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Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and chelerythrine have the potential to form molecular complexes with DNA structures and have attracted recent attention for their possible clinical and pharmacological utility. This review focuses on the interaction of these alkaloids with polymorphic DNA structures (B-form, Z-form, HL-form, and triple helical form) reported by several research groups employing various physical techniques such as spectrophotometry, spectrofluorimetry, circular dichroism, NMR spectroscopy, thermal melting, viscometry as well as thermodynamic analysis by isothermal titration calorimetry and differential scanning calorimetry to elucidate the mode and mechanism of action at the molecular level to determine the structure-activity relationship. DNA binding properties of these alkaloids are interpreted in relation to their biological activity. 相似文献
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François Tillequin 《Phytochemistry Reviews》2007,6(1):65-79
The chemical diversity of alkaloids in the Rutaceae is correlated with biosynthetic pathways involving various aromatic amino
acid precursors, tyrosine, tryptophan, histidine, and anthranilic acid. The interest of rutaceous polyheteroaromatic alkaloids
as models for the development of anticancer agents relies on their frequent ability to interact with DNA or with systems involved
in the control of its topology, repair, and replication. Fagaronine and nitidine, from Zanthoxylum, demonstrate antileukemic activity, associated with topoisomerases inhibition. Evodiamine from Euodia rutaecarpa, displays antimetastatic properties. The pyranoacridone acronycine, from Sarcomelicope, exhibits antitumor activity against a broad spectrum of solid tumors. Development of synthetic analogues based on this latter
natural product template followed the isolation of the unstable acronycine epoxide, which led to a hypothesis of bioactivation
of acronycine by transformation of the 1,2-double bond into the corresponding oxirane. 1,2-Diacyloxy-1,2-dihydroacronycine
derivatives exhibited antitumor properties, with a broadened spectrum of activity and an increased potency. The demonstration
that acronycine interacted with DNA led to develop benzo[a], [b], and [c]acronycine analogs. Benzo[a] and [b] derivatives displayed significant antitumor activities. 1,2-Dihydroxy-1,2-dihydrobenzo[b]acronycine esters and diesters were active in human orthotopic models of cancers xenografted in nude mice. The activity of
these compounds was correlated with their ability to give covalent adducts with DNA, involving reaction between the N-2 amino
group of guanines and the ester group at the benzylic position of the drug. Cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine, currently developed under the code S23906-1, successfully underwent phase I and is currently under phase II clinical
trials. 相似文献
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Enguerran Vanquelef Jean-Jacques Hélesbeux Olivier Duval Eric Debiton Chantal Barthomeuf Christian Jarry 《Journal of enzyme inhibition and medicinal chemistry》2013,28(5):647-654
Fagaronine derivatives syntheses were optimized and their effect on PC3 androgen-independent prostate cell line was evaluated. An assessment of the lipophilicity of the benzo[c]phenanthridine derivatives was achieved at pH 7.4 and et 6.7 by determining log D. 相似文献
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Enguerran Vanquelef Maryvonne Amoros Joel Boustie Michael A. Lynch Roger D. Waigh 《Journal of enzyme inhibition and medicinal chemistry》2013,28(6):481-487
The synthesis of benzo[c]phenanthridine alkaloid derivatives is described. In vitro antiviral activity against herpes simplex type 1 (HSV1) has been investigated. Contrary to the natural product fagaronine, which did not have any activity in the HSV1 antiviral tests, four 12-alkoxy derivatives showed good activity demonstrating the importance of the 12-substitution in the structure-activity relationships. 相似文献
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