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Latest revision as of 13:37, 11 April 2022 edit undo84.56.109.91 (talk) →Measure of viability: removed the plural-s of dead, added the plural-s to cells |
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|ImageFile=Phloxine.png |
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| verifiedrevid = 396687735 |
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| Reference=<ref></ref> |
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|IUPACName=Disodium 2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3-oxospiro-3',6'-diolate |
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| ImageFile=Phloxine.png |
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|OtherNames=Cyanosin; Cyanosine; Eosine bluish; Eosine Blue; Cyanosin B; Eosin Blue; Phloxine P; Phloxin B; Eosine I Bluish; Acid red 92; C.I. 45410; D & C Red no. 28 |
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| PIN=Disodium 2′,4′,5′,7′-tetrabromo-4,5,6,7-tetrachloro-3-oxo-3''H''-spirobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) |
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| OtherNames=Cyanosin; Cyanosine; Eosine bluish; Eosine Blue; Cyanosin B; Eosin Blue; Phloxine P; Phloxin B; Eosine I Bluish; Acid red 92; C.I. 45410; D & C Red no. 28 |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=18472-87-2 |
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| CASNo=18472-87-2 |
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| PubChem=6433718 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1=C2C(=C(C(=C1Br))Br)OC3=C(C(=C(C=C3C24C5=C(C(=C(C(=C5Cl)Cl)Cl)Cl)C(=O)O4)Br))Br.. |
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| UNII = 767IP0Y5NH |
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| PubChem=6433718 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 87192 |
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| SMILES=C1=C2C(=C(C(=C1Br))Br)OC3=C(C(=C(C=C3C24C5=C(C(=C(C(=C5Cl)Cl)Cl)Cl)C(=O)O4)Br))Br.. |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=20|H=2|Br=4|Cl=4|Na=2|O=5 |
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| C=20 | H=2 | Br=4 | Cl=4 | Na=2 | O=5 |
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| Appearance=Red to brown powder |
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| Appearance=Red to brown powder |
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| Solubility=Soluble |
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| Solubility=Soluble |
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|Section3={{Chembox Hazards |
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'''Phloxine B''' (commonly known simply as '''phloxine''') is a ] red ] used for coloring ]s and ] in the ]<ref name = "FDA">{{cite book|last1=Food and Drug Administration|title=The Code of Federal Regulations of the United States of America, Title 21, Part 74.1328|date=2001|page = 296|publisher=U S Government Printing Office|url=https://play.google.com/books/reader?id=ziM6AAAAIAAJ&printsec=frontcover&output=reader&hl=en_GB&pg=GBS.PP1|accessdate=15 April 2016}}</ref> and coloring food in ].<ref>{{cite journal|last1=Kamikura|first1=M|title=Thin Layer Chromatography of Synthetic Dyes (X)|journal=Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)|date=1970|volume=11|issue=4|pages=242–248|doi=10.3358/shokueishi.11.242|doi-access=free}}</ref> It is derived from ], but differs by the presence of four ] atoms at positions 2, 4, 5 and 7 of the ] ring and four ] atoms in the ] ring.<ref>{{cite journal|last1=Duarte|first1=Paulo|last2=Ferreira|first2=Diana P.|last3=Ferreira Machado|first3=Isabel|last4=Filipe|first4=Luis|last5=Ferreira|first5=Vieira|last6=Rodríguez|first6=Hernan B.|last7=San Román|first7=Enrique|title=Phloxine B as a Probe for Entrapment in Microcrystalline Cellulose|journal=Molecules|date=2012|volume=17|issue=2|pages=1602–1616|doi=10.3390/molecules17021602|pmid=22314381|pmc=6268435|doi-access=free}}</ref> It has an ] maximum around 540 nm and an ] maximum around 564 nm.<ref>{{cite journal|last1=Coppeta|first1=J.|last2=Rogers|first2=C.|title=Dual emission laser induced fluorescence for direct planar scalar behavior measurements|journal=Experiments in Fluids|date=1998|volume=25|issue=1|pages=1–15|doi=10.1007/s003480050202|bibcode=1998ExFl...25....1C|s2cid=37649159}}</ref> Apart from industrial use, phloxine B has functions as an ] substance, ] dye and ].<ref name="Rasooly2002">{{cite journal|last1=Rasooly|first1=Avraham|last2=Weisz|first2=Adrian|title=In Vitro Antibacterial Activities of Phloxine B and Other Halogenated Fluoresceins against Methicillin-Resistant Staphylococcus aureus|journal=Antimicrobial Agents and Chemotherapy|date=2002|volume=46|issue=11|pages=3650–3653|doi=10.1128/AAC.46.11.3650-3653.2002|pmid=12384384|pmc=128710}}</ref> For example, it is used in hematoxylin-phloxine-saffron (]) staining to color the ] and ] in shades of red.<ref>{{cite web|last1=Borgerink|first1=Hermina|title=HPS stain|url=http://histonet.utsouthwestern.narkive.com/CdlDznhK/hps-stain|website=Narkive Mailing List Archive|accessdate=18 April 2016}}</ref> |
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== Antimicrobial properties == |
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'''Phloxine B''' (commonly known simply as '''phloxine''') is a red-colored ] that is used in the ] (HPS stain).<ref></ref> It is commonly used to do ] count by ]. |
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=== Lethal dosage levels === |
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In the presence of ], phloxine B has a ] effect on ] strains, such as '']'', '']'', and several ]-resistant '']'' (]) strains.<ref name="Rasooly2005">{{cite journal |last1=Rasooly |first1=Reuven |title=Expanding the bactericidal action of the food color additive phloxine B to gram-negative bacteria |journal=FEMS Immunology & Medical Microbiology |date=August 2005 |volume=45 |issue=2 |pages=239–244 |doi=10.1016/j.femsim.2005.04.004 |pmid=15949926 |doi-access=free }}</ref> At a ] of 25 μM, growth is reduced by 10-fold within 2.5 hours. At concentrations of 50 μM and 100 μM, growth is stopped completely and ] decrease by a factor of 10<sup>4</sup> to 10<sup>5</sup>.<ref name="Rasooly2002"/> For humans, the ] deems phloxine B to be safe up to a daily dosage of 1.25 mg/kg.<ref name = "FDA"/> |
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=== Mechanism of action === |
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==References== |
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Bacteria exposed to phloxine B die from ]. Phloxine B ] in water to become a ] ] that ] to positively charged ]s {{citation needed|date=January 2019}}. When phloxine B is subjected to light, occurs and ] and ] are formed. These compounds cause irreversible damage to the bacteria, leading to growth arrest and cell death.<ref name="Rasooly2005"/> ] are phloxine B-resistant due to the outer ] that surrounds them. This ]-coated ] creates a permeability barrier that prevents efficient uptake of the compound. Addition of ], which is known to strip the ]s and increase ],<ref>{{cite journal |last1=Leive |first1=Loretta |last2=Kollin |first2=Virginia |title=Controlling EDTA treatment to produce permeable escherichia coli with normal metabolic processes |journal=Biochemical and Biophysical Research Communications |date=July 1967 |volume=28 |issue=2 |pages=229–236 |doi=10.1016/0006-291x(67)90434-2 |pmid=4166571 }}</ref> removes the phloxine B resistance and allows gram-negative bacteria to be killed as well. |
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== Measure of viability == |
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{{further|Viability assay}} |
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Phloxine B can be used to stain dead cells of several ]s, including '']'' and '']''. When ] in yeast ], the dye is unable to entere cell because of their membranes. Dead yeast cells lose membrane integrity, so phloxine B can enter and stain the intracellular cytosolic compounds. Therefore, staining is a measure of cell death. |
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In cell counting assays, the number of fluorescent (i.e. dead) cells observed through a ] can be compared to the total number of cells to give a measure of mortality.<ref name="Noda2008">{{cite book |doi=10.1016/S0076-6879(08)03202-3 |chapter=Chapter 2 Viability Assays to Monitor Yeast Autophagy |title=Autophagy: Lower Eukaryotes and Non-Mammalian Systems, Part A |series=Methods in Enzymology |year=2008 |last1=Noda |first1=Takeshi |volume=451 |pages=27–32 |pmid=19185710 |isbn=9780123745484 }}</ref> The same principle can be applied at higher throughput by fluorescence-activated ] (]), where all phloxine B-stained cells in a sample are counted.<ref>{{cite journal |last1=Guérin |first1=Renée |last2=Beauregard |first2=Pascale B. |last3=Leroux |first3=Alexandre |last4=Rokeach |first4=Luis A. |title=Calnexin Regulates Apoptosis Induced by Inositol Starvation in Fission Yeast |journal=PLOS ONE |date=16 July 2009 |volume=4 |issue=7 |pages=e6244 |doi=10.1371/journal.pone.0006244 |pmid=19606215 |pmc=2705804 |bibcode=2009PLoSO...4.6244G |doi-access=free }}</ref> |
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==References== |
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