Student or educator? Sign up with your school email and get 6 months of Pro free.
CoChat
Sign Up
Cited by 268

The DOI matches its Crossref record; 58 of the 58 references it cites were found in a registry or an index.

Design of Bis-spiropyran Ligands as Dipolar Molecule Receptors and Application to in Vivo Glutathione Fluorescent Probes

Shao, Na, Jin, Jianyu, Wang, Hao, Zheng, Jing, Yang, Ronghua, Chan, Winghong, Abliz, Zeper·2010·Journal of the American Chemical Society
DOI 10.1021/ja908215t
Open this paper in CoChat — free account

Abstract

Despite considerable efforts toward the development of various sophisticated spiropyrans for metal ion sensing, less attention has been paid to organic molecule sensing. One of the major difficulties for detection of organic molecules using a spiropyran is the weak and nonspecific interaction between the spiropyran and the target. Here, we report the synthesis and molecular recognition characterization of two bis-spiropyrans for dipolar molecules and their application to in vivo glutathione (GSH) fluorescent probes. Unlike the mono-spiropyrans, the newly designed bis-spiropyran molecules feature a rigidly maintained molecular cleft and two spiropyran units as binding modules. The molecular recognition is based on multipoint electrostatic interactions and structure complementarity between the opened merocyanine form of the spiropyran and the analyte. It was observed that the spiropyran 1a binds GSH in aqueous solution with high affinity (K = (7.52 +/- 1.83) x 10(4) M(-1)) and shows strong fluorescence emission upon binding. Remarkably, fluorescence output of 1a is not significantly affected by other amino acids and peptides, especially, structurally similar compounds, such as cysteine and homocysteine. Furthermore, fluorescence anisotropy and confocal fluorescent microscopy confirmed that spiropyran 1a is a comparatively good candidate for intracellular delivery and can be accumulated intensively into cells. Thus, 1a can be utilized in vivo as a GSH probe or as a marker to show the level of intracellular GSH.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/ja908215t

Cites

58 of 58 references verified0 citation errors · 0 not checkable

Statistics

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

Cited by

See all 268

Metadata

Authors
Shao, N., Jin, J., Wang, H., Zheng, J., Yang, R., Chan, W., & Abliz, Z.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2009-12-23
Volume
132
Issue
2
Pages
725-736
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja908215t
OpenAlex
W1986319156
Cited by
268
References
58
FWCI
7.98
Type
journal article
Language
en
Open access
closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.