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Tytuł:
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New 1,3-Disubstituted Benzo[ h ]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu Multiphoton Sensitization and Imaging Applications.
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Autorzy:
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Di Pietro S; Department of Pharmacy, University of Pisa, Via Bonanno Pisano 6, 56126 Pisa, Italy.
Iacopini D; Chemistry and Industrial Chemistry Department, University of Pisa, Via G. Moruzzi 3, 56126 Pisa, Italy.
Storti B; CNR-NANO NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy.
Nifosì R; CNR-NANO NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy.
Di Bussolo V; Chemistry and Industrial Chemistry Department, University of Pisa, Via G. Moruzzi 3, 56126 Pisa, Italy.
Pineschi M; Department of Pharmacy, University of Pisa, Via Bonanno Pisano 6, 56126 Pisa, Italy.
Moscardini A; CNR-NANO NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy.
Signore G; CNR-NANO NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy.; Fondazione Pisana per la Scienza, Via F. Giovannini 13, 56017 San Giuliano Terme (PI), Italy.
Bizzarri R; CNR-NANO NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy.; Department of Surgical, Medical and Molecular Pathology, and Critical Care medicine, University of Pisa, Via Roma 55, 56126 Pisa, Italy.
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Źródło:
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Molecules (Basel, Switzerland) [Molecules] 2020 Dec 24; Vol. 26 (1). Date of Electronic Publication: 2020 Dec 24.
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Typ publikacji:
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Journal Article
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Język:
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English
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Imprint Name(s):
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Original Publication: Basel, Switzerland : MDPI, c1995-
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MeSH Terms:
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Cyclams/*chemistry
Isoquinolines/*chemistry
Algorithms ; Chemistry Techniques, Synthetic ; Cyclams/chemical synthesis ; Europium ; Isoquinolines/chemical synthesis ; Ligands ; Luminescence ; Luminescent Measurements ; Models, Molecular ; Models, Theoretical ; Molecular Structure ; Photochemical Processes
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References:
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J Am Chem Soc. 2007 Nov 7;129(44):13502-9. (PMID: 17927176)
Biophys J. 2018 May 8;114(9):2212-2220. (PMID: 29742414)
Chem Commun (Camb). 2013 Feb 28;49(17):1723-5. (PMID: 23340669)
Physiol Rev. 2010 Jul;90(3):1103-63. (PMID: 20664080)
J Biomed Opt. 2008 Nov-Dec;13(6):064001. (PMID: 19123648)
Inorg Chem. 2012 Feb 20;51(4):2522-32. (PMID: 22233349)
PLoS One. 2013 Jul 23;8(7):e68868. (PMID: 23894357)
J Chem Inf Model. 2007 May-Jun;47(3):1045-52. (PMID: 17428029)
Chem Soc Rev. 2010 Jan;39(1):189-227. (PMID: 20023849)
J Biomed Nanotechnol. 2009 Dec;5(6):722-9. (PMID: 20201234)
Opt Express. 2012 Jan 2;20(1):403-13. (PMID: 22274364)
J Chem Theory Comput. 2009 Sep 8;5(9):2420-35. (PMID: 26616623)
Chem Rev. 2010 May 12;110(5):2729-55. (PMID: 20151630)
Chem Rev. 2014 Apr 23;114(8):4496-539. (PMID: 24328202)
J Mol Graph. 1996 Feb;14(1):33-8, 27-8. (PMID: 8744570)
Inorg Chem. 2016 Oct 17;55(20):10645-10653. (PMID: 27668968)
Inorg Chem. 2014 Feb 17;53(4):1854-66. (PMID: 24392868)
Phys Chem Chem Phys. 2009 Mar 7;11(9):1346-53. (PMID: 19224035)
Biophys Chem. 2019 Oct;253:106225. (PMID: 31323431)
Nat Methods. 2005 Dec;2(12):932-40. (PMID: 16299478)
Genes Dis. 2015 Sep;2(3):225-239. (PMID: 26448339)
Opt Lett. 1997 Dec 15;22(24):1905-7. (PMID: 18188403)
ACS Chem Biol. 2018 Aug 17;13(8):2082-2093. (PMID: 29878744)
Phys Chem Chem Phys. 2010 Apr 7;12(13):3195-202. (PMID: 20237709)
Chem Soc Rev. 2015 Jul 21;44(14):4723-42. (PMID: 25588358)
Cell. 2017 Sep 21;171(1):34-57. (PMID: 28938122)
Nat Methods. 2011 Sep 29;8(10):811-9. (PMID: 21959136)
Sci Adv. 2016 Jun 10;2(6):e1600265. (PMID: 27386579)
Biophys J. 2019 Feb 5;116(3):477-486. (PMID: 30709620)
Chem Rev. 2005 Aug;105(8):2999-3093. (PMID: 16092826)
J Med Chem. 2004 Dec 16;47(26):6625-37. (PMID: 15588098)
Inorg Chem. 2014 Feb 17;53(4):1824-38. (PMID: 24099579)
Cancer Biol Ther. 2015;16(5):756-63. (PMID: 25880371)
Inorg Chem. 2016 Jul 18;55(14):7020-5. (PMID: 27367598)
J Chem Theory Comput. 2014 Feb 11;10(2):767-77. (PMID: 26580051)
J Am Chem Soc. 2010 Feb 3;132(4):1276-88. (PMID: 20050646)
J Cell Biochem. 2011 Oct;112(10):2729-41. (PMID: 21678481)
J Comput Chem. 2003 Apr 30;24(6):669-81. (PMID: 12666158)
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Grant Information:
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DIAMANTE - Diagnostica Molecolare Innovativa per la scelta terapeutica personalizzata dell'adenocarcinoma pancreatico Regione Toscana
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Contributed Indexing:
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Keywords: benzoisoquinoline; bioprobe; cyclen; europium complex; structured illumination microscopy
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Substance Nomenclature:
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0 (Cyclams)
0 (Isoquinolines)
0 (Ligands)
444W947O8O (Europium)
964584YO2O (cyclen)
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Entry Date(s):
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Date Created: 20201230 Date Completed: 20210908 Latest Revision: 20210908
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Update Code:
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20240105
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PubMed Central ID:
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PMC7795479
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DOI:
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10.3390/molecules26010058
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PMID:
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33374449
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The development of lanthanide-based luminescent probes with a long emission lifetime has the potential to revolutionize imaging-based diagnostic techniques. By a rational design strategy taking advantage of computational predictions, a novel, water-soluble Eu 3+ complex from a cyclen-based ligand bearing 1,3-disubstituted benzo[h]isoquinoline arms was realized. The ligand has been obtained overcoming the lack of reactivity of position 3 of the isoquinoline moiety. Notably, steric hindrance of the heteroaromatic chromophore allowed selective and stoichiometry-controlled insertion of two or three antennas on the cyclen platform without any protection strategy. The complex bears a fourth heptanoic arm for easy conjugation to biomolecules. This new chromophore allowed the sensitization of the metal center either with one or two photons excitation. The suitability as a luminescent bioprobe was validated by imaging BMI1 oncomarker in lung carcinoma cells following an established immunofluorescence approach. The use of a conventional epifluorescence microscope equipped with a linear structured illumination module disclosed a simple and inexpensive way to image confocally Ln-bioprobes by single photon excitation in the 350-400 nm window, where ordinary confocal systems have no excitation sources.
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