A glycosylation strategy to develop a low toxic naphthalimide fluorescent probe for the detection of Fe³⁺in aqueous medium

Abstract

A glycosylation strategy based on click chemistry was employed to develop a naphthalimide-based Fe fluorescent probe with low cytotoxicity and good water-solubility. The selectivity and sensitivity to Fe of three synthesized naphthalimide-based fluorescent probes follows a Nap-PZ < Nap-OH < Nap-Glc trend, because Nap-PZ was modified with a good water-soluble group. The cytotoxicity follows a Nap-PZ > Nap-OH > Nap-Glc trend, because the exposed toxic group of Nap-PZ was shielded by a good biocompatible group. The detection limit toward Fe ion follows a Nap-PZ (7.40 × 10 M) > Nap-OH (2.73 × 10 M) > Nap-Glc (4.27 × 10 M) trend. Moreover, Nap-Glc could be used to detect Fe in living cells. The fluorescent "off-on" response of Nap-Glc towards Fe could be recognized by the naked eye, and the "off-on" fluorescent mechanism also was demonstrated by theoretical calculations. Therefore, Nap-Glc is a novel glucosyl naphthalimide fluorescent probe for environmental or biological detection of Fe with low cytotoxicity and good water-solubility.

Tuning the fluorescence sensing for Fe3+ ions by using different dipyridyl linkers in pillar-layered metal–organic frameworks

“…9 Thus, developing other approaches for detecting Fe 3+ ions is extremely urgent. To date, a plethora of fluorescent sensors for detecting Fe 3+ , such as organic fluorescent sensors (rhodamine 10 and napthalamide 11 ), polymer-based sensors (NBN-embedded polymers), 12 and nanocomposite-based fluorescent sensors (carbon quantum dots and g-C 3 N 4 nanosheets), 13 have been reported because of their high sensitivity, efficiency, and convenient manipulation. 14 However, their practical applications have been limited due to low water solubility, instability, high toxicity, difficult separation, and slow response towards Fe 3+ ions.…”

Aggregation-induced emission (AIE) from poly(1,4-dihydropyridine)s synthesized by Hantzsch polymerization and their specific detection of Fe2+ ions

“…Furthermore, if the iron concentration is too high in the body, this can cause cardiovascular and liver damage. [9][10][11][12] In organisms, iron ions often exist in the form of Fe 2+ ions and Fe 3+ ions. 13 Therefore, the identification and detection of iron ions has practical significance and aroused the active attention of many scholars.…”

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

“…[4,5,6] Alternatively, from the fluorescent-probe standpoint, owing to the relevancet hat carbohydrate-receptor interactions have on a number of biological processes, [7] ag lycosyl moiety linked to a fluorophore could play as ignificant role as at argeting [8] and internalizing [9] agentf or the probe, sometimes providing less cytotoxic entities. [10] On the other hand,b orondipyrromethene (BODIPY) dyes, for example, A (Scheme 1), [11] have emerged as remarkablef luorophores owingt ot heir outstandingp roperties that include strongU V/Vis absorption profiles, highf luorescenceq uantum yields( f)a nd excellentp hotochemical and thermals tabilities, whichh as led to their use in biomaterialsl abeling, [12] among others. [13] Of particulari nterest to us was that the ligations tep of the fluorophore, for example, A,a nd the glycoligand, for example, B,l eadingt og lycoprobes, for example, C (Scheme 1, approach i), is generallyc arried out as the last synthetic event, sometimes in situ, prior to their submission to the different vis-Scheme1.i) General synthetic approach to glycoprobe C by ligation of a given saccharide B to ag eneric BODIPY dye (A,IUPAC numbering);and ii) proposed sequential glycosylation/deprotection/glycosylation strategy from hydroxymethyl-BODIPY D and glycosyl donors E,leading to BODIPY-saccharide structures C. ualization or detection techniques.…”