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CXCR4 is involved in various diseases such as inflammation, tumor growth, and cancer metastasis through the interaction with its natural endogenous ligand, chemokine CXCL12. In an effort to develop imaging probes for CXCR4, we developed a novel small molecule CXCR4-targeted PET agent (compound 5) by combining our established benzenesulfonamide scaffold with a labeling component by virtue of click chemistry. 5 shows nanomolar affinity (IC 50 = 6.9 nM) against a known CXCR4 antagonist (TN14003) and inhibits more than 65% chemotaxis at 10 nM in vitro assays. Radiofluorinated compound 5 ([ 18 F]5) demonstrates a competitive cellular uptake against CXCL12 in a dose-dependent manner. Further, microPET images of [ 18 F]5 exhibits preferential accumulation of radioactivity in the lesions of λ-carrageenan-induced paw edema, human head and neck cancer orthotopic xenograft, and metastatic lung cancer of each mouse model.

Titel:	A benzenesulfonamide derivative as a novel PET radioligand for CXCR4.
Autor/in / Beteiligte Person:	Oum, YH ; Shetty, D ; Yoon, Y ; Liang, Z ; Voll, RJ ; Goodman, MM ; Shim, H
Link:	Zum Volltext
Zeitschrift:	Bioorganic & medicinal chemistry, Jg. 28 (2020-01-15), Heft 2, S. 115240
Veröffentlichung:	Oxford : Elsevier Science ; <i>Original Publication</i>: Oxford : New York : Pergamon Press, c1993-, 2020
Medientyp:	academicJournal
ISSN:	1464-3391 (electronic)
DOI:	10.1016/j.bmc.2019.115240
Schlagwort:	Animals Carrageenan administration & dosage Dose-Response Relationship, Drug Edema chemically induced Edema drug therapy Edema metabolism Female Humans Inflammation chemically induced Inflammation drug therapy Inflammation metabolism Injections, Subcutaneous Ligands Male Mice Mice, Nude Molecular Structure Radiopharmaceuticals chemical synthesis Radiopharmaceuticals chemistry Receptors, CXCR4 metabolism Structure-Activity Relationship Sulfonamides chemical synthesis Sulfonamides chemistry Tissue Distribution Benzenesulfonamides Carcinoma, Squamous Cell diagnostic imaging Head and Neck Neoplasms diagnostic imaging Positron-Emission Tomography Radiopharmaceuticals pharmacology Receptors, CXCR4 antagonists & inhibitors Sulfonamides pharmacology
Sonstiges:	Nachgewiesen in: MEDLINE Sprachen: English Publication Type: Journal Article; Research Support, N.I.H., Extramural Language: English [Bioorg Med Chem] 2020 Jan 15; Vol. 28 (2), pp. 115240. <i>Date of Electronic Publication: </i>2019 Nov 30. MeSH Terms: Positron-Emission Tomography* ; Carcinoma, Squamous Cell / diagnostic imaging ; Head and Neck Neoplasms / diagnostic imaging ; Radiopharmaceuticals / pharmacology ; Receptors, CXCR4 / antagonists & inhibitors ; Sulfonamides / *pharmacology ; Animals ; Carrageenan / administration & dosage ; Dose-Response Relationship, Drug ; Edema / chemically induced ; Edema / drug therapy ; Edema / metabolism ; Female ; Humans ; Inflammation / chemically induced ; Inflammation / drug therapy ; Inflammation / metabolism ; Injections, Subcutaneous ; Ligands ; Male ; Mice ; Mice, Nude ; Molecular Structure ; Radiopharmaceuticals / chemical synthesis ; Radiopharmaceuticals / chemistry ; Receptors, CXCR4 / metabolism ; Structure-Activity Relationship ; Sulfonamides / chemical synthesis ; Sulfonamides / chemistry ; Tissue Distribution ; Benzenesulfonamides References: J Med Chem. 2012 Feb 9;55(3):977-94. (PMID: 22085380) ; Bioorg Med Chem. 2012 Feb 15;20(4):1502-10. (PMID: 22264762) ; Theranostics. 2015 Mar 01;5(6):618-30. (PMID: 25825601) ; Mol Imaging. 2014;13:null. (PMID: 25341373) ; Arthritis Rheum. 2010 Nov;62(11):3436-46. (PMID: 20722038) ; Bioorg Med Chem Lett. 2013 Nov 15;23(22):6079-82. (PMID: 24100078) ; Nucl Med Biol. 2018 May;60:37-44. (PMID: 29544122) ; Nature. 1996 Aug 29;382(6594):833-5. (PMID: 8752281) ; J Nucl Med. 2010 Nov;51(11):1796-804. (PMID: 20956475) ; J Nucl Med. 2011 Jun;52(6):986-93. (PMID: 21622896) ; Cancer Res. 2010 May 15;70(10):3935-44. (PMID: 20460522) ; PLoS One. 2012;7(4):e34038. (PMID: 22485156) ; Cancer Res. 2005 Jan 15;65(2):465-72. (PMID: 15695388) ; J Control Release. 2012 Jan 30;157(2):216-23. (PMID: 21964282) ; Bioorg Med Chem. 2009 Feb 15;17(4):1486-93. (PMID: 19188071) ; Immunology. 1999 Sep;98(1):36-41. (PMID: 10469231) ; Mol Imaging Biol. 2013 Dec;15(6):758-67. (PMID: 23636490) ; Science. 2010 Nov 19;330(6007):1066-71. (PMID: 20929726) ; Angew Chem Int Ed Engl. 2003 Jul 21;42(28):3251-3. (PMID: 12876735) ; J Exp Med. 1997 Oct 20;186(8):1383-8. (PMID: 9334378) ; Arthritis Res Ther. 2010;12(5):R188. (PMID: 20939892) ; Molecules. 2019 Apr 24;24(8):null. (PMID: 31022852) ; Cancer Lett. 2014 Sep 28;352(1):36-53. (PMID: 24141062) ; EJNMMI Res. 2016 Dec;6(1):70. (PMID: 27655427) ; Eur J Med Chem. 2017 Oct 20;139:519-530. (PMID: 28826086) ; J Biol Chem. 1998 Jun 26;273(26):15883-6. (PMID: 9632631) ; Biochem Biophys Res Commun. 1998 Dec 30;253(3):877-82. (PMID: 9918823) ; Theranostics. 2013;3(1):47-75. (PMID: 23382786) ; Theranostics. 2013;3(1):40-6. (PMID: 23382785) ; ChemMedChem. 2013 Apr;8(4):622-32. (PMID: 23468189) ; Chembiochem. 2014 Jul 21;15(11):1614-20. (PMID: 24990206) ; Chem Soc Rev. 2012 Aug 7;41(15):5239-61. (PMID: 22743644) ; J Bone Miner Res. 2003 Aug;18(8):1404-18. (PMID: 12929930) ; Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):1925-30. (PMID: 9050881) ; Mol Neurobiol. 2010 Jun;41(2-3):351-5. (PMID: 20405342) ; J Nucl Med. 2011 Nov;52(11):1803-10. (PMID: 22045709) ; Nat Rev Immunol. 2011 Aug 25;11(9):597-606. (PMID: 21866172) ; J Pathol. 2012 Jan;226(2):148-57. (PMID: 21989643) ; Mol Pharm. 2019 May 6;16(5):2106-2117. (PMID: 30883140) ; Cancer Res. 2007 Aug 1;67(15):7518-24. (PMID: 17671223) ; Exp Cell Res. 2011 Mar 10;317(5):575-89. (PMID: 21223965) ; J Immunol. 1998 Feb 1;160(3):1522-31. (PMID: 9570576) ; Nucl Med Biol. 2014 Aug;41(7):552-61. (PMID: 25038987) ; Eur J Pharmacol. 2009 Jun 24;613(1-3):146-54. (PMID: 19285061) ; J Nucl Med. 2016 May;57(5):741-6. (PMID: 26769866) Grant Information: R01 CA165306 United States CA NCI NIH HHS Contributed Indexing: Keywords: C-X-C chemokine receptor type 4 (CXCR4); CXCL12; Head and neck cancer; Inflammation; Metastasis; Molecular imaging probe; Positron emission tomography (PET) Substance Nomenclature: 0 (CXCR4 protein, human) ; 0 (Ligands) ; 0 (Radiopharmaceuticals) ; 0 (Receptors, CXCR4) ; 0 (Sulfonamides) ; 9000-07-1 (Carrageenan) Entry Date(s): Date Created: 20191218 Date Completed: 20210127 Latest Revision: 20231213 Update Code: 20240513 PubMed Central ID: PMC6942325

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A benzenesulfonamide derivative as a novel PET radioligand for CXCR4.