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Alter: pages. Add: s2cid. Formatted dashes. | You can use this bot yourself. Report bugs here. | Suggested by Lightlowemon | Category:Vital stains‎ | via #UCB_Category 2/13
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| ImageName = Neutral red
| ImageName = Neutral red
| IUPACName = 3-Amino-7-dimethylamino-2-methylphenazine hydrochloride
| IUPACName = 3-Amino-7-dimethylamino-2-methylphenazine hydrochloride
| PIN = ''N''<sup>2</sup>,''N''<sup>2</sup>,7-Trimethylphenazine-2,8-diamine
| OtherNames = toluylene red
| OtherNames = toluylene red
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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{{pH indicator|indicator_name=Neutral red|low_pH=6.8|high_pH=8.0|low_pH_color=red|low_pH_text=white|high_pH_color=yellow}}
{{pH indicator|indicator_name=Neutral red|low_pH=6.8|high_pH=8.0|low_pH_color=red|low_pH_text=white|high_pH_color=yellow}}


'''Neutral red''' ('''toluylene red''', '''Basic Red 5''', or '''C.I. 50040''') is a [[phenazine#Aminophenazine|eurhodin]] dye used for [[staining]] in [[histology]]. It stains lysosomes red.<ref>Winckler, J. Vital staining of lysosomes and other cell organelles of the rat with neutral Red. Prog. Histochem. Cytochem. 6, 1–89 (1974).</ref> It is used as a general stain in [[histology]], as a [[counterstain]] in combination with other dyes, and for many staining methods. Together with [[Janus Green B]], it is used to stain [[embryo]]nal tissues and supravital staining of [[blood]]. Can be used for staining [[Golgi apparatus]] in [[cell (biology)|cells]] and [[Nissl granule]]s in [[neuron]]s.
'''Neutral red''' ('''toluylene red''', '''Basic Red 5''', or '''C.I. 50040''') is a [[phenazine#Aminophenazine|eurhodin]] dye used for [[staining]] in [[histology]]. It stains lysosomes red.<ref>{{cite book |last=Winckler |first=Jürgen |date=1973 |title=Vitalfärbung von Lysosomen und anderen Zellorganellen der Ratte mit Neutralrot |trans-title=Vital staining of lysosomes and other cell organelles of the rat with Neutral red |series=Progress in Histochemistry and Cytochemistry |lang=de |volume='''6''' (3) |publisher=Gustav Fischer Verlag |doi=10.1016/S0079-6336(74)80001-X |isbn=3-437-10353-9 |pmid=4142096}}</ref> It is used as a general stain in [[histology]], as a [[counterstain]] in combination with other dyes, and for many staining methods. Together with [[Janus Green B]], it is used to stain [[embryo]]nal tissues and supravital staining of [[blood]]. Can be used for staining [[Golgi apparatus]] in [[cell (biology)|cells]] and [[Nissl granule]]s in [[neuron]]s.


In [[microbiology]], it is used in the [[MacConkey agar]] to differentiate [[bacteria]] for [[lactose]] [[fermentation]].
In [[microbiology]], it is used in the [[MacConkey agar]] to differentiate [[bacteria]] for [[lactose]] [[fermentation]].


[https://medium.com/@GSPChem/neutral-red-8d9c51584fa Neutral red] can be used as a [[vital stain]].<ref name="pmid18600217">{{cite journal | author=Repetto G, del Peso A, Zurita JL | title=Neutral red uptake assay for the estimation of cell viability/cytotoxicity | journal=[[Nature Protocols]] | volume=3 | issue=7 | year=2008 | pages=1125–1131 | doi = 10.1038/nprot.2008.75 | pmid=18600217 | s2cid=24676983 }}</ref> The Neutral Red Cytotoxicity Assay was first developed by Dr. Ellen Borenfreund in 1984. In the Neutral Red Assay live cells incorporate neutral red into their lysosomes. As cells begin to die, their ability to incorporate neutral red diminishes. Thus, loss of neutral red uptake corresponds to loss of cell viability.<ref name=":0">Borenfreund E., Puerner J.A. (1984) A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR90). Journal of Tissue Culture Methods 9(1):7-9.</ref> The neutral red is also used to stain cell cultures for [[microtiter plate|plate]] [[titration]] of [[virus]]es.
[https://medium.com/@GSPChem/neutral-red-8d9c51584fa Neutral red] can be used as a [[vital stain]].<ref>{{cite journal |last1=Repetto |first1=Guillermo |last2=del Peso |first2=Ana |last3=Zurita |first3=Jorge L. |date=2008 |title=Neutral red uptake assay for the estimation of cell viability/cytotoxicity |journal=Nature Protocols |volume=3 |issue=7 |pages=1125–1131 |doi=10.1038/nprot.2008.75 |pmid=18600217}}</ref> The Neutral Red Cytotoxicity Assay was first developed by Dr. Ellen Borenfreund in 1984. In the Neutral Red Assay live cells incorporate neutral red into their lysosomes. As cells begin to die, their ability to incorporate neutral red diminishes. Thus, loss of neutral red uptake corresponds to loss of cell viability.<ref>{{cite journal |last1=Borenfreund |first1=Ellen |last2=Puerner |first2=James A. |date=1984 |title=A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR90) |journal=Journal of Tissue Culture Methods |volume=9 |issue=1 |pages=7–9 |doi=10.1007/BF01666038}}</ref> The neutral red is also used to stain cell cultures for [[microtiter plate|plate]] [[titration]] of [[virus]]es.


Neutral red is added to some [[growth medium|growth media]] for bacterial and [[cell culture]]s. It usually is available as a [[chloride]] salt.
Neutral red is added to some [[growth medium|growth media]] for bacterial and [[cell culture]]s. It usually is available as a [[chloride]] salt.
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==Other references==
==Other references==
*Borenfreund L and JA Puerner. (1985) Toxicity determined in vitro by morphological alterations and neutral red absorption. Journal of Tissue culture methods 9(1):7-9. Toxicology Letters 24(2-3):119-124.
* {{cite journal |last1=Borenfreund |first1=Ellen |last2=Puerner |first2=James A. |date=1985 |title=Toxicity determined in vitro by morphological alterations and neutral red absorption |journal=Toxicology Letters |volume=24 |issue=2–3 |pages=119–124 |doi=10.1016/0378-4274(85)90046-3 |pmid=3983963}}
*Borenfreund E., Babich H., Martín-Alguacil N. (1988) Comparisons of 2 in vitro cytotoxicity assays the Neutral Red (NR) and Tetrazolium MTT Tests. Toxicology In Vitro 2(1):1-6.
* {{cite journal |last1=Borenfreund |first1=E. |last2=Babich |first2=H. |last3=Martin-Alguacil |first3=N. |date=1988 |title=Comparisons of two ''in vitro'' cytotoxicity assays—The neutral red (NR) and tetrazolium MTT tests |journal=Toxicology in Vitro |volume=2 |issue=1 |pages=1–6 |doi=10.1016/0887-2333(88)90030-6 |pmid=20702351}}


{{Stains}}
{{Stains}}

Revision as of 01:46, 22 February 2021

Neutral red
Neutral red
Solid Neutral Red
Neutral Red Aqueous Solution
Names
IUPAC name
3-Amino-7-dimethylamino-2-methylphenazine hydrochloride
Preferred IUPAC name
N2,N2,7-Trimethylphenazine-2,8-diamine
Other names
toluylene red
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.215 Edit this at Wikidata
EC Number
  • 209-035-8
UNII
  • InChI=1S/C15H16N4.ClH/c1-9-6-13-15(8-11(9)16)18-14-7-10(19(2)3)4-5-12(14)17-13;/h4-8H,16H2,1-3H3;1H checkY
    Key: PGSADBUBUOPOJS-UHFFFAOYSA-N checkY
  • InChI=1/C15H16N4.ClH/c1-9-6-13-15(8-11(9)16)18-14-7-10(19(2)3)4-5-12(14)17-13;/h4-8H,16H2,1-3H3;1H
    Key: PGSADBUBUOPOJS-UHFFFAOYAB
  • Cl.n1c3c(nc2c1cc(c(c2)N)C)cc(N(C)C)cc3
Properties
C15H17N4
Molar mass 288.78 g/mol
Melting point 290 °C (554 °F; 563 K)
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H315, H319, H335, H341
P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Neutral red (pH indicator)
below pH 6.8 above pH 8.0
6.8 ⇌ 8.0

Neutral red (toluylene red, Basic Red 5, or C.I. 50040) is a eurhodin dye used for staining in histology. It stains lysosomes red.[1] It is used as a general stain in histology, as a counterstain in combination with other dyes, and for many staining methods. Together with Janus Green B, it is used to stain embryonal tissues and supravital staining of blood. Can be used for staining Golgi apparatus in cells and Nissl granules in neurons.

In microbiology, it is used in the MacConkey agar to differentiate bacteria for lactose fermentation.

Neutral red can be used as a vital stain.[2] The Neutral Red Cytotoxicity Assay was first developed by Dr. Ellen Borenfreund in 1984. In the Neutral Red Assay live cells incorporate neutral red into their lysosomes. As cells begin to die, their ability to incorporate neutral red diminishes. Thus, loss of neutral red uptake corresponds to loss of cell viability.[3] The neutral red is also used to stain cell cultures for plate titration of viruses.

Neutral red is added to some growth media for bacterial and cell cultures. It usually is available as a chloride salt.

Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.

References

  1. ^ Winckler, Jürgen (1973). Vitalfärbung von Lysosomen und anderen Zellorganellen der Ratte mit Neutralrot [Vital staining of lysosomes and other cell organelles of the rat with Neutral red]. Progress in Histochemistry and Cytochemistry (in German). Vol. 6 (3). Gustav Fischer Verlag. doi:10.1016/S0079-6336(74)80001-X. ISBN 3-437-10353-9. PMID 4142096.
  2. ^ Repetto, Guillermo; del Peso, Ana; Zurita, Jorge L. (2008). "Neutral red uptake assay for the estimation of cell viability/cytotoxicity". Nature Protocols. 3 (7): 1125–1131. doi:10.1038/nprot.2008.75. PMID 18600217.
  3. ^ Borenfreund, Ellen; Puerner, James A. (1984). "A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR90)". Journal of Tissue Culture Methods. 9 (1): 7–9. doi:10.1007/BF01666038.

Other references

  • Borenfreund, Ellen; Puerner, James A. (1985). "Toxicity determined in vitro by morphological alterations and neutral red absorption". Toxicology Letters. 24 (2–3): 119–124. doi:10.1016/0378-4274(85)90046-3. PMID 3983963.
  • Borenfreund, E.; Babich, H.; Martin-Alguacil, N. (1988). "Comparisons of two in vitro cytotoxicity assays—The neutral red (NR) and tetrazolium MTT tests". Toxicology in Vitro. 2 (1): 1–6. doi:10.1016/0887-2333(88)90030-6. PMID 20702351.
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