation</subject><subject>Photolysis</subject><subject>Physical Chemistry</subject><subject>Physics</subject><subject>Physics and Astronomy</subject><subject>Quaternary ammonium salts</subject><subject>Solid State Physics</subject><subject>Spectroscopy/Spectrometry</subject><subject>Ultraviolet filters</subject><issn>0937-9347</issn><issn>1613-7507</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNp1kE1LAzEQhoMoWKs_wFvA82o-dpPNsdSvQkHBj2vI7k7aLTWpSbbQf2_KCp68zDDD887Ag9A1JbeUEHkXc2G8ILQqiCjLQp2gCRWUF7Ii8hRNiOKyULyU5-gixg3JYE3lBH0unN0O4FrA3uK3oYmpT3lOEXuH0xrw0ux2pvWuT70DPGshHbbg-hbfQ-j3JvV7iPh17ZPvYBVMlzfeXaIza7YRrn77FH08PrzPn4vly9NiPlsWLa9FKjrbNFaVwnZGyJJxzhpFW24lKQ0RqqUVA8YsiNoyKazlVddUNYFSNgQaJfgU3Yx3d8F_DxCT3vghuPxSM0WlqkUpZaboSLXBxxjA6l3ov0w4aEr0UZ8e9elsRR_1aZUzbMzEzLoVhL_L_4d-ADXXc7c</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Schlotgauer, A. 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Thus, the improvement of these compounds resistance against light irradiation is the issue of the day. This work has shown that the appending of a substituent through the acetylene bridge into the anthranilic acid aromatic ring can significantly decrease the lappaconine derivatives photodegradation degree. The photodegradation process, according to the chemically induced dynamic nuclear polarization (CIDNP) analysis, begins with intramolecular or intermolecular reversible electron transfer (ET) with subsequent cleavage of the ester bond. The main product of the photolysis is the quaternary ammonium salt of 20-ethyl-1-α,14-α,16-β-trimethoxyaconitane-4,8,9-triol (lappaconine) of substituted anthranilic acid. It was demonstrated that the photodegradation of the lappaconitine acetylenic derivatives occurs from their triplet excited states and the substitution influences primarily the triplet reactive state formation effectivity.
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| subjects | Acetylene Aromatic compounds Atoms and Molecules in Strong Fields Decomposition Electron transfer Esters Experiments Free radicals Hydrogen bonds Laser Matter Interaction Lasers Light irradiation Metabolites Organic Chemistry Photodegradation Photolysis Physical Chemistry Physics Physics and Astronomy Quaternary ammonium salts Solid State Physics Spectroscopy/Spectrometry Ultraviolet filters |
| title | Influence of Substituents on the Lappaconitine Acetylenic Derivatives Photodegradation |
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