Lipophilic pyridinium bisphosphonates: potent gammadelta T cell stimulators.
作者信息
Zhang Yonghui, Cao Rong, Yin Fenglin, Lin Fu-Yang, Wang Hong, Krysiak Kilannin, No Joo-Hwan, Mukkamala Dushyant, Houlihan Kevin, Li Jikun, Morita Craig T, Oldfield Eric
机构信息
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA.
出版信息
Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1136-8. doi: 10.1002/anie.200905933.
Abstract
摘要
相似文献
1
Lipophilic pyridinium bisphosphonates: potent gammadelta T cell stimulators.
Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1136-8. doi: 10.1002/anie.200905933.
2
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.
J Med Chem. 2004 Jan 15;47(2):375-84. doi: 10.1021/jm0303709.
3
Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption.
J Med Chem. 2005 Apr 21;48(8):2957-63. doi: 10.1021/jm040209d.
4
Contribution of Complementarity-Determining Region 3 of the T-Cell Receptor Vδ2 Chain to the Recognition of Aminobisphosphonates by Human γδ T-Cells.
Int J Hematol. 2004 May;79(4):369-76. doi: 10.1532/ijh97.03157.
5
Activation of γδ T cells by bisphosphonates.
Adv Exp Med Biol. 2010;658:11-20. doi: 10.1007/978-1-4419-1050-9_2.
6
Synthesis, stereochemistry and SAR of a series of minodronate analogues as RGGT inhibitors.
Eur J Med Chem. 2011 Oct;46(10):4820-6. doi: 10.1016/j.ejmech.2011.04.063. Epub 2011 May 7.
7
Vgamma2Vdelta2 T-cell receptor-mediated recognition of aminobisphosphonates.
Blood. 2001 Sep 1;98(5):1616-8. doi: 10.1182/blood.v98.5.1616.
8
Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase.
Bioorg Med Chem Lett. 2003 Oct 6;13(19):3231-5. doi: 10.1016/s0960-894x(03)00663-2.
9
Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates.
J Pharmacol Exp Ther. 2001 Feb;296(2):235-42.
10
Bovine gamma delta T cells and the function of gamma delta T cell specific WC1 co-receptors.
Cell Immunol. 2015 Jul;296(1):76-86. doi: 10.1016/j.cellimm.2015.05.003. Epub 2015 May 16.
引用本文的文献
1
Discovery and Evaluation of C6-Substituted Pyrazolopyrimidine-Based Bisphosphonate Inhibitors of the Human Geranylgeranyl Pyrophosphate Synthase and Evaluation of Their Antitumor Efficacy in Multiple Myeloma, Pancreatic Ductal Adenocarcinoma, and Colorectal Cancer.
J Med Chem. 2023 Dec 14;66(23):15776-15800. doi: 10.1021/acs.jmedchem.3c01271. Epub 2023 Nov 20.
2
The Hydrolysis of Phosphinates and Phosphonates: A Review.
Molecules. 2021 May 11;26(10):2840. doi: 10.3390/molecules26102840.
3
Phosphonate and Bisphosphonate Inhibitors of Farnesyl Pyrophosphate Synthases: A Structure-Guided Perspective.
Front Chem. 2021 Jan 6;8:612728. doi: 10.3389/fchem.2020.612728. eCollection 2020.
4
Structure-Activity Relationships of Butyrophilin 3 Ligands.
ChemMedChem. 2020 Jun 17;15(12):1030-1039. doi: 10.1002/cmdc.202000198. Epub 2020 May 26.
5
Critical Roles for Coiled-Coil Dimers of Butyrophilin 3A1 in the Sensing of Prenyl Pyrophosphates by Human Vγ2Vδ2 T Cells.
J Immunol. 2019 Aug 1;203(3):607-626. doi: 10.4049/jimmunol.1801252. Epub 2019 Jun 21.
6
Discovery of Lipophilic Bisphosphonates That Target Bacterial Cell Wall and Quinone Biosynthesis.
J Med Chem. 2019 Mar 14;62(5):2564-2581. doi: 10.1021/acs.jmedchem.8b01878. Epub 2019 Feb 21.
7
Improving the Efficiency of Vγ9Vδ2 T-Cell Immunotherapy in Cancer.
Front Immunol. 2018 Apr 19;9:800. doi: 10.3389/fimmu.2018.00800. eCollection 2018.
8
Phosphonic acid: preparation and applications.
Beilstein J Org Chem. 2017 Oct 20;13:2186-2213. doi: 10.3762/bjoc.13.219. eCollection 2017.
9
Anti-Tumor Activity and Immunotherapeutic Potential of a Bisphosphonate Prodrug.
Sci Rep. 2017 Jul 20;7(1):5987. doi: 10.1038/s41598-017-05553-0.
10
Anticancer Activity of Polyoxometalate-Bisphosphonate Complexes: Synthesis, Characterization, In Vitro and In Vivo Results.
Inorg Chem. 2017 Jul 3;56(13):7558-7565. doi: 10.1021/acs.inorgchem.7b01114. Epub 2017 Jun 20.
本文引用的文献
1
Lipophilic bisphosphonates as dual farnesyl/geranylgeranyl diphosphate synthase inhibitors: an X-ray and NMR investigation.
J Am Chem Soc. 2009 Apr 15;131(14):5153-62. doi: 10.1021/ja808285e.
2
A rapid crosstalk of human gammadelta T cells and monocytes drives the acute inflammation in bacterial infections.
PLoS Pathog. 2009 Feb;5(2):e1000308. doi: 10.1371/journal.ppat.1000308. Epub 2009 Feb 20.
3
Endocrine therapy plus zoledronic acid in premenopausal breast cancer.
N Engl J Med. 2009 Feb 12;360(7):679-91. doi: 10.1056/NEJMoa0806285.
4
Peripheral blood monocytes are responsible for gammadelta T cell activation induced by zoledronic acid through accumulation of IPP/DMAPP.
Br J Haematol. 2009 Jan;144(2):245-50. doi: 10.1111/j.1365-2141.2008.07435.x. Epub 2008 Nov 7.
5
Aminobisphosphonates as new weapons for gammadelta T Cell-based immunotherapy of cancer.
Curr Med Chem. 2008;15(12):1147-53. doi: 10.2174/092986708784310468.
6
Pivaloyloxymethyl-modified isoprenoid bisphosphonates display enhanced inhibition of cellular geranylgeranylation.
Bioorg Med Chem. 2008 Apr 1;16(7):3652-60. doi: 10.1016/j.bmc.2008.02.016. Epub 2008 Feb 8.
7
Bisphosphonates: an update on mechanisms of action and how these relate to clinical efficacy.
Ann N Y Acad Sci. 2007 Nov;1117:209-57. doi: 10.1196/annals.1402.089.
8
Activity of sulfonium bisphosphonates on tumor cell lines.
J Med Chem. 2007 Nov 29;50(24):6067-79. doi: 10.1021/jm700991k. Epub 2007 Oct 27.
9
Targeting human {gamma}delta} T cells with zoledronate and interleukin-2 for immunotherapy of hormone-refractory prostate cancer.
Cancer Res. 2007 Aug 1;67(15):7450-7. doi: 10.1158/0008-5472.CAN-07-0199.
10
Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases.
Proc Natl Acad Sci U S A. 2007 Jun 12;104(24):10022-7. doi: 10.1073/pnas.0702254104. Epub 2007 May 29.
Zotero 插件