Structure–activity relationship of selected polyphenol derivatives as inhibitors of Bax/Bcl-xL interaction
Abstract
This paper describes the synthesis of nine selected diaryl/heteroaryl-containing phenol and polyphenol derivatives which have been evaluated against Bax/Bcl-xL interaction in comparison with ABT-737. Using a BRET assay, six of these derivatives exhibit activity comparable to ABT-737 to disrupt Bax/Bcl-xL interaction. These preliminary results demonstrate that such polyphenol-derived molecules are attractive compounds regarding anticancer activity and that the phenol at position 3 is important regarding disruption of Bax/Bcl-xL interaction.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Cites
An inhibitor of Bcl-2 family proteins induces regression of solid tumours
Oltersdorf, T., Elmore, S. W., Shoemaker, A. R., Armstrong, R. C., Augeri, D. J., Belli, B., Bruncko, M., Deckwerth, T. L., Dinges, J., Hajduk, P. J., et al. (2005) · Nature · doi:10.1038/nature03579 · Cited by 3,407 · see citing works
Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis
Quideau, S., Deffieux, D., Douat, C., & Pouységu, L. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201000044 · Cited by 2,756 · see citing works
Genetic control of programmed cell death in the nematode C. elegans
Ellis, H. (1986) · Cell · doi:10.1016/0092-8674(86)90004-8 · Cited by 1,828 · see citing works
van Delft, M. F., Wei, A. H., Mason, K. D., Vandenberg, C. J., Chen, L., Czabotar, P. E., Willis, S. N., Scott, C. L., Day, C. L., Cory, S., et al. (2006) · Cancer Cell · doi:10.1016/j.ccr.2006.08.027 · Cited by 1,237 · see citing works
Hengartner, M. O., & Horvitz, H. R. (1994) · Cell · doi:10.1016/0092-8674(94)90506-1 · Cited by 1,167 · see citing works
Meier, P., Finch, A. J., & Evan, G. I. (2000) · Nature · doi:10.1038/35037734 · Cited by 1,027 · see citing works
Konopleva, M. Y., Contractor, R., Tsao, T., Samudio, I. J., Ruvolo, P. P., Kitada, S., Deng, X., Zhai, D., Shi, Y.-X., Sneed, T. B., et al. (2006) · Cancer Cell · doi:10.1016/j.ccr.2006.10.006 · Cited by 1,020 · see citing works
BCL-2 family antagonists for cancer therapy
Lessène, G., Czabotar, P. E., & Colman, P. M. (2008) · Nature Reviews Drug Discovery · doi:10.1038/nrd2658 · Cited by 623 · see citing works
Prevention of Programmed Cell Death in Caenorhabditis elegans by Human bcl-2
Vaux, D. L., Weissman, I. L., & Kim, S. K. (1992) · Science · doi:10.1126/science.1470921 · Cited by 614 · see citing works
Moore, V. D. G., Brown, J. R., Certo, M. V., Love, T. M., Novina, C. D., & Letai, A. G. (2007) · Journal of Clinical Investigation · doi:10.1172/jci28281 · Cited by 604 · see citing works
Mcl‐1; the molecular regulation of protein function
Thomas, L. W., Lam, C. W., & Edwards, S. W. (2010) · FEBS Letters · doi:10.1016/j.febslet.2010.05.061 · Cited by 540 · see citing works
Deng, J., Carlson, N. E., Takeyama, K., Cin, P. D., Shipp, M. A., & Letai, A. G. (2007) · Cancer Cell · doi:10.1016/j.ccr.2007.07.001 · Cited by 509 · see citing works
Apoptosis-targeted therapies for cancer
Reed, J. C. (2003) · Cancer Cell · doi:10.1016/s1535-6108(02)00241-6 · Cited by 502 · see citing works
Brough, P. A., Aherne, W., Barril, X., Borgognoni, J., Boxall, K. J., Cansfield, J. E., Cheung, K.-M. J., Collins, I., Davies, N. G. M., Drysdale, M. J., et al. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm701018h · Cited by 449 · see citing works
Mechanisms of apoptosis avoidance in cancer
Reed, J. C. (1999) · Current Opinion in Oncology · doi:10.1097/00001622-199901000-00014 · Cited by 371 · see citing works
Verdine, G. L., & Walensky, L. D. (2007) · Clinical Cancer Research · doi:10.1158/1078-0432.ccr-07-2184 · Cited by 362 · see citing works
Bcl-2 inhibitors: small molecules with a big impact on cancer therapy
Vogler, M., Dinsdale, D. D., Dyer, M. J. S., & Cohen, G. M. (2008) · Cell Death and Differentiation · doi:10.1038/cdd.2008.137 · Cited by 359 · see citing works
Terrillon, S., Durroux, T., Mouillac, B., Breit, A., Ayoub, M. A., Taulan‐Cadars, M., Jockers, R., Barberis, C., & Bouvier, M. (2003) · Molecular Endocrinology · doi:10.1210/me.2002-0222 · Cited by 323 · see citing works
Structure-Based Design of Potent Small-Molecule Inhibitors of Anti-Apoptotic Bcl-2 Proteins
Wang, G., Nikolovska‐Coleska, Z., Yang, C., Wang, R., Tang, G., Guo, J., Shangary, S. K., Qiu, S., Gao, W., Yang, D., et al. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm060460o · Cited by 293 · see citing works
Mimicking the BH3 domain to kill cancer cells
Chonghaile, T. N., & Letai, A. G. (2008) · Oncogene · doi:10.1038/onc.2009.52 · Cited by 268 · see citing works
BCL-2 in the crosshairs: tipping the balance of life and death
Walensky, L. D. (2006) · Cell Death and Differentiation · doi:10.1038/sj.cdd.4401992 · Cited by 245 · see citing works
Polyphenols and cancer cell growth
Kampa, M., Nifli, A., Notas, G., & Castanas, E. (2007) · Springer eBooks · doi:10.1007/112_2006_0702 · Cited by 193 · see citing works
Unique Biology of Mcl-1: Therapeutic Opportunities in Cancer
Shore, G. C., & Warr, M. R. (2008) · Current Molecular Medicine · doi:10.2174/156652408783769580 · Cited by 193 · see citing works
BH3 mimetics to improve cancer therapy; mechanisms and examples
Zhang, L., Ming, L., & Yu, J. (2007) · Drug Resistance Updates · doi:10.1016/j.drup.2007.08.002 · Cited by 139 · see citing works
Manero, F., Gautier, F., Gallenne, T., Cauquil, N., Gree, D. M., Cartron, P., Geneste, O., Gree, R. L., Vallette, F. M., & Juin, P. P. (2006) · Cancer Research · doi:10.1158/0008-5472.can-05-2097 · Cited by 134 · see citing works
Self-citationZhao, J., Dimaras, H., Massey, C., Xu, X., Huang, D., Li, B., Chan, H. S. L., & Gallie, B. L. (2011) · Journal of Clinical Oncology · doi:10.1200/jco.2010.32.5332 · Cited by 120 · see citing works
Non‐peptidic small molecule inhibitors against Bcl‐2 for cancer therapy
Azmi, A. S., & Mohammad, R. M. (2008) · Journal of Cellular Physiology · doi:10.1002/jcp.21567 · Cited by 119 · see citing works
Drugs targeting Bcl-2 family members as an emerging strategy in cancer
Leber, B. F., Geng, F., Kale, J., & Andrews, D. W. (2010) · Expert Reviews in Molecular Medicine · doi:10.1017/s1462399410001572 · Cited by 88 · see citing works
Bcl-2 family members as molecular targets in cancer therapy
Marzo, I., & Naval, J. (2008) · Biochemical Pharmacology · doi:10.1016/j.bcp.2008.06.009 · Cited by 87 · see citing works
Aminoglycoside suppression of nonsense mutations in severe hemophilia
James, P. D., Raut, S., Rivard, G., Poon, M., Warner, M., McKenna, S., Leggo, J., & Lillicrap, D. (2005) · Blood · doi:10.1182/blood-2005-03-1307 · Cited by 85 · see citing works
Zeitlin, B. D., Zeitlin, I. J., & Nor, J. E. (2008) · Journal of Clinical Oncology · doi:10.1200/jco.2007.15.7693 · Cited by 81 · see citing works
Acylpyrogallols as Inhibitors of Antiapoptotic Bcl-2 Proteins
Tang, G., Nikolovska‐Coleska, Z., Qiu, S., Yang, C., Guo, J., & Wang, S. (2008) · Journal of Medicinal Chemistry · doi:10.1021/jm701358v · Cited by 81 · see citing works
Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol
Amblard, F., Govindarajan, B., Lefkove, B., Rapp, K. L., Detorio, M., Arbiser, J. L., & Schinazi, R. F. (2007) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2007.06.024 · Cited by 68 · see citing works
Shooting at survivors: Bcl-2 family members as drug targets for cancer
Juin, P. P., Geneste, O., Raimbaud, E., & Hickman, J. A. (2003) · Biochimica et Biophysica Acta (BBA) - Molecular Cell Research · doi:10.1016/j.bbamcr.2003.10.010 · Cited by 64 · see citing works
Self-citationPyrogallol-Based Molecules as Potent Inhibitors of the Antiapoptotic Bcl-2 Proteins
Tang, G., Yang, C., Nikolovska‐Coleska, Z., Guo, J., Qiu, S., Wang, R., Gao, W., Wang, G., Stuckey, J. A., Krajewski, K., et al. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm061400l · Cited by 48 · see citing works
The synthesis of new, selected analogues of the pro-apoptotic and anticancer molecule HA 14-1
Gree, D. M., Vorin, S., Manthati, V. L., Caïjo, F., Viault, G., Manero, F., Juin, P. P., & Gree, R. L. (2008) · Tetrahedron Letters · doi:10.1016/j.tetlet.2008.03.070 · Cited by 46 · see citing works
Self-citationInsulin Breast Cancer Connection: Confirmatory Data Set the Stage for Better Care
DeCensi, A., & Gennari, A. (2010) · Journal of Clinical Oncology · doi:10.1200/jco.2010.32.3022 · Cited by 45 · see citing works
HA14-1, a small molecule inhibitor of Bcl-2, bypasses chemoresistance in leukaemia cells
Oliver, L., Mahé, B., Gree, R. L., Vallette, F. M., & Juin, P. P. (2007) · Leukemia Research · doi:10.1016/j.leukres.2006.11.010 · Cited by 37 · see citing works
Self-citationBertini, S., Calderone, V., Carboni, I., Maffei, R., Martelli, A., Martinelli, A., Minutolo, F., Rajabi, M., Testai, L., Tuccinardi, T., et al. (2010) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2010.07.059 · Cited by 36 · see citing works
Bax Activation by Engagement with, Then Release from, the BH3 Binding Site of Bcl-x L
Gautier, F., Guillemin, Y., Cartron, P., Gallenne, T., Cauquil, N., Diguarher, T. L., Casara, P., Vallette, F. M., Manon, S., Hickman, J. A., et al. (2010) · Molecular and Cellular Biology · doi:10.1128/mcb.00161-10 · Cited by 35 · see citing works
Self-citationThe first synthesis of 2-amino-1,4-dihydroquinolines
Viault, G., Gree, D. M., Roisnel, T., Chandrasekhar, S., & Gree, R. L. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.10.018 · Cited by 18 · see citing works
Miscellaneous cancers associated with AIDS
Cohen, P. (1989) · Current Opinion in Oncology · doi:10.1097/00001622-198910000-00014 · Cited by 9 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Modulators of Protein–Protein Interactions
Milroy, L.-G., Grossmann, T. N., Hennig, S., Brunsveld, L., & Ottmann, C. (2014) · Chemical Reviews · doi:10.1021/cr400698c · Cited by 497 · see citing works
Bcl-xL controls a switch between cell death modes during mitotic arrest
Bah, N. K., Maillet, L., Ryan, J. A., Dubreil, S., Gautier, F., Letai, A. G., Juin, P. P., & Barillé‐Nion, S. (2014) · Cell Death and Disease · doi:10.1038/cddis.2014.251 · Cited by 61 · see citing works
Self-citationGloaguen, C., Voisin‐Chiret, A. S., Santos, J. S. O., Fogha, J., Gautier, F., Giorgi, M. D., Burzicki, G., Perato, S., Pétigny-Lechartier, C., Simonin, K., et al. (2015) · Journal of Medicinal Chemistry · doi:10.1021/jm500672y · Cited by 53 · see citing works
Self-citationProtein–Protein Interactions as Drug Targets
Skwarczynska, M., & Ottmann, C. (2015) · Future Medicinal Chemistry · doi:10.4155/fmc.15.138 · Cited by 50 · see citing works
Valavanidis, A., & Vlachogianni, T. (2013) · Studies in natural products chemistry · doi:10.1016/b978-0-444-62615-8.00008-4 · Cited by 47 · see citing works
Yang, R., Tavares, M. T., Teixeira, S. F., Azevedo, R., Pietro, D. C., Fernandes, T. B., Ferreira, A. K., Trossini, G. H. G., Barbuto, J. A. M., & Parise‐Filho, R. (2016) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2016.07.065 · Cited by 15 · see citing works
Fu, D., Zhao, R.-H., Li, J., Yang, J., Mao, R.-W., Wu, B., Li, P., Zi, X., Zhang, Q., Cai, H., et al. (2017) · Molecular Diversity · doi:10.1007/s11030-017-9773-4 · Cited by 13 · see citing works
Vo, D. D., Gautier, F., Barillé‐Nion, S., Juin, P. P., Levoin, N., & Gree, R. L. (2014) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2014.02.035 · Cited by 9 · see citing works
Self-citationA combination of in silico and SAR studies to identify binding hot spots of Bcl-xL inhibitors
Levoin, N., Vo, D. D., Gautier, F., Barillé‐Nion, S., Juin, P. P., Tasseau, O., & Gree, R. L. (2015) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2015.02.060 · Cited by 9 · see citing works
Self-citationVo, D. D., Gautier, F., Barillé‐Nion, S., Juin, P. P., Levoin, N., & Gree, R. L. (2013) · Tetrahedron · doi:10.1016/j.tet.2013.11.060 · Cited by 7 · see citing works
Self-citationMurthy, A. V. R., Narendar, V., Kumar, N. S., Aparna, P., Bhavani, A. K. D., Gautier, F., Barillé‐Nion, S., Juin, P. P., Mosset, P., Gree, R. L., et al. (2018) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2018.10.069 · Cited by 5 · see citing works
Self-citationPaysant, H., Hedir, S., Justaud, F., Weiswald, L., Dine, A. N. E., Soulieman, A., Hachem, A., Elie, N., Brotin, É., Denoyelle, C., et al. (2021) · Organic & Biomolecular Chemistry · doi:10.1039/d1ob01521d · Cited by 4 · see citing works
- Authors
- Vo, D. D., Gautier, F., Juin, P., & Grée, R.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Inserm (FR)
- Venue
- European Journal of Medicinal Chemistry
- Publisher
- Elsevier BV
- Published
- 2012-05
- Volume
- 51
- Pages
- 286-293
- ISSN
- 0223-5234 (ISSN-L)
- OpenAlex
- W2079532359
- Cited by
- 14
- References
- 42
- Citations by year
- 2021: 2 · 2018: 1 · 2017: 2 · 2016: 1 · 2015: 3 · 2014: 3 · 2013: 2
- FWCI
- 1.03
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- European Journal of Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- Funders
- Ligue Contre le Cancer
- Servier
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Cell death mechanisms and regulation
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Physical Sciences › Computer Science › Computational Theory and Mathematics › Computational Drug Discovery Methods
- Keywords
- structure-activity relationship, polyphenol derivatives, ABT-737, anticancer agents, apoptosis
- MeSH terms
- Antineoplastic Agents, HeLa Cells, Humans, Protein Binding, Structure-Activity Relationship, Apoptosis, bcl-X Protein, bcl-2-Associated X Protein, Polyphenols
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review