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| 2. |
- Danieli, B, et al.
(författare)
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Synthesis and biological evaluation of paclitaxel-thiocoichicine hybrids
- 2004
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Ingår i: Chemistry and Biodiversity. - : Wiley. - 1612-1872 .- 1612-1880. ; 1:2, s. 327-345
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Tidskriftsartikel (refereegranskat)abstract
- The bifunctional taxoid-colchicinoid hybrids 6-8 were synthesized and evaluated in assays of cytotoxicity and tubulin assembly/disassembly. All compounds showed a high degree of cytotoxicity, but, while 6 and 7 behaved as bifunctional tubulin binders not unlike an equimolecular mixture of taxol and thiocolchicine, 8 was surprisingly devoid of tubulin activity, acting on a distinct and yet to identify molecular target.
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| 3. |
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| 4. |
- Appendino, G, et al.
(författare)
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A new P-glycoprotein inhibitor from the caper spurge (Euphorbia lathyris).
- 2003
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 66:1, s. 140-142
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Tidskriftsartikel (refereegranskat)abstract
- The macrocyclic lathyrane polyester Euphorbia factor L10 (1a) has been obtained from the seeds of the caper spurge (E. lathyris). The interaction of L10 (1a) and its acetyl derivative (1b) with P-glycoprotein, a multidrug transporter overexpressed in cancer cells and responsible for resistance to chemotherapy, was investigated. The results established lathyrane diterpenoids as a novel chemotype for P-glycoprotein inhibitors.
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| 5. |
- Appendino, G, et al.
(författare)
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SERCA-inhibiting activity of C-19 terpenolides from Thapsia garganica and their possible biogenesis
- 2005
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 68:8, s. 1213-1217
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Tidskriftsartikel (refereegranskat)abstract
- An investigation of Thapsia garganica afforded a series of tetracyclic C-19 dilactones, whose production was dependent on the time and location of the collection. These unusual tetrahomosesquiterpenoids are presumably biosynthesized via a carbon dioxide-triggered electrophilic polyolefin cyclization. Despite the structural differences with thapsigargin, these compounds showed SERCA-inhibiting properties.
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| 6. |
- Appendino, G, et al.
(författare)
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Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications
- 2004
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 67:2, s. 184-188
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Tidskriftsartikel (refereegranskat)abstract
- The acylative modification of IDN 5390 (3a), a 7,8-secotaxoid under preclinical development, was investigated. A modest decrease of potency was observed upon acylation of the primary and the enolic hydroxyls, suggesting that, just like in paclitaxel, the hydroxyl groups in the upper right-hand sector are not critical for cytotoxicity. The activity of these analogues, and especially of the chemically robust carbonates 3c and 3d, makes it unlikely that the activity of IDN 5390 is due to in vivo oxidation to a fledgling 7-aldehyde and re-aldolization to the corresponding taxane derivative.
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| 7. |
- Appendino, G, et al.
(författare)
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The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.
- 2003
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Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; 2003:22, s. 4422-4431
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Tidskriftsartikel (refereegranskat)abstract
- The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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| 8. |
- Appendino, G, et al.
(författare)
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Antibacterial galloylated alkylphloroglucinol glucosides from myrtle (Myrtus communis)
- 2006
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 69:2, s. 251-254
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Tidskriftsartikel (refereegranskat)abstract
- An investigation of the polar glycosidic fraction from the leaves of myrtle afforded four galloylated nonprenylated phloroglucinol glucosides (3a-d) related to the endoperoxide hormone G3 (4) in terms of structure and biogenesis. Despite their close similarity, significant antibacterial activity was shown only by one of these compounds (3b, gallomyrtucommulone B), while the G3 hormone (4) was inactive.
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| 10. |
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