title: Graphene quantum dots decorated with maleimide and zinc tetramaleimido-phthalocyanine: Application in the design of "OFF-ON" fluorescence sensors for biothiols.
abstract: The fabrication of maleimide-derivatized graphene quantum dots (M-GQDs) and zinc phthalocyanine (2) as novel sensor probes for the selective detection of biothiols (cysteine, homocysteine or glutathione) through the rapid and specific Michael addition reaction between biothiols and the maleimide-derivatized probes is presented in this study. GQDs directly functionalized with maleimide units (M-GQDs) were synthesized and deployed for biothiols recognition following the principle of Michael addition. M-GQDs probe was found to be highly sensitive and selective towards biothiols detection in the nanomolar range in aqueous solution and at physiological pH (7.0). On the other hand, non-covalent interaction between pristine GQDs and novel zinc tetramaleimido-derivatized phthalocyanine resulted in the quenching of the pristine GQDs fluorescence emission which was switched back to the "ON" mode by Michael addition mechanism in the presence of biothiols. Tested relevant biomolecules did not interfere in the quantitative recognition of the biothiols. The probes showed to be highly sensitive, specific and selective for biothiols sensing in simulated real samples.
authors.affiliation: Department of Chemistry, Rhodes University, P.O. Box 94, Grahamstown 6140, South Africa.
authors.forename: Ojodomo J
authors.initials: OJ
authors.lastname: Achadu
authors.affiliation: Department of Chemistry, Rhodes University, P.O. Box 94, Grahamstown 6140, South Africa. Electronic address: t.nyokong@ru.ac.za.
authors.forename: Tebello
authors.initials: T
authors.lastname: Nyokong
mesh_terms: D006108:Graphite / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D057230:Limit of Detection; D008301:Maleimides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D045663:Quantum Dots / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000295:instrumentation*; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000737:chemistry; D017967:Zinc Compounds
chemical_list: D007211:Indoles; D054833:Isoindoles; D008301:Maleimides; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D017967:Zinc Compounds; C052159:Zn(II)-phthalocyanine; C043592:maleimide; D006108:Graphite
keywords: Biothiols; Fluorescence quenching; Fluorescence “turn ON”; Graphene quantum dots; Maleimide; Zinc tetramaleimido-phthalocyanine