Colchicine and its various physicochemical and biological aspects

Sapra, Sameer; Bhalla, Yashika; Nandani,; Sharma, Sahil; Singh, Gagandip; Nepali, Kunal; Budhiraja, Abhishek; Dhar, K.L.

doi:10.1007/s00044-012-0077-z

Cited by 36 publications

(34 citation statements)

References 108 publications

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“…[3][4][5][6][7] This effect leads to the disruption of the mitotic spindle formation, arrest of the cell cycle in G2/M phase and, eventually, to apoptotic cell death. The origin of its biological effect lies in the ability to inhibit polymerisation of tubulin, the main constitutive protein of microtubules.…”

Section: An Alkaloid Isolated From Plants Of the Genusmentioning

confidence: 99%

Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties

et al. 2015

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Basing on the natural antimitotic agent allocolchicine as a lead structure, a series of novel indole-based allocolchicine congeners was synthesized and assessed in vitro for cytostatic properties. Several compounds exhibited potent antiproliferative and apoptosis-inducing activity towards lymphoma cells along with low unspecific cytotoxicity. The observed activity is supposed to result from the inhibition of microtubule assembly, as indicated by the tubulin polymerisation assay.

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Section: An Alkaloid Isolated From Plants Of the Genusmentioning

confidence: 99%

Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties

et al. 2015

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“…APM is a rapid, reversible antimicrotubule agent for plant cell cultures (Falconer and Seagull, 1987) and shows high affinity for plant tubulin (Hansen et al, 1998). Colchicine (COL), the best known antimitotic agent, is used to obtain polyploidy in several plant species (Dutt et al, 2010;Zhang et al, 2010) and for the treatment of several diseases such as gout, Behçet's disease, and familial Mediterranean fever in humans (Sapra et al, 2012). Due to its low affinity for plant tubulin, a high concentration of COL is required for use in plants (Dhooghe et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Genotoxicity of metaphase-arresting methods in barley

Temel

Gözükırmızı²

2015

Turk J Biol

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Amiprophos-methyl (APM) and colchicine (COL) are therapeutic agents and are also used in plant science. Cell cycle synchronization (CCS) is mediated by hydroxyurea (HU) and APM. The genotoxic effects of APM are unclear. In order to assess the genotoxicity of APM separately and with HU and then compare it with COL, we treated 2-day-old barley (Hordeum vulgare 'Bornova-92') seedlings with 8 µM APM for 2 h, 1.25 mM COL for 18 h, or 1.25 mM HU for 18 h and 4 µM APM for 2 h, with a final ice-cold water incubation. Following treatment, seedlings were recovered without any substance for 2 days. Genomic DNA samples were analyzed by random amplified polymorphic DNA, inter-simple sequence repeat, and inter-retrotransposon amplified polymorphisms. Polypeptide profiles were analyzed by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Mean genomic stability (GTS) values at the end of APM, COL, and CCS treatments were 83.6%, 83%, and 82.3%, respectively. Mean GTS values after recovery from APM, COL, and CCS treatments were 78.5%, 83.9%, and 78.7%, respectively. APM treatment resulted in altered polypeptide profiles during both treatment and recovery. The genotoxicity of APM and COL was similar, while the genotoxic effects of APM continued after removal. Only COL treatment caused retrotransposon activation. APM treatment caused appearance of new polypeptides, which continued after the removal of APM. Although the microtubule inhibitory effect of APM has been reported to be reversible, APM may cause genotoxic effects on plants, and the molecular effects of APM may not be reversible.

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“…The indane core is present in a large number of natural products [13,14] and dibenzocycloheptadiene moieties constitute the main scaffold of colchicine alkaloids, com-pounds with antimitotic, antitumor, and antivascular activity. [15] Despite the interesting biological properties of both types of molecules, the assembly of highly functionalized derivatives in a stereoselective manner has proved to be highly challenging, with a few exceptions. [13b, 16] Our study commenced with the reaction of ortho-vinylsubstituted N-(arylsulfonyl)acrylamides derivatives 1 (Table 1).…”

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confidence: 99%

Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions

et al. 2015

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Two highly stereoselective radical-mediated syntheses of densely functionalized indanes and dibenzocycloheptadienes from ortho-vinyl- and ortho-vinylaryl-substituted N-(arylsulfonyl)-acrylamides, respectively, are presented here. The chemoselective addition of in situ generated radicals (X(·)) onto the styrene moieties triggers an unprecedented reaction cascade, resulting in the formation of one new C-X bond and two new C-C bonds, a formal 1,4-aryl migration, and the extrusion of SO2 to generate an amidyl radical intermediate. This intermediate, upon H abstraction, leads to the observed 5- and 7-membered ring carbocyclic products, respectively, in a highly efficient manner.

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Colchicine and its various physicochemical and biological aspects

Cited by 36 publications

References 108 publications

Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties

Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties

Genotoxicity of metaphase-arresting methods in barley

Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions

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