A New Strategy for the Design of Molecular Probes for Investigating Endogenous Nitric Oxide Using an EPR or Fluorescent Technique

Katayama, Yoshiki; Soh, Nobuaki; Maeda, Mizuo

doi:10.1002/1439-7641(20011119)2:11<655::aid-cphc655>3.0.co;2-s

Cited by 35 publications

(3 citation statements)

References 71 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To delineate the spatial and temporal distributions of NO in living systems, bioimaging techniques are found to be the most promising among various NO detection tools. − In comparison to other NO imaging techniques, fluorescence imaging studies have acquired immense attention due to their noninvasive detection and high sensitivity as well as selectivity toward analytes. By considering all these facts, numerous nitric oxide fluorescent probes have been developed to date, which conventionally exploit the specific reactions of this ubiquitous signaling agent with o -phenylenediamine (OPD) − and metal–ligand complexes. , However, in most of cases, fluorescent NO probes suffer from some serious limitations like (a) the very short half-life of NO in the biological milieu (typically in the range of 0.1–10 s), (b) the false positive response to reactive carbonyl species (RCS) (dehydroascorbic acid, methylglyoxal, etc.)…”

Section: Introductionmentioning

confidence: 99%

N-Nitrosation Based Fluorescence Turn-On Nitric Oxide Probe: Kinetic and Cell Imaging Studies

Dutta,

Maiti,

Katarkar

et al. 2023

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

Nitric oxide (NO) is a ubiquitous messenger molecule playing a key role in various physiological and pathological processes. However, producing a selective turn-on fluorescence response to NO is a challenging task due to (a) the very short half-life of NO (typically in the range of 0.1–10 s) in the biological milieu and (b) false positive responses to reactive carbonyl species (RCS) (e.g., dehydroascorbic acid and methylglyoxal etc.) and some other reactive oxygen/nitrogen species (ROS/RNS), especially with o-phenylenediamine (OPD) based fluorosensors. To avoid these limitations, NO sensors should be designed in such a way that they react spontaneously with NO to give turn-on response within the time frame of t 1/2 (typically in the range of 0.1–10 s) of NO and λem in the visible wavelength along with good cell permeability to achieve biocompatibility. With these views in mind, a N-nitrosation based fluorescent sensor, NDAQ, has been developed that is highly selective to NO with ∼27-fold fluorescence enhancement at λem = 542 nm with high sensitivity (LOD = 7 ± 0.4 nM) and shorter response time, eliminating the interference of other reactive species (RCS/ROS/RNS). Furthermore, all the photophysical studies with NDAQ have been performed in 98% aqueous medium at physiological pH, indicating its good stability under physiological conditions. The kinetic assay illustrates the second-order dependency with respect to NO concentration and first-order dependency with respect to NDAQ concentration. The biological studies reveal the successful application of the probe to track both endogenous and exogenous NO in living organisms.

show abstract

Section: Introductionmentioning

confidence: 99%

N-Nitrosation Based Fluorescence Turn-On Nitric Oxide Probe: Kinetic and Cell Imaging Studies

Dutta,

Maiti,

Katarkar

et al. 2023

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

show abstract

“…Therefore, in recent years, the research on the generation and detection of NO has become the focus of attention of scientists. 12−15 Up to now, the NO-sensing methods including colorimetric, 16 electrochemistry, 17 chemiluminescence, 18 electron paramagnetic resonance spectroscopy, 19 and fluorescent probe analysis 5 have been reported to monitor NO. Among them, the fluorescent probes used to track NO in organisms are favored by chemists due to their high sensitivity and good selectivity.…”

Section: ■ Introductionmentioning

confidence: 99%

Bio-orthogonal Toolbox for Monitoring Nitric Oxide in Targeted Organelles of Live Cells and Zebrafishes

et al. 2022

View full text Add to dashboard Cite

Nitric oxide (NO), playing crucial roles as a cellular messenger and as a toxic ROS, is highly related to the physiological and pathological states of living systems. The very wide but very uneven distribution of this radical gas in the inhomogeneous biological microenvironment imposes big challenges for specifically detecting its local level in certain subcellular areas, which calls for a long list of NO probes for each target. In order to simplify the syntheses and designs of these probes, herein it is proposed to construct a versatile NO-sensing toolbox based on a bio-orthogonal concept, i.e., inverse electron demand Diels–Alder click reaction between tetrazine and strained alkyne BCN. On the one hand, rhodamine-o-phenylenediamine as the NO-responsive scaffold is coupled with a tetrazine unit to generate a general probe TMR-Tz-NO, which, to our knowledge, is the first case of the tetrazine-coupled analyte-responsive probe. On the other hand, the BCN moiety is connected to different targeting groups, such as TPP, morpholine, and Ac4ManN, targeting to mitochondria, lysosomes, and membranes, respectively. It works well to use TMR-Tz-NO to match with any targetable BCN counterpart in this toolbox to achieve the imaging of NO in the corresponding subcellular area. For example, through metabolism, Ac4ManN-BCN is effectively taken and grows on the cell membranes. The bio-orthogonal reaction between TMR-Tz-NO and Ac4ManN-BCN makes the NO probe anchored to the membrane surface permanently. The zebrafish experiment revealed that this bio-orthogonal pair can track and image the NO produced during inflammation in vivo.

show abstract

“…Nitric oxide (NO) is an important multifunctional biomolecule involved in a variety of physiological and pathophysiological processes, including regulation of blood vessel modulation, wound healing, and neuronal communication. − Also, it is suggested that chronically elevated levels of NO are involved in the pathogenesis of some human pathological conditions, such as inflammatory bowel diseases, neurodegenerative disorders, and cancer. , One of the physiological functions of NO is to modulate posttranslational modifications (nitrosation and nitration) of proteins via reactive nitrogen species. , Therefore, NO is recognized as a modulator of many proteins. Several methods for monitoring endogenous NO, such as electron paramagnetic resonance spectroscopy and colorimetric, fluorometric, − electrochemical, and chemiluminescence techniques, have been developed to understand the complicated functions of NO in living systems. However, to the best of our knowledge, there are no methods for analyzing the proteins in the environments where NO is produced.…”

mentioning

confidence: 99%

Development of a Nitric Oxide-Responsive Labeling Reagent for Proteome Analysis of Live Cells

et al. 2019

View full text Add to dashboard Cite

Nitric oxide (NO) is a pleiotropic signaling molecule involved in the regulation of diverse physiological and pathophysiological mechanisms in cardiovascular, nervous, and immunological systems. To understand the biological functions of NO in detail, comprehensive characterization of proteins found in high-NO concentration environments is crucial. Herein, we describe the design of NO-responsive protein labeling reagents based on N-alkoxyacyl-o-phenylenediamine as an optimal reactive scaffold. The designed molecules can label proteins in murine macrophage cells in response to endogenously produced NO. The combination of NO-responsive protein labeling and liquid chromatography–tandem mass spectrometry technology allowed the characterization of the proteome under NO-generated conditions. Moreover, we demonstrated that our reagent was able to selectively mark and be used to fluorescently visualize NO-producing cells in a mixed cell culture system.

show abstract

A New Strategy for the Design of Molecular Probes for Investigating Endogenous Nitric Oxide Using an EPR or Fluorescent Technique

Cited by 35 publications

References 71 publications

N-Nitrosation Based Fluorescence Turn-On Nitric Oxide Probe: Kinetic and Cell Imaging Studies

N-Nitrosation Based Fluorescence Turn-On Nitric Oxide Probe: Kinetic and Cell Imaging Studies

Bio-orthogonal Toolbox for Monitoring Nitric Oxide in Targeted Organelles of Live Cells and Zebrafishes

Development of a Nitric Oxide-Responsive Labeling Reagent for Proteome Analysis of Live Cells

Contact Info

Product

Resources

About