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Literature DB >> 9632366

Structure-activity requirements for flavone cytotoxicity and binding to tubulin.

J A Beutler¹, E Hamel, A J Vlietinck, A Haemers, P Rajan, J N Roitman, J H Cardellina, M R Boyd.

Abstract

A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5, 7,3'-trihydroxyflavone, 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [3H]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

Entities: Chemical Disease Species

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Year: 1998 PMID： 9632366 DOI： 10.1021/jm970842h

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

16 in total

1. A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerization.

Authors: Yuko Ito; Akiko Kanamaru; Akihiro Tada
Journal: Mol Cell Biochem Date: 2006-10-07 Impact factor: 3.396

2. Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins.

Authors: Rongsheng E Wang; Clayton R Hunt; Jiawei Chen; John-Stephen Taylor
Journal: Bioorg Med Chem Date: 2011-07-13 Impact factor: 3.641

3. Casticin inhibits the activity of transcription factor Sp1 and the methylation of RECK in MGC803 gastric cancer cells.

Authors: Fan Yang; Kefei He; Li Huang; Lingyan Zhang; Aixue Liu; Jiren Zhang
Journal: Exp Ther Med Date: 2016-12-27 Impact factor: 2.447

4. 8-Formylophiopogonanone B induces ROS-mediated apoptosis in nasopharyngeal carcinoma CNE-1 cells.

Authors: Ya-Jing Zhang; Zhen-Lin Mu; Ping Deng; Yi-Dan Liang; Li-Chuan Wu; Ling-Ling Yang; Zhou Zhou; Zheng-Ping Yu
Journal: Toxicol Res (Camb) Date: 2021-09-06 Impact factor: 2.680

5. How to deal with low-resolution target structures: using SAR, ensemble docking, hydropathic analysis, and 3D-QSAR to definitively map the αβ-tubulin colchicine site.

Authors: Chenxiao Da; Susan L Mooberry; John T Gupton; Glen E Kellogg
Journal: J Med Chem Date: 2013-09-09 Impact factor: 7.446

Structure-activity requirements for flavone cytotoxicity and binding to tubulin.

1. A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerization.

2. Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins.

3. Casticin inhibits the activity of transcription factor Sp1 and the methylation of RECK in MGC803 gastric cancer cells.

4. 8-Formylophiopogonanone B induces ROS-mediated apoptosis in nasopharyngeal carcinoma CNE-1 cells.

5. How to deal with low-resolution target structures: using SAR, ensemble docking, hydropathic analysis, and 3D-QSAR to definitively map the αβ-tubulin colchicine site.

6. Flavonoid-induced morphological modifications of endothelial cells through microtubule stabilization.

7. The Elbs and Boyland-Sims peroxydisulfate oxidations.

8. Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates.

9. Breast cancer cell line toxicity of a flavonoid isolated from Baccharis densiflora.

10. Methoxylated Flavones from Salvia Mirzayanii Rech. f. and Esfand with Immunosuppressive Properties.