Photoswitchable anticancer activity via trans–cis isomerization of a combretastatin A-4 analog?
Organic & Biomolecular Chemistry Pub Date: 2015-10-27 DOI: 10.1039/C5OB02005K
Abstract
Combretastatin A-4 (CA4) is highly potent anticancer drug that acts as an inhibitor of tubulin polymerization. The core of the CA4 structure contains a cis-stilbene, and it is known that the trans isomer is significantly less potent. We prepared an azobenzene analog of CA4 (Azo-CA4) that shows 13–35 fold enhancement in potency upon illumination. EC50 values in the light were in the mid nM range. Due to its ability to thermally revert to less toxic trans form, Azo-CA4 also has the ability to automatically turn its activity off with time. Azo-CA4 is less potent than CA-4 because it degrades in the presence of glutathione as evidenced by UV-Vis spectroscopy and ESI-MS. Nevertheless, Azo-CA4 represents a promising strategy for switchable potency for treatment of cancer.
Recommended Literature
- [1] An atomistic mechanism for the degradation of perovskite solar cells by trapped charge? Eunhak Lim,Jiyoung Heo,Seong Keun KimNanoscale, 2019,11, 11369-11378 10.1039/C9NR02193K
- [2] An integrated microfluidic 3D tumor system for parallel and high-throughput chemotherapy evaluation? Dan Liu,Rui Hu,Zhongchao Huang,Meilin Sun,Kai HanAnalyst, 2020,145, 6447-6455 10.1039/D0AN01229G
- [3] An atomic scale study of defects in Co2FeAl Ravi Kumar Yadav,R. GovindarajPhys. Chem. Chem. Phys., 2020,22, 26876-26886 10.1039/D0CP04572A
- [4] An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning? Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao DuanNanoscale, 2016,8, 19541-19550 10.1039/C6NR07585A
- [5] An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems RabailGul,MariamMir,MurtazaNAli 10.1177/08853282231160212
- [6] Aggregation-induced emission based on a fluorinated macrocycle: visualizing spontaneous and ultrafast solid-state molecular motions at room temperature via F?F interactions? Mei Zhang,Jingjing Guo,Tingting Liu,Zhanyu He,Majeed Irfan,Zujin Zhao,Zhuo ZengJ. Mater. Chem. C, 2020,8, 14919-14924 10.1039/D0TC03797D
- [7] An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction? Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin JinJ. Mater. Chem. C, 2020,8, 192-200 10.1039/C9TC05297F
- [8] An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay? Suji Lee,Min Su HanChem. Commun., 2021,57, 9450-9453 10.1039/D1CC03638F
- [9] Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes? Chandran Rajendran,Govindaswamy Satishkumar,Charlotte Lang,Eric M. GaigneauxCatal. Sci. Technol., 2020,10, 2583-2592 10.1039/D0CY00471E
- [10] An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform? Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao YouAnalyst, 2015,140, 1827-1831 10.1039/C4AN01953A
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)