Neutral red is a cationic dye that has been used as a biological stain since the late 19th century. It is synthesized by reacting 3-amino-6-dimethylamino-2-methylphenol with nitrous acid. Neutral red is a weak base that can be absorbed by cells and accumulate in lysosomes. It is used as a vital stain to visualize lysosomes and other acidic compartments in living cells. It is also used as a pH indicator. Neutral red is known to have cytotoxic effects on cells, and it has been studied as a potential anticancer agent. Its use as a biological stain is important for understanding cellular processes and for diagnostic purposes.'
neutral red base : A member of the class of phenazines carrying methyl, amino and dimethylamino substituents at positions 2, 3 and 7 respectively. The free base of neutral red, which acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 11106 |
| CHEMBL ID | 278037 |
| CHEBI ID | 86372 |
| SCHEMBL ID | 3193054 |
| Synonym |
|---|
| MLS001179138 , |
| smr000476020 |
| n-(8-amino-7-methyl-2-phenazinyl)-n,n-dimethylamine |
| AE-848/34087042 |
| n(sup 8),n(sup 8),3-trimethyl-2,8-phenazinediamine |
| c.i. basic red 5, free base |
| neutral red base |
| brn 0022518 |
| 2,8-phenazinediamine, n(sup 8),n(sup 8),3-trimethyl- |
| phenazine, 3-amino-7-dimethylamino-2-methyl- |
| 2,8-phenazinediamine, n8,n8,3-trimethyl- |
| n8,n8,3-trimethylphenazine-2,8-diamine |
| VU0419394-1 |
| 8-n,8-n,3-trimethylphenazine-2,8-diamine |
| chebi:86372 , |
| CHEMBL278037 |
| unii-i64iqb89jb |
| 4-25-00-03054 (beilstein handbook reference) |
| 366-13-2 |
| i64iqb89jb , |
| neutral red free base |
| neutral red base [mi] |
| SCHEMBL3193054 |
| (8-amino-7-methyl-phenazin-2-yl)-dimethyl-amine |
| cid_11106 |
| bdbm53017 |
| 3-amino-7-dimethylamino-2-methylphenazine |
| n(8),n(8),3-trimethylphenazine-2,8-diamine |
| DTXSID10190082 |
| neutralrot |
| Q27159113 |
| n2,n2,7-trimethylphenazine-2,8-diamine |
| Role | Description |
|---|---|
| dye | null |
| acid-base indicator | An acid or base which exhibits a colour change on neutralization by the basic or acidic titrant at or near the equivalence point of a titration. |
| two-colour indicator | A colour indicator that possesses a different colour on each side of the transition interval. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| phenazines | Any organonitrogen heterocyclic compound based on a phenazine skeleton and derivatives. |
| tertiary amino compound | A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups. |
| primary amino compound | A compound formally derived from ammonia by replacing one hydrogen atom by an organyl group. |
| aromatic amine | An amino compound in which the amino group is linked directly to an aromatic system. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 50.1187 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 22.3872 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
| WRN | Homo sapiens (human) | Potency | 50.1187 | 0.1683 | 31.2583 | 100.0000 | AID651768 |
| USP1 protein, partial | Homo sapiens (human) | Potency | 35.4813 | 0.0316 | 37.5844 | 354.8130 | AID743255 |
| TDP1 protein | Homo sapiens (human) | Potency | 17.5886 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| apical membrane antigen 1, AMA1 | Plasmodium falciparum 3D7 | Potency | 2.8184 | 0.7079 | 12.1943 | 39.8107 | AID720542 |
| hypothetical protein, conserved | Trypanosoma brucei | Potency | 35.4813 | 0.2239 | 11.2451 | 35.4813 | AID624173 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 23.6088 | 0.3548 | 28.0659 | 89.1251 | AID504847; AID602199; AID602200; AID602201; AID602202 |
| nuclear factor erythroid 2-related factor 2 isoform 2 | Homo sapiens (human) | Potency | 4.6109 | 0.0041 | 9.9848 | 25.9290 | AID504444 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 112.2020 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| transcriptional regulator ERG isoform 3 | Homo sapiens (human) | Potency | 31.6228 | 0.7943 | 21.2757 | 50.1187 | AID624246 |
| flap endonuclease 1 | Homo sapiens (human) | Potency | 7.0795 | 0.1337 | 25.4129 | 89.1251 | AID588795 |
| serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 0.8437 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
| peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Homo sapiens (human) | Potency | 39.8107 | 0.4256 | 12.0591 | 28.1838 | AID504891 |
| DNA polymerase eta isoform 1 | Homo sapiens (human) | Potency | 50.1187 | 0.1000 | 28.9256 | 213.3130 | AID588591 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 6.3096 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
| urokinase-type plasminogen activator precursor | Mus musculus (house mouse) | Potency | 28.1838 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| plasminogen precursor | Mus musculus (house mouse) | Potency | 28.1838 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| urokinase plasminogen activator surface receptor precursor | Mus musculus (house mouse) | Potency | 28.1838 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 3.1623 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| Rap guanine nucleotide exchange factor 3 | Homo sapiens (human) | Potency | 100.0000 | 6.3096 | 60.2008 | 112.2020 | AID720709 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| integrase, partial | Human immunodeficiency virus 1 | IC50 (µMol) | 27.4755 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
| lens epithelium-derived growth factor p75 | Homo sapiens (human) | IC50 (µMol) | 27.4755 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
| Arrestin, beta 1 | Homo sapiens (human) | IC50 (µMol) | 8.8840 | 1.5240 | 4.0160 | 8.8840 | AID588783 |
| Apoptotic peptidase activating factor 1 | Homo sapiens (human) | IC50 (µMol) | 67.0000 | 0.0375 | 18.6232 | 53.2000 | AID588524; AID588538 |
| caspase-9 isoform alpha precursor | Homo sapiens (human) | IC50 (µMol) | 14.5000 | 0.0256 | 16.5070 | 52.8000 | AID588574 |
| caspase-3 isoform a preproprotein | Homo sapiens (human) | IC50 (µMol) | 14.5000 | 0.0256 | 20.3235 | 74.3000 | AID588574 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| POsterior Segregation | Caenorhabditis elegans | EC50 (µMol) | 13.0040 | 2.2010 | 47.1808 | 186.6810 | AID1964 |
| Sodium-dependent noradrenaline transporter | Homo sapiens (human) | EC50 (µMol) | 14.2540 | 0.0820 | 31.0243 | 168.9080 | AID1960 |
| Zinc finger protein mex-5 | Caenorhabditis elegans | EC50 (µMol) | 14.2540 | 0.0820 | 33.5679 | 168.9080 | AID1960 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE) (FATTY-ACID-CoA SYNTHASE) | Mycobacterium tuberculosis H37Rv | AC50 | 33.6100 | 2.7300 | 45.8264 | 98.7200 | AID624273 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID232668 | Ratio of inhibitory concentration against Hepatitis C Viral IRES in HC40 cells to that of HCF cells was determined | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules. |
| AID1073365 | Inhibition of Hepatitis C virus IRES RNA-driven translation | 2014 | Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5 | Hepatitis C virus translation inhibitors targeting the internal ribosomal entry site. |
| AID79769 | Cytotoxic concentration of compound HC40 cells determined by using MTT assay | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules. |
| AID79770 | Anti-Hepatitis C Viral IRES activity of compound by measured as Fluci signal in HC40 cells | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules. |
| AID241636 | Inhibitory concentration against hepatitis C virus internal ribosomal entry site | 2005 | Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1 | Control of hepatitis C: a medicinal chemistry perspective. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 3 (42.86) | 29.6817 |
| 2010's | 3 (42.86) | 24.3611 |
| 2020's | 1 (14.29) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.70) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (28.57%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (71.43%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||