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{{Short description|Family of derivatives of xanthene used as dyes, indicators and fluorescent tracers}}
[[Image:rhodamine B.png|thumb|right|Rhodamine B]]▼
{{distinguish|rhodanine}}
[[Image:rhodamine 6G.png|thumb|right|Rhodamine 6G]]
▲[[Image:rhodamineRhodamine Bskeleton.pngsvg|thumb|right|Rhodamine Bcore structure]]
'''Rhodamine''' ([[IPA chart for English|IPA]]: [{{IPA|ˌrəʊdəmiːn}}]) is a family of related chemical compounds, [[fluorone dye]]s. Examples are '''Rhodamine 6G''' and '''Rhodamine B'''. They are used as a [[dye]] and as a [[dye laser]] [[gain medium]]. It is often used as a [[tracer dye]] within water to determine the rate and direction of flow and transport. Rhodamine dyes [[fluorescence|fluoresce]] and can thus be measured easily and inexpensively with instruments called [[fluorimeter]]s. Rhodamine dyes are used extensively in biotechnology applications such as [[Fluorescence microscope|fluorescence microscopy]], [[flow cytometry]] and [[ELISA]]
[[File:Rodamiini lahustumine veeklaasis.jpg|thumb|Rhodamine in water]]
'''Rhodamine''' {{IPAc-en|ˈ|r|oʊ|d|əm|iː|n}} is a family of related dyes, a subset of the [[triarylmethane dye]]s. They are derivatives of [[xanthene]]. Important members of the rhodamine family are [[rhodamine 6G]], [[rhodamine 123]], and [[rhodamine B]]. They are mainly used to dye paper and inks, but they lack the [[lightfastness]] for fabric dyeing.<ref name=Ull>{{Ullmann's | last1 = Gessner | first1 = Thomas | last2 = Mayer | first2 = Udo | title = Triarylmethane and Diarylmethane Dyes | year = 2000 | doi = 10.1002/14356007.a27_179}}</ref>
 
==Use==
Rhodamine dyes are generally [[toxic]], and are soluble in water, methanol, and ethanol.
Aside from their major applications, they are often used as a [[tracer dye]], e.g. to determine the rate and direction of flow and transport of water. Rhodamine dyes [[fluorescence|fluoresce]] and can thus be detected using [[Fluorometer]]s. Rhodamine dyes are used extensively in biotechnology applications such as [[Fluorescence microscope|fluorescence microscopy]], [[flow cytometry]], [[fluorescence correlation spectroscopy]] and [[ELISA]].<ref>{{Cite journal |last1=Zehentbauer |first1=Florian M. |last2=Moretto |first2=Claudia |last3=Stephen |first3=Ryan |last4=Thevar |first4=Thangavel |last5=Gilchrist |first5=John R. |last6=Pokrajac |first6=Dubravka |last7=Richard |first7=Katherine L. |last8=Kiefer |first8=Johannes |date=2014-03-05 |title=Fluorescence spectroscopy of Rhodamine 6G: Concentration and solvent effects |url=https://www.sciencedirect.com/science/article/pii/S1386142513012195 |journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy |volume=121 |pages=147–151 |doi=10.1016/j.saa.2013.10.062 |pmid=24239710 |bibcode=2014AcSpA.121..147Z |issn=1386-1425}}</ref> Rhodamine 123 is used in biochemistry to inhibit [[mitochondrion]] function. Rhodamine 123 appears to bind to the mitochondrial membranes and inhibit transport processes, especially the [[electron transport chain]], thus slowing down [[cellular respiration]]. It is a substrate of [[P-glycoprotein]] (Pgp), which is usually overexpressed in cancer cells. Recent reports indicate that rhodamine 123 may also be a substrate of multidrug resistance-associated protein (MRP), or more specifically, [[MRP1]].<ref>{{Cite journal |last1=Johnson |first1=L V |last2=Walsh |first2=M L |last3=Chen |first3=L B |date=February 1980 |title=Localization of mitochondria in living cells with rhodamine 123. |journal=Proceedings of the National Academy of Sciences |language=en |volume=77 |issue=2 |pages=990–994 |doi=10.1073/pnas.77.2.990 |doi-access=free |issn=0027-8424 |pmc=348409 |pmid=6965798|bibcode=1980PNAS...77..990J }}</ref>
 
In addition to their major applications, rhodamines are used in [[dye laser]] as [[Active laser medium|gain media]].<ref>[[F. P. Schäfer]] (Ed.), ''Dye Lasers'', 3rd Ed. (Springer-Verlag, Berlin, 1990).</ref><ref>[[F. J. Duarte]] and L. W. Hillman (Eds.), ''Dye Laser Principles'' (Academic, New York, 1990).</ref>
==Rhodamine B==
[[Chemical formula|Molecular Formula]]: [[Carbon|C]]<sub>28</sub>[[Hydrogen|H]]<sub>31</sub>[[Nitrogen|N]]<sub>2</sub>[[Oxygen|O]]<sub>3</sub>[[Chlorine|Cl]]
 
==Other derivatives==
[[Molecular Weight]]: 479.02 [[gram]]s per [[Mole (unit)|mole]]
There are many rhodamine derivatives used for imaging purposes, for example Carboxytetramethylrhodamine (TAMRA),<ref>{{Cite journal |last1=Hendrickson |first1=W. A. |last2=Ward |first2=K. B. |date=1975-10-27 |title=Atomic models for the tetramethylpolypeptide rhodaminebackbones derivativesof TRITCmyohemerythrin and TAMRA,hemerythrin |url=https://pubmed.ncbi.nlm.nih.gov/5 |journal=Biochemical and Biophysical Research Communications |volume=66 |issue=4 |pages=1349–1356 |doi=10.1016/0006-291x(75)90508-2 |issn=1090-2104 |pmid=5}}</ref> tetramethylrhodamine (TMR) and its isothiocyanate derivative (TRITC) and [[sulforhodamine 101]] (and its sulfonyl chloride form [[Texas Red]]) and Rhodamine Red. TRITC is the base rhodamine molecule functionalized with an [[isothiocyanate]] group ('''-N−N=C=S'''), replacing a [[hydrogen]] atom on the bottom ring of the structure. This derivative is reactive towards [[amine]] groups on proteins inside cells. A [[succinimidyl-ester]] functional group attached to the rhodamine core, creating NHS-rhodamine, forms another common amine-reactive derivative. ▼
 
Other derivatives of rhodamine include newer fluorophores such as [[Alexa (fluor)|Alexa 546, Alexa 555633]], [[DyLight Fluor|DyLight 550 and AlexaDyLight 633]], [[HiLyte andfluor 555 HiLyte 594]], [[DyLightJanelia Fluor|DyLightDyes 549JF549 and JF669]], have been tailored for various chemical and biological applications where higher [[Photobleaching|photostability]], increased brightness, different spectral characteristics, or different attachment groups are needed.▼
[[CAS registry number|CAS Number]]: 81-88-9
 
Substituents of the [[xanthene]] core are influencing the properties of the [[xanthene]] dyes by both electronic and steric effects. Specifically designed [[Substituent|substituents]] also allows xanthenes to bear specific functions activatable upon excitation by [[visible light]], e.g. they could act as [[photoremovable protecting group]] for [[Carboxylate|carboxylates]] and [[Halide|halides]],<ref>{{Cite journal |last1=Šebej |first1=Peter |last2=Wintner |first2=Jürgen |last3=Müller |first3=Pavel |last4=Slanina |first4=Tomáš |last5=Al Anshori |first5=Jamaludin |last6=Antony |first6=Lovely Angel Panamparambil |last7=Klán |first7=Petr |last8=Wirz |first8=Jakob |date=2013-03-01 |title=Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ~520 nm |url=https://pubs.acs.org/doi/10.1021/jo301455n |journal=The Journal of Organic Chemistry |language=en |volume=78 |issue=5 |pages=1833–1843 |doi=10.1021/jo301455n |pmid=22827158 |issn=0022-3263}}</ref> [[carbon monoxide]] (thus being a photo[[Carbon monoxide-releasing molecules|CORM]]),<ref>{{Cite journal |last1=Antony |first1=Lovely Angel Panamparambil |last2=Slanina |first2=Tomáš |last3=Šebej |first3=Peter |last4=Šolomek |first4=Tomáš |last5=Klán |first5=Petr |date=2013-09-06 |title=Fluorescein Analogue Xanthene-9-Carboxylic Acid: A Transition-Metal-Free CO Releasing Molecule Activated by Green Light |url=https://pubs.acs.org/doi/10.1021/ol4021089 |journal=Organic Letters |language=en |volume=15 |issue=17 |pages=4552–4555 |doi=10.1021/ol4021089 |pmid=23957602 |issn=1523-7060}}</ref> or added as a secondary functionality of fluorescent dyes, e.g. fluorescent [[PH indicator|pH indicators]].
[[Simplified molecular input line entry specification|SMILES]] structure: {{SMILES|S=[Cl-].CCN(CC)c1ccc2c(OC3=CC(C=CC3=C2c4ccccc4C(O)=O)=[N+](CC)CC)c1}}
 
== References ==
Rhodamine B is used in biology as a [[staining (biology)|staining]] fluorescent dye, sometimes in combination with [[auramine O]], as the [[auramine-rhodamine stain]] to demonstrate [[acid-fast]] organisms, notably ''[[Mycobacterium]]''.
{{reflist}}
 
Rhodamine B is tunable around 610 nm when used as a [[Dye laser|laser dye]].
 
Rhodamine B is also called '''Rhodamine 610''', '''Basic Violet 10''', or '''C.I. 45170'''.
 
==Rhodamine 6G==
[[Image:Coherent 899 dye laser.jpg|thumb|right|A Rhodamine 6G-based dye laser. The dye solution is the orange fluid in the tubes]]
Molecular Formula: C<sub>28</sub>H<sub>31</sub>N<sub>2</sub>O<sub>3</sub>Cl
 
Molecular Weight: 479.02 g/mol
 
CAS Number: 989-38-8
 
[[Simplified molecular input line entry specification|SMILES]] structure: {{SMILES|S=[Cl-].CCNc1cc2OC3=CC(=[NH+]CC)C(=CC3=C(c2cc1C)c4ccccc4C(=O)OCC)C}}
 
Rhodamine 6G is often used as a [[Dye laser|laser dye]], and is pumped by the 2nd (532 nm) harmonic from a [[Nd:YAG laser]]. The dye has a remarkably high [[Photobleaching|photostability]], high [[quantum yield]], low cost, and its lasing range has close proximity to its absorption maximum (approximately 530 nm). The lasing range of the dye is 555 to 585 nm with a maximum at 566 nm.
 
Rhodamine 6G is also called '''Rhodamine 590''', '''R6G''', '''Basic Rhodamine Yellow ''', or '''C.I. 45160'''.
 
==Rhodamine 123==
The laser dye rhodamine 123 is also used in biochemistry to inhibit [[mitochondrion]] function. Rhodamine 123 seems to bind to the mitochondrion membranes and inhibit transport processes, especially the electron transport chain, thus slowing down [[inner respiration]]. It is a substrate of [[P-glycoprotein]] (Pgp), which is usually overexpressed in cancer cells. Recent reports indicate that rhodamine 123 may be also a substrate of multidrug resistance-associated protein (MRP), or more specifically, MRP1.
 
==Other Rhodamine Derivatives==
▲There are many rhodamine derivatives used for imaging purposes, for example the tetramethyl rhodamine derivatives TRITC and TAMRA, sulforhodamine 101 (and its sulfonyl chloride form Texas Red) and Rhodamine Red. TRITC is the base rhodamine molecule functionalized with an [[isothiocyanate]] group ('''-N=C=S'''), replacing a [[hydrogen]] atom on the bottom ring of the structure. This derivative is reactive towards [[amine]] groups on proteins inside cells. A [[succinimidyl-ester]] functional group attached to the rhodamine core, creating NHS-rhodamine, forms another common amine-reactive derivative.
 
▲Other derivatives of rhodamine include newer fluorophores such as [[Alexa (fluor)|Alexa 546, Alexa 555, and Alexa 633]] and [[DyLight Fluor|DyLight 549]], have been tailored for various chemical and biological applications where higher [[Photobleaching|photostability]], increased brightness, different spectral characteristics, or different attachment groups are needed.
 
==External links==
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*Berlier et al. 2003 J. Histochem Cytochem refers to Alexa 633 as a rhodamine derivative.
 
[[Category:FluoroneRhodamine dyes|*]]
[[Category:Rhodamine dyes]]▼
[[Category:Staining dyes]]
▲[[Category:RhodamineLaser dyesgain media]]
[[Category:Fluorescent dyes]]
[[Category:Laser gain media]]
 
{{organic-compound-stub}}
 
[[de:Rhodamine]]
[[pl:Rodamina]]
[[pt:Rodamina]]
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