title: A highly selective turn-on fluorescent sensor for glucosamine from amidoquinoline-napthalimide dyads.
abstract: Three amidoquinoline-naphthalimide dyads are designed and synthesized in 67-73% overall yields in 3 steps from commercially available starting materials. Compounds with unsubstituted and nitro naphthalimide (1 and 2) show excellent selective fluorescent responses towards glucosamine with the enhancement of fluorescence quantum yields by 14 folds. The determination of HOMO-LUMO levels by linear sweep voltammetry suggests that the sensing mechanism likely involves the inhibition of photo-induced electron transfer (PET) between the aminoquinoline and naphthalimide moieties by glucosamine. The association constants of 1.55×10(4) and 1.45×10(4)M(-)(1), along with the glucosamine detection limits of 1.06 and 0.29µM are determined for 1 and 2, respectively. The application of 2 as a fluorescent probe for real-time detection of cellular glucosamine at micromolar level in living Caco-2 cells is also demonstrated.
authors.affiliation: Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand.
authors.forename: Kunnigar
authors.initials: K
authors.lastname: Vongnam
authors.affiliation: Program of Pharmaceutical Chemistry and Natural Products, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand.
authors.forename: Chawanphat
authors.initials: C
authors.lastname: Muangnoi
authors.affiliation: Department of Food and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand.
authors.forename: Pornchai
authors.initials: P
authors.lastname: Rojsitthisak
authors.affiliation: Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand; Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Mongkol
authors.initials: M
authors.lastname: Sukwattanasinitt
authors.affiliation: Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand; Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. Electronic address: paitoon.r@chula.ac.th.
authors.forename: Paitoon
authors.initials: P
authors.lastname: Rashatasakhon
mesh_terms: D000634:Aminoquinolines / Q000737:chemistry*; D015374:Biosensing Techniques / Q000379:methods; D018938:Caco-2 Cells; D005456:Fluorescent Dyes / Q000737:chemistry*; D005944:Glucosamine / Q000032:analysis*; D006801:Humans; D053644:Naphthalimides / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods; D013050:Spectrometry, Fluorescence / Q000379:methods
chemical_list: D000634:Aminoquinolines; D005456:Fluorescent Dyes; D053644:Naphthalimides; D005944:Glucosamine
keywords: Aminoquinoline; Cell-imaging; Fluorescence; Glucosamine; Naphthalimide; Sensor