Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Toluidine blue: Difference between pages

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| verifiedrevid = 470611595

| ImageFile=Tolonium chloride.svg

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| IUPACName=(7-amino-8-methylphenothiazin-3-ylidene)-dimethylammonium chloride

| OtherNames=Toluidine blue O

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| UNII = 15XUH0X66N

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| ChEMBL = 1790006

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| ChEBI = 87647

| CASNo_Ref = {{cascite|changed|??}}

| CASNo=92-31-9

| PubChem=7084

| SMILES = [Cl-].CN(C)c1ccc2nc3cc(C)c(N)cc3[s+]c2c1

| MeSHName=Tolonium+chloride

|Section2={{Chembox Properties

| Formula=C₁₅H₁₆N₃S⁺

| MolarMass=270.374 g/mol

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[[File:Poudre et solution TBO.jpg|200px|thumb|Powder and solution of toluidine blue]]

'''Toluidine blue''', also known as '''TBO''' or '''tolonium chloride''' ([[International nonproprietary name|INN]]) is a blue cationic (basic) dye used in [[histology]] (as the '''toluidine blue stain''') and sometimes clinically.

== Test for lignin ==

Toluidine blue [[Solution (chemistry)|solution]] is used in testing for [[lignin]], a complex [[organic compound|organic molecule]] that bonds to [[cellulose]] fibres and strengthens and hardens the [[cell wall]]s in [[plant]]s. A positive toluidine blue test causes the [[Solution (chemistry)|solution]] to turn from blue to blue-green.<ref>{{Cite journal |last=Reitz |first=Nicholas |date=27 January 2021 |title=Lignification of tomato (Solanum lycopersicum) pericarp tissue during blossom-end rot development |url=https://doi.org/10.1016/j.scienta.2020.109759 |journal=Scientia Horticulturae |volume=276|doi=10.1016/j.scienta.2020.109759 |s2cid=225141378 }}</ref> A similar test can be performed with [[phloroglucinol]]-[[HCl]] solution, which turns red.

==Histological uses==

[[Image:Vasculitic neuropathy -n- plastics - high mag.jpg|thumb|right|200px|Toluidine blue stain in a [[vasculitis|vasculitic]] [[peripheral neuropathy]]]]

'''Toluidine blue''' is a basic [[thiazine]] [[metachromatic]] dye with high affinity for acidic tissue components.<ref>{{cite journal |last1=Sridharan |first1=Gokul |last2=Shankar |first2=Akhil A |year=2012 |title=Toluidine blue: A review of its chemistry and clinical utility |journal=J Oral Maxillofac Pathol |volume=16 |issue=2 |pages=251–5 |doi=10.4103/0973-029X.99081 |pmc=3424943 |pmid=22923899 |doi-access=free}}</ref> It stains nucleic acids blue and polysaccharides purple and also increases the sharpness of histology slide images. It is especially useful today for staining [[chromosome]]s in plant or animal tissues, as a replacement for [[Orcein|Aceto-orcein stain]].

Toluidine blue is often used to identify [[mast cell]]s, by virtue of the [[heparin]] in their [[cytoplasmic granule]]s.<ref>{{cite book |title=Histotechnology: A Self-Instructional Text |last1=Carson |first1=Freida L |last2=Hladik |first2=Christa |year=2009 |publisher=[[American Society for Clinical Pathology]] Press |location=Hong Kong |isbn=978-0-89189-581-7 |page=188 |edition=3 }}</ref> It is also used to stain [[proteoglycan]]s and [[glycosaminoglycan]]s in tissues such as cartilage. The strongly acidic macromolecular carbohydrates of mast cells and cartilage are coloured red by the blue dye, a phenomenon called [[metachromasia]].

Alkaline solutions of toluidine blue are commonly used for staining semi-thin (0.5 to 1 μm) sections of resin-embedded tissue. At high pH (about 10) the dye binds to nucleic acids and all proteins. Although everything in the tissue is stained, structural details are clearly visible because of the thinness of the sections. Semi-thin sections are used in conjunction with ultra-thin sections examined by [[electron microscopy]].

Toluidine blue is also commonly used to stain frozen sections (rapid microscopic analysis of a specimen). Because time is of the essence for a frozen section, toluidine blue allows for the frozen section to be stained and reviewed in 10 to 20 seconds.<ref>Sridharan G, Shankar A. "Toluidine blue: A review of its chemistry and clinical utility. J Oral Maxillofac Pathol. 2012 May-Aug; 16(2):251-255</ref> The other staining method for frozen sections (rapid H&E) takes approximately 60 to 90 seconds.

The results depend on the studied organs:<ref>{{Cite web|url=http://www.histalim.com/accueil/activities/our-services/histology/toluidine-blue/|title=Toluidine blue|website=Histalim|url-status=dead|archive-url=https://web.archive.org/web/20180701171603/http://www.histalim.com/accueil/activities/our-services/histology/toluidine-blue/|archive-date=2018-07-01|access-date=2020-03-15}}</ref>

*Mastocytes in purple

*Cartilage in purple

*Mucins in purple/red

*Nuclei in blue

It is used in forensic examination,<ref>{{cite book|last=Olshaker, Jackson and Smock|title=Forensic Emergency Medicine|year=2001|publisher=Lippincott, Williams and Williams|location=Philadelphia|isbn=0781731445|pages=94–97}}</ref> [[renal]] [[pathology]]<ref name="pmid21659728">{{Cite journal |last1=Nicholas |first1=Susanne B |last2=Basgen |first2=John M |last3=Sinha |first3=Satyesh |year=2011 |title=Using stereologic techniques for podocyte counting in the mouse: shifting the paradigm. |journal=Am J Nephrol |volume=33 |issue=Suppl 1 |pages=1–7 |doi=10.1159/000327564 |pmc=3121548 |pmid=21659728}}</ref> and [[neuropathology]].

==Clinical uses==

The dye is sometimes used by surgeons to help highlight areas of [[mucous membrane|mucosal]] [[dysplasia]] (which preferentially take up the dye compared to normal tissue) in [[premalignant]] [[lesion]]s (e.g. [[leukoplakia]]).<ref name="Scully 2000">{{cite journal |last1=Scully |first1=Crispian |last2=Porter |first2=Stephen |date=22 July 2000 |title=ABC of oral health. Swellings and red, white, and pigmented lesions. |journal=BMJ (Clinical Research Ed.) |volume=321 |issue=7255 |pages=225–8 |doi=10.1136/bmj.321.7255.225 |pmc=1118223 |pmid=10903660}}</ref> This can be used to choose the best site of the lesion to [[biopsy]], or during surgery to remove the lesion to decide whether to remove more tissue from the margins of the excision defect or leave it behind.

[[File:SMCpolyhydroxysmall.jpg|thumb|200px|The cluster of cultured [[mast cell]]s was stained with toluidine blue.]]

==See also==

*[[Muscle biopsy]]

*[[Staining]]

*[[Toluidine red]]

==References==

{{reflist}}

==Further reading==

* Carson FL (1997) ''Histotechnology. A Self-Instructional Text.'' 2nd ed. American Society of Clinical Pathologists, Chicago.

* Green FJ (1990) ''The Sigma-Aldrich Handbook of Stains, Dyes and Indicators''. Aldrich Chemical Company, Milwaukee, Wisconsin.

* Horobin RW, Kiernan JA, Eds (2002) ''Conn's Biological Stains. A Handbook of Dyes, Stains and Fluorochromes for Use in Biology and Medicine''. 10th ed. BIOS, Oxford.

* Kiernan JA (2008) ''Histological and Histochemical Methods: Theory and Practice''. 4th ed. Scion, Bloxham, UK.

*{{cite journal |pmc=3424943 |pmid=22923899 |doi=10.4103/0973-029X.99081 |volume=16 |title=Toluidine blue: A review of its chemistry and clinical utility |year=2012 |journal=J Oral Maxillofac Pathol |pages=251–5 |last1=Sridharan |first1=Gokul |last2=Shankar |first2=Akhil A |issue=2 |doi-access=free}}

[[Category:Phenothiazines]]

[[Category:Thiazine dyes]]

[[Category:Chlorides]]