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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Bioorganic & medicinal chemistry | ||||
| Verlag: | Elsevier | ||||
| Band: | 9 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 8 | ||||
| Seitenbereich: | S. 2189-2194 | ||||
| Datum: | 2001 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 136:266 1-6 Pharmacology 52-90-4 (Cysteine); 70-18-8 (Glutathione) Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), BIOL (Biological study) (glutathione and cysteine levels effect on helenanolide type sesquiterpene lactones cytotoxicity against KB cells); 6754-13-8 (Helenalin); 36505-53-0 (11,13-Dihydrohelenalin acetate); 78853-98-2 (Chamissonolide); 190957-10-9; 374937-03-8; 374937-04-9 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (glutathione and cysteine levels effect on helenanolide type sesquiterpene lactones cytotoxicity against KB cells) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Cytotoxic agents Sulfhydryl group (glutathione and cysteine levels effect on helenanolide type sesquiterpene lactones cytotoxicity against KB cells) Sesquiterpenes Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (lactones glutathione and cysteine levels effect on helenanolide type sesquiterpene lactones cytotoxicity against KB cells) glutathione cysteine helenanolide sesquiterpene lactone cytotoxicity thiol | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Nein | ||||
| Dokumenten-ID: | 17195 |
Zusammenfassung
The biol. activities of sesquiterpene lactones have been attributed to their reactivity with the cysteine residues of functional proteins forming covalent bonds via Michael type addn. In the present study we investigated the influence of different l-cysteine (cys) and glutathione (GSH) concns. on the cytotoxicity of the sesquiterpene lactones (STLs) helenalin, 11alpha ,13-dihydrohelenalin acetate ...
Zusammenfassung
The biol. activities of sesquiterpene lactones have been attributed to their reactivity with the cysteine residues of functional proteins forming covalent bonds via Michael type addn. In the present study we investigated the influence of different l-cysteine (cys) and glutathione (GSH) concns. on the cytotoxicity of the sesquiterpene lactones (STLs) helenalin, 11alpha ,13-dihydrohelenalin acetate and chamissonolide against KB cells. Due to the significantly higher reactivity of the alpha -methylene-gamma -lactone (ML) towards cys as compared with the cyclopentenone (CP) site at physiol. pH, addn. of 20, 50 and 100 molar equivalents of cys decreased the cytotoxicity of helenalin and chamissonolide, whereas the cytotoxicity of 11alpha ,13-dihydrohelenalin acetate remained unaffected. In contrast, the influence of GSH addn. on the cytotoxicity of 11alpha ,13-dihydrohelenalin acetate depends on the concn. of GSH added. Concn.-effect curves obtained for chamissonolide and GSH resembled the decline in cytotoxicity after cys addn. Helenalin showed a biphasic shape of the concn.-effect curve for the 100:1 GSH/helenalin ratio resembling at higher doses the chamissonolide and in lower doses the 11alpha ,13-dihydrohelenalin acetate curve at 50-fold excess. These results can be explained by the different reactivity and equil. conditions for thiol addn. of the two reactive centers of bifunctional STLs in cellular test systems and verified a clear correlation between the different reactivity of their electrophilic centers and the obsd. biol. effects in in-vitro cell systems.
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