SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc

Abstract

A reversible, reaction-based sensor for biological mobile zinc was designed, prepared, and characterized. The sensing mechanism of this probe is based on the zinc-induced, ring-opening reaction of spirobenzopyran to give a cyanine fluorophore that emits in the deep-red region of the electromagnetic spectrum. This probe is not activated by protons and operates efficiently in aqueous solution at pH 7 and high ionic strength. The mechanism of this reaction was studied by using a combination of kinetics experiments and DFT calculations. The biocompatibility of the probe was demonstrated in live HeLa cells.

Spiropyran‐Based Nanocarrier: A New Zn2+‐Responsive Delivery System with Real‐Time Intracellular Sensing Capabilities

“…Addition of excess Zn 2+ to SpN gave rise to strong absorbance ( λ max ∼550 nm) and fluorescence ( λ ex =532 nm, λ em max =∼660 nm) as shown in Figures B, C, respectively. This is consistent with the switching of spiropyran 1 from the colorless SP isomer to a more colored and fluorescent MC‐Zn 2+ complex . Fluorescence of SpN treated with varying concentrations of Zn 2+ (0–125 μ m ) was recorded to determine the detection limit.…”

“…Exposure of the spiropyran‐based nanocarrier to Zn 2+ isomerizes the component spiropyran (SP) to its ring‐opened merocyanine isomer (MC),, with an associated change in polarity and geometry. We envisioned that this would result in an overall size change of the nanocarrier to release the encapsulated payload.…”

Mechanism of Evolution of Koneramine Complexes from One‐Pot Reactions: Snapshots of Intermediates Offer Facile Routes to New Dipicolylamines

“…Furthermore, bis(pyridin‐2‐ylmethyl)amine (dipicolylamine, dpa) based compounds are well known for their applications as biological zinc sensors such as Zinpyr and ZnAF introduced by Lippard and co‐workers (Figure ) . Anslyn and co‐workers employed dpa‐based compounds in dynamic multicomponent covalent assemblies that are useful as chirality sensing agents .…”

Microstructured Optical Fiber-based Biosensors: Reversible and Nanoliter-Scale Measurement of Zinc Ions

“…The holes also act as micro sample chamber to allow nanoscale sampling 20 , a real advance in biological sensing. sensing mechanism depicted here was modeled by Rivera-Fuentes et al 24 on a similar analog using density functional theory calculations. 24 The ring-opened isomer is induced by binding to Zn 2+ or by exposure to UV light (λem = 320 -350 nm), while the ring-closed isomer is induced by exposure to white light (broad spectrum).…”

“…sensing mechanism depicted here was modeled by Rivera-Fuentes et al 24 on a similar analog using density functional theory calculations. 24 The ring-opened isomer is induced by binding to Zn 2+ or by exposure to UV light (λem = 320 -350 nm), while the ring-closed isomer is induced by exposure to white light (broad spectrum). Samples of the above solutions were then placed on a glass microscope slide, initial fluorescence was measured by irradiating with the 532 nm laser using a Typhoon imager, and aqueous zinc chloride (100 μM) was added to each, the droplets were again irradiated (532 nm), and the resulting fluorescence of the complexed ring opened merocynine isomer measured, see was obtained after the droplets had been air-dried for 18 h.…”