Page last updated: 2024-12-07

10-n-nonylacridinium orange

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

It seems you're asking about **10-n-nonylacridinium orange**, also known as **NAO**, a fluorescent dye with important applications in research.

Here's a breakdown of NAO and its significance:

**What is NAO?**

* **Structure:** NAO is a cationic dye with an acridinium ring structure, a nitrogen atom, and a long nonyl chain attached to the molecule.
* **Fluorescent Properties:** NAO exhibits fluorescence, meaning it absorbs light at one wavelength and emits light at a longer wavelength. Its fluorescence intensity is sensitive to its environment.
* **Binding Properties:** NAO interacts with and binds to specific structures within cells, primarily:
* **Membrane Phospholipids:** It binds to negatively charged phospholipids in cell membranes, especially those enriched in cardiolipin, a lipid found in mitochondria.
* **DNA/RNA:** NAO can also bind to nucleic acids, but its affinity for phospholipids is higher.

**Why is NAO important for research?**

* **Mitochondrial Function:** Due to its affinity for cardiolipin, NAO has become a valuable tool for studying mitochondria, the energy powerhouses of cells. It allows researchers to:
* **Visualize mitochondria:** NAO's fluorescence can be used to track and image mitochondria within cells.
* **Monitor membrane potential:** Changes in mitochondrial membrane potential can be detected by changes in NAO fluorescence, providing insights into mitochondrial health and function.
* **Study mitochondrial dynamics:** NAO can help visualize changes in mitochondrial size, shape, and movement.
* **Cell Viability and Apoptosis:** NAO's fluorescence can be used to assess cell viability and monitor apoptosis (programmed cell death). It can differentiate between healthy cells with intact membranes and cells undergoing apoptosis, where the membrane potential is disrupted.
* **Other applications:**
* **Membrane Structure:** NAO can be used to study the structure and dynamics of cell membranes, especially in relation to lipid composition and membrane fluidity.
* **Drug Delivery:** NAO can be used to track and monitor the delivery of drugs and other therapeutic agents into cells.

**Important Points:**

* **Fluorescence Spectrophotometry:** NAO is typically used in conjunction with fluorescence spectrophotometry or microscopy to study its fluorescence and its interactions with cellular components.
* **Safety and Handling:** As with many fluorescent dyes, NAO should be handled with care. It can be potentially toxic in high concentrations, and appropriate safety precautions should be taken.

**In summary:** 10-n-nonylacridinium orange (NAO) is a fluorescent dye with a high affinity for negatively charged phospholipids, particularly cardiolipin in mitochondria. It is a valuable tool for studying mitochondrial function, cell viability, membrane dynamics, and drug delivery. Its fluorescence properties make it a versatile probe for research in various fields.

10-N-nonylacridinium orange: stains mitochondria of living HeLa-cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID115086
SCHEMBL ID12215003
MeSH IDM0123525

Synonyms (19)

Synonym
81650-07-9
10-n-nonylacridinium orange
10-n-nonylacridinium orange chloride
acridinium, 3,6-bis(dimethylamino)-10-nonyl-, (2s-(2alpha,5alpha,6beta(s*)))-
NAO ,
3,6-bis(dimethylamino)-10-nonylacridinium
unii-sd9rox569a
acridinium, 3,6-bis(dimethylamino)-10-nonyl-
sd9rox569a ,
78125-98-1
n(10)-nonylacridine orange
nonylacridine orange cation
nonylacridine orange ion
SCHEMBL12215003
10-n-nonyl acridine orange
Q27289149
DTXSID30999372
3,6-bis(dimethylamino)-10-nonylacridin-10-ium
acridine orange 10-nonyl (bromide)

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The data from mitochondria dosed with the lower dye concentration, where it is assumed that all the dye added to the mitochondrial sample was bound to cardiolipin, were used to derive a sensitivity factor relating fluorescence intensity of a mitochondrial event to its cardiolipin content."( Determination of the cardiolipin content of individual mitochondria by capillary electrophoresis with laser-induced fluorescence detection.
Arriaga, EA; Duffy, CF; Fuller, KM, 2002
)
0.31
" Surprisingly, using a single known cytotoxic agent as a positive control for training a multivariate classifier allowed accurate quantification of cytotoxicity for mechanistically unrelated compounds enabling generation of dose-response curves."( A Versatile Cell Death Screening Assay Using Dye-Stained Cells and Multivariate Image Analysis.
Andrews, DW; Collins, TJ; Geng, F; Ylanko, J, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (72)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (6.94)18.7374
1990's19 (26.39)18.2507
2000's28 (38.89)29.6817
2010's15 (20.83)24.3611
2020's5 (6.94)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.66

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.66 (24.57)
Research Supply Index4.33 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.35%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other73 (98.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]