94608-23-8 Usage
Description
Resveratrol is a potent antioxidant found in grapes and red wine that also has anti-proliferative, anti-neoplastic and anti-angiogenic activities. In addition, resveratrol activates sirtuins and, in yeast, extends lifespan. cis-trismethoxy Resveratrol is a potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells. It inhibits tubulin polymerization in a dose-dependent manner (IC50 = 4 μM) and inhibits enzymes involved in the synthesis of the polyamines, putrescine, and spermidine. trans-trismethoxy Resveratrol has superior pharmacokinetic characteristics when compared with resveratrol, including greater plasma exposure, longer elimination half-life, and lower clearance.
Uses
Different sources of media describe the Uses of 94608-23-8 differently. You can refer to the following data:
1. Resveratrol is a potent antioxidant found in grapes and red wine that also has anti-proliferative, anti-neoplastic and anti-angiogenic activities. In addition, resveratrol activates sirtuins and, in yeast, extends lifespan. cis-trismethoxy Resveratrol is a potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells. It inhibits tubulin polymerization in a dose-dependent manner (IC50 = 4 μM) and inhibits enzymes involved in the synthesis of the polyamines, putrescine, and spermidine. trans-trismethoxy Resveratrol has superior pharmacokinetic characteristics when compared with resveratrol, including greater plasma exposure, longer elimination half-life, and lower clearance.
2. cis-trismethoxy Resveratrol is a potent antioxidant found in grapes and red wine. Also, it is a resveratrol analog with increased antiproliferative activity towards a number of cancer cell lines.
in vitro
cis-trismethoxy resveratrol at 0.3 microm could exert a 80% growth inhibition of human colon cancer caco-2 cells and arrest growth completely at 0.4 microm. the cis conformation of cis-trismethoxy resveratrol was also 100-fold more potent than the trans isomer. cis-trismethoxy resveratrol was able to cause cell cycle arrest at the g2/m phase transition and inhibit tubulin polymerization dose-dependently, leading to the depletion of the polyamines, putrescine and spermidine. in addition, cis-trismethoxy resveratrol inhibited partially colchicine binding to its binding site on tubulin [1].
in vivo
previous study found that from the angle of pharmacokinetics, cis-trismethoxy resveratrol appeared to be a superior analog of resveratrol since it was orally available and showed greater plasma exposure, longer elimination half-life and lower clearance. due to the superior pharmacokinetic characteristics of cis-trismethoxy resveratrol had, its potentials as a preventive or therapeutic agent in resveratrol-effective diseases would be considered [2].
IC 50
4 microm for tubulin polymerization
references
[1] schneider, y. ,chabert, p.,stutzmann, j., et al. resveratrol analog (z)-3,5,4'-trimethoxystilbene is a potent anti-mitotic drug inhibiting tubulin polymerization. international journal of cancer 107, 189-196 (2003).[2] lin, h. s. and ho, p.c. a rapid hplc method for the quantification of 3,5,4'-trimethoxy-trans-stilbene (tms) in rat plasma and its application in pharmacokinetic study. journal of pharmaceutical & biomedical analysis 49, 387-392 (2009).
Check Digit Verification of cas no
The CAS Registry Mumber 94608-23-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,6,0 and 8 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 94608-23:
(7*9)+(6*4)+(5*6)+(4*0)+(3*8)+(2*2)+(1*3)=148
148 % 10 = 8
So 94608-23-8 is a valid CAS Registry Number.
94608-23-8Relevant articles and documents
(Z)-(2-bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis
Woerly, Eric M.,Struble, Justin R.,Palyam, Nagarjuna,O'Hara, Sean P.,Burke, Martin D.
, p. 4333 - 4343 (2011)
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (Z)-(2-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very
Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
, p. 817 - 826 (2020/08/17)
Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
Copper-catalysed, diboron-mediated: Cis -dideuterated semihydrogenation of alkynes with heavy water
Han, Xiaowei,Hu, Jiefeng,Chen, Cheng,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 6922 - 6925 (2019/06/18)
Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.
