دورية أكاديمية
Elucidating and Optimizing the Photochemical Mechanism of Coumarin-Caged Tertiary Amines.
العنوان: | Elucidating and Optimizing the Photochemical Mechanism of Coumarin-Caged Tertiary Amines. |
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المؤلفون: | Banala S; Janelia Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States., Jin XT; Department of Translational Neuroscience, Wake Forest University School of Medicine, Winston-Salem, North Carolina 27101, United States., Dilan TL; Janelia Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States., Sheu SH; Janelia Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States., Clapham DE; Janelia Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States., Drenan RM; Department of Translational Neuroscience, Wake Forest University School of Medicine, Winston-Salem, North Carolina 27101, United States., Lavis LD; Janelia Research Campus, Howard Hughes Medical Institute, Ashburn, Virginia 20147, United States. |
المصدر: | Journal of the American Chemical Society [J Am Chem Soc] 2024 Jul 31; Vol. 146 (30), pp. 20627-20635. Date of Electronic Publication: 2024 Jul 18. |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 7503056 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5126 (Electronic) Linking ISSN: 00027863 NLM ISO Abbreviation: J Am Chem Soc Subsets: MEDLINE |
أسماء مطبوعة: | Publication: Washington, DC : American Chemical Society Original Publication: Easton, Pa. [etc.] |
مواضيع طبية MeSH: | Coumarins*/chemistry , Amines*/chemistry , Photochemical Processes*, Molecular Structure ; Photolysis |
مستخلص: | Photoactivatable or "caged" pharmacological agents combine the high spatiotemporal specificity of light application with the molecular specificity of drugs. A key factor in all optopharmacology experiments is the mechanism of uncaging, which dictates the photochemical quantum yield and determines the byproducts produced by the light-driven chemical reaction. In previous work, we demonstrated that coumarin-based photolabile groups could be used to cage tertiary amine drugs as quaternary ammonium salts. Although stable, water-soluble, and useful for experiments in brain tissue, these first-generation compounds exhibit relatively low uncaging quantum yield (Φ |
References: | J Am Chem Soc. 2015 Mar 11;137(9):3402-10. (PMID: 25702699) Org Lett. 2017 Jul 7;19(13):3588-3591. (PMID: 28631486) Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8446-76. (PMID: 22829531) Nat Methods. 2015 Mar;12(3):244-50, 3 p following 250. (PMID: 25599551) Angew Chem Int Ed Engl. 2005 Feb 11;44(8):1195-8. (PMID: 15696594) Chem Sci. 2017 Oct 31;9(2):387-391. (PMID: 29629108) Bioorg Med Chem Lett. 2004 Sep 6;14(17):4585-9. (PMID: 15357997) Sci Data. 2017 Mar 28;4:170033. (PMID: 28350380) J Org Chem. 2002 Feb 8;67(3):703-10. (PMID: 11856009) J Org Chem. 2016 Dec 2;81(23):11556-11564. (PMID: 27934458) Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18386-18389. (PMID: 32671906) J Med Chem. 2010 Feb 25;53(4):1546-62. (PMID: 20104850) Chem Rev. 2013 Jan 9;113(1):119-91. (PMID: 23256727) Biochemistry. 2007 May 8;46(18):5479-84. (PMID: 17425336) Adv Exp Med Biol. 1998;449:277-86. (PMID: 10026815) Nat Methods. 2018 May;15(5):347-350. (PMID: 29578537) J Vis Exp. 2019 Jan 25;(143):. (PMID: 30735191) Cell Rep. 2018 May 22;23(8):2236-2244. (PMID: 29791835) Angew Chem Int Ed Engl. 2023 Feb 20;62(9):e202206083. (PMID: 36646644) J Am Chem Soc. 2019 Sep 4;141(35):13734-13738. (PMID: 31430138) Org Lett. 2022 Apr 22;24(15):2804-2808. (PMID: 35394291) Commun Biol. 2019 Nov 29;2:446. (PMID: 31815201) Chembiochem. 2012 Jul 9;13(10):1458-64. (PMID: 22674503) Nat Methods. 2007 Aug;4(8):619-28. (PMID: 17664946) Nature. 2021 Aug;596(7873):553-557. (PMID: 34381215) Proc Natl Acad Sci U S A. 2019 Oct 22;116(43):21427-21437. (PMID: 31601737) Cell Rep. 2023 Oct 31;42(10):113173. (PMID: 37742189) Neuropharmacology. 2010 Sep;59(3):201-7. (PMID: 20566409) Chemistry. 2008;14(5):1621-7. (PMID: 18046693) Acc Chem Res. 2020 Aug 18;53(8):1593-1604. (PMID: 32692149) |
معلومات مُعتمدة: | R21 DA044460 United States DA NIDA NIH HHS; R33 DA044460 United States DA NIDA NIH HHS |
المشرفين على المادة: | 0 (Coumarins) 0 (Amines) A4VZ22K1WT (coumarin) |
تواريخ الأحداث: | Date Created: 20240718 Date Completed: 20240731 Latest Revision: 20240804 |
رمز التحديث: | 20240804 |
مُعرف محوري في PubMed: | PMC11295134 |
DOI: | 10.1021/jacs.4c03092 |
PMID: | 39023430 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1520-5126 |
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DOI: | 10.1021/jacs.4c03092 |