Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers
A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplish...
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Published in | ChemMedChem Vol. 15; no. 10; pp. 833 - 838 |
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Language | English |
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19.05.2020
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Abstract | A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D(KLAKLAK)2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers.
A solid start: A microwave‐mediated, multicomponent reaction on solid support gives good yields of complex 3‐substituted isoindolinones. The products displayed significant fluorescence with excellent Stokes shifts. We also demonstrated fast cell penetration of some of these nontoxic compounds and their conjugates with biologically active molecules, showing them to be attractive molecular probes for cell sensing or as carriers for cell‐penetration applications. |
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AbstractList | A modular solid-phase multicomponent reaction for the synthesis of 3-substituted isoindolinone derivatives has been carried out. A mixture of a chiral beta-keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3-substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well-known programed cell death-inducing peptide (D)(KLAKLAK)(2) on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers. Abstract A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D (KLAKLAK) 2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers. A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D(KLAKLAK)2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers. A solid start: A microwave‐mediated, multicomponent reaction on solid support gives good yields of complex 3‐substituted isoindolinones. The products displayed significant fluorescence with excellent Stokes shifts. We also demonstrated fast cell penetration of some of these nontoxic compounds and their conjugates with biologically active molecules, showing them to be attractive molecular probes for cell sensing or as carriers for cell‐penetration applications. A modular solid-phase multicomponent reaction for the synthesis of 3-substituted isoindolinone derivatives has been carried out. A mixture of a chiral β-keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3-substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well-known programed cell death-inducing peptide (KLAKLAK) on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers. A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D(KLAKLAK)2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers. |
Author | Byk, Gerardo Mazir, Alexandra Massarano, Tlalit Lavi, Ronit |
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Cites_doi | 10.1016/j.tetasy.2007.11.014 10.1021/cr100233r 10.3762/bjoc.9.243 10.1016/j.tet.2004.05.111 10.1021/ol047824w 10.1016/j.biomaterials.2011.03.074 10.1016/j.bbamem.2014.04.025 10.1055/s-2006-932498 10.1016/j.cell.2015.05.023 10.1016/j.semcancer.2013.04.001 10.1016/j.dyepig.2013.09.011 10.1111/cei.12248 10.1002/anie.200907320 10.3998/ark.5550190.0012.923 10.2174/1385272821666170817110101 10.1021/cc049962i 10.1016/j.tetasy.2008.11.021 10.1021/op034060b 10.1038/12469 10.1016/S0040-4039(97)00582-0 10.1002/ange.200907320 10.1182/blood.V81.5.1352.1352 10.1046/j.1523-1755.1998.00202.x 10.1016/S0040-4039(00)97526-9 10.2174/092986712801661004 10.1021/jm9509410 10.1021/ja00897a025 10.1021/cc000056p 10.1016/0040-4020(96)00216-5 |
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Keywords | multicomponent reactions staurosporine ASYMMETRIC-SYNTHESIS PROTEIN cell penetrating probe ONE-POT SYNTHESIS PROAPOPTOTIC PEPTIDE CHEMISTRY flow cytometry EFFICIENT |
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Snippet | A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto... A modular solid-phase multicomponent reaction for the synthesis of 3-substituted isoindolinone derivatives has been carried out. A mixture of a chiral... A modular solid-phase multicomponent reaction for the synthesis of 3-substituted isoindolinone derivatives has been carried out. A mixture of a chiral β-keto... Abstract A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral... |
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SubjectTerms | Aldehydes Amides Apoptosis Cell death cell penetrating probe Chemical synthesis Chemistry, Medicinal Drug carriers Drug delivery flow cytometry Fluorescence Life Sciences & Biomedicine Modularity multicomponent reactions Optimization Peptides Pharmacology & Pharmacy Probes Science & Technology Solid phases staurosporine Substitutes |
Title | Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers |
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