Page last updated: 2024-12-05

1-phenylazo-2-naphthylamine

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

1-phenylazo-2-naphthylamine (Sudan I) is an **azo dye** with the chemical formula C16H13N3.

**Here's why it's important in research:**

* **Biological Staining:** Sudan I is a **lipophilic dye**, meaning it has an affinity for fats and oils. This property makes it useful in **biological research for staining lipids** in tissues and cells.
* **Microscopy:** It's used to visualize fat droplets, cell membranes, and other lipid-rich structures under a microscope.
* **Histological staining:** Sudan I helps researchers differentiate between various tissues based on their lipid content.
* **Chemical Analysis:** Its color-changing properties are useful in chemical analysis, particularly in:
* **Spectrophotometry:** The intensity of Sudan I's color can be measured to quantify the amount of lipids in a sample.
* **Titration:** It can be used as an indicator in titrations involving lipid-based reactions.
* **Model System:** Sudan I is often used as a model system for studying **dye-substrate interactions**, which is relevant in areas like:
* **Drug delivery:** Understanding how dyes interact with biological molecules can help in designing targeted drug delivery systems.
* **Bioimaging:** Sudan I's properties can be used to develop new imaging techniques for studying cellular processes.

**Important Notes:**

* **Toxicity:** Sudan I has been classified as a **possible human carcinogen**, so it should be handled with caution in the lab.
* **Alternative Dyes:** Many alternative dyes are available for lipid staining, with varying degrees of toxicity and specificity.

In conclusion, 1-phenylazo-2-naphthylamine (Sudan I) is a valuable tool in biological and chemical research. Its properties make it useful for staining, analyzing, and understanding lipid-based processes, but its potential toxicity requires careful consideration.

Cross-References

ID SourceID
PubMed CID6824
CHEMBL ID86177
CHEMBL ID1734418
CHEBI ID82554
SCHEMBL ID295204
SCHEMBL ID295205
MeSH IDM0128134

Synonyms (75)

Synonym
CHEMBL86177
chebi:82554 ,
ccris 3193
brn 1842536
zlut rozpoustedlova 5 [czech]
ci solvent yellow 5
hsdb 1041
ci 11380
af yellow no. 2
a.f. yellow no. 2
1-benzene-azo-beta-naphthylamine
zlut maselna ab [czech]
1-(phenylazo)naphthalen-2-amine
ai3-09035
1-phenylazo-2-naphthylamine
nsc 11228
solvent yellow 5
ext d and c yellow no. 9
einecs 201-636-3
azo benzene 1-naphthalene, 2'-amino-
1-benzeneazo-2-naphthylamine
1-(phenylazo)-2-naphthalenamine
1-benzeneazo-.beta.-naphthylamine
85-84-7
a.f. yellow no.2
fd & c yellow 3
grasal yellow
nsc11228
c.i. 11380
2-naphthylamine, 1-(phenylazo)-
jaune ab
c.i. solvent yellow 5
mls002638198 ,
cerisol yellow ab
yellow ab
1-(phenylazo)-2-naphthylamine
dolkwal yellow ab
c.i. food yellow 10
yellow no. 2
fd and c yellow no. 3
nsc-11228
wln: l66j bnunr& cz
2-naphthalenamine, 1-(phenylazo)-
smr001547687
1-phenyldiazenylnaphthalen-2-amine
AKOS004120651
C19552
1-(2-phenyldiazenyl)-2-naphthalenamine
HMS3080K05
zlut rozpoustedlova 5
3vsi4d701x ,
2-naphthalenamine, 1-(2-phenyldiazenyl)-
zlut maselna ab
unii-3vsi4d701x
FT-0608255
ki404
c.i. food yellow 10 [hsdb]
yellow ab [iarc]
1-(phenylazo)-2-naphthylamine [ii]
fd&c yellow no. 3 (delisted)
yellow ab [mi]
ki404 [inci]
SCHEMBL295204
SCHEMBL295205
AKOS016037985
1-phenylazonaphthalen-2-amine
DTXSID0058932
CHEMBL1734418
1-(phenyldiazenyl)-2-naphthalenamine #
KLCDQSGLLRINHY-UHFFFAOYSA-N
(e)-1-(phenyldiazenyl)naphthalen-2-amine
(e)-1-(phenylazo)-2-naphthylamine
Q27156064
1-(phenyldiazenyl)naphthalen-2-amine
Q26841219
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency12.58930.631035.7641100.0000AID504339
acid sphingomyelinaseHomo sapiens (human)Potency89.125114.125424.061339.8107AID504937
Nrf2Homo sapiens (human)Potency3.54810.09208.222223.1093AID624171
glp-1 receptor, partialHomo sapiens (human)Potency11.22020.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency16.46870.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency12.58930.00527.809829.0929AID588855
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency17.78280.707912.194339.8107AID720542
67.9K proteinVaccinia virusPotency3.54810.00018.4406100.0000AID720579
chromobox protein homolog 1Homo sapiens (human)Potency12.58930.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency10.32250.00419.984825.9290AID504444
flap endonuclease 1Homo sapiens (human)Potency89.12510.133725.412989.1251AID588795
gemininHomo sapiens (human)Potency29.09290.004611.374133.4983AID624296
VprHuman immunodeficiency virus 1Potency63.09571.584919.626463.0957AID651644
Glycoprotein hormones alpha chainHomo sapiens (human)Potency28.18384.46688.344810.0000AID624291
TAR DNA-binding protein 43Homo sapiens (human)Potency22.38721.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID167940Tested for carcinogenic activity on breast after oral administration of the compound; - denotes non carcinogenic activity.1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID168112Carcinogenic activity after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID167951Carcinogenic activity on ear duct after oral administration of the compound; - denotes non carcinogenic activity.1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID168101Carcinogenic activity on mixed data after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID167928Carcinogenic activity on all sites after oral administration1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
AID168085Carcinogenic activity on liver after oral administration of the compound1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Computer-assisted structure-activity studies of chemical carcinogens. Aromatic amines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (44.44)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's2 (22.22)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.83

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 Index11.83 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]