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Rose bengal: Difference between revisions

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| verifiedrevid = 412183348 | verifiedrevid = 412183348
| ImageFile = rosebengalskeletal.png | ImageFile = rosebengalskeletal.png
| ImageSize = | ImageSize =
| IUPACName = <small>4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3''H''- spiro-3-one</small> | IUPACName = <small>4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3''H''- spiro-3-one</small>
| OtherNames = C.I. 45440 | OtherNames = C.I. 45440
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo = 11121-48-5 | CASNo = 11121-48-5
| PubChem = | PubChem =
| SMILES = O=C(O1)C2=C(C(Cl)=C(Cl)C(Cl)=C2Cl)C31<br />C4=C(C(I)=C(O)C(I)=C4)OC5=C(I)C(O)=C(I)C=C53 | SMILES = O=C(O1)C2=C(C(Cl)=C(Cl)C(Cl)=C2Cl)C31<br />C4=C(C(I)=C(O)C(I)=C4)OC5=C(I)C(O)=C(I)C=C53
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = | Formula =
| C=20 | H=4| Cl=4 | I=4 | O=5 | C=20 | H=4| Cl=4 | I=4 | O=5
| MolarMass = 973.67&nbsp;g/mol<br>1,017.65&nbsp;g/mol (sodium salt) | MolarMass = 973.67&nbsp;g/mol<br>1,017.65&nbsp;g/mol (sodium salt)
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | Autoignition = }}
}} }}
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Rose Bengal is also used in ] (photothrombotic stroke models) in biomedical research. A bolus of the compound is injected into the venous system. Then the region of interest (e.g., the cerebral cortex) is exposed and illuminated by LASER light of 561&nbsp;nm. A thrombus is formed in the illuminated blood vessels, causing a stroke in the dependent brain tissue.<ref>Salber D, et al. Differential uptake of FET and l-methionine in focal cortical ischemia. Nuclear Medicine and Biology, Volume 33, Issue 8, Pages 1029-1035</ref><ref>Watson BD, Dietrich WD, Busto R, Wachtel MS, Ginsberg MD: Induction of reproducible brain infarction by photochemically initiated thrombosis. Ann Neurol 17:497-504, 1985</ref> Rose Bengal is also used in ] (photothrombotic stroke models) in biomedical research. A bolus of the compound is injected into the venous system. Then the region of interest (e.g., the cerebral cortex) is exposed and illuminated by LASER light of 561&nbsp;nm. A thrombus is formed in the illuminated blood vessels, causing a stroke in the dependent brain tissue.<ref>Salber D, et al. Differential uptake of FET and l-methionine in focal cortical ischemia. Nuclear Medicine and Biology, Volume 33, Issue 8, Pages 1029-1035</ref><ref>Watson BD, Dietrich WD, Busto R, Wachtel MS, Ginsberg MD: Induction of reproducible brain infarction by photochemically initiated thrombosis. Ann Neurol 17:497-504, 1985</ref>


Rose bengal has been used for 50 years to diagnose liver and eye cancer. It has also been used as an insecticide.<ref>http://www.bioone.org/doi/abs/10.1603/0022-0493-93.3.662?journalCode=ecen</ref><ref>http://www.informaworld.com/smpp/content~db=all~content=a713655913</ref>{{Fact|date=May 2008}} Rose bengal has been used for 50 years to diagnose liver and eye cancer. It has also been used as an insecticide.<ref>http://www.bioone.org/doi/abs/10.1603/0022-0493-93.3.662?journalCode=ecen</ref><ref>http://www.informaworld.com/smpp/content~db=all~content=a713655913</ref>{{Citation needed|date=May 2008}}


Rose Bengal is being researched as an agent in creating nano sutures.<ref>Chan BP et al.: Acta Biomater (2008), doi:10.1016/j.actbio.2008.06.007</ref> Wounds are painted on both sides with it and then illuminated with an intense light. This links the tiny collagen fibers together sealing the wound.<ref>O’Neill A.C., Winograd J.M, Zeballos J.M., Johnson T.S., Randolph M.A., Bujold K.E., Kochevar I.E., Redmond R.W.: Lasers in Surgery and Medicine 39:716–722 (2007)</ref><ref>Mulroy L., Kim J., Wu I., Scharper P., Melki S.A., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2000;41:3335–3340</ref><ref>Proano C.E., Mulroy L., Erika Jones E., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2004, 2177-2181.</ref> Healing is faster and the seal reduces chances of infection.<ref>http://www.technologyreview.com/biomedicine/22088/?nlid=1767</ref><ref>http://www.technologyreview.com/video/?vid=246</ref> Rose Bengal is being researched as an agent in creating nano sutures.<ref>Chan BP et al.: Acta Biomater (2008), doi:10.1016/j.actbio.2008.06.007</ref> Wounds are painted on both sides with it and then illuminated with an intense light. This links the tiny collagen fibers together sealing the wound.<ref>O’Neill A.C., Winograd J.M, Zeballos J.M., Johnson T.S., Randolph M.A., Bujold K.E., Kochevar I.E., Redmond R.W.: Lasers in Surgery and Medicine 39:716–722 (2007)</ref><ref>Mulroy L., Kim J., Wu I., Scharper P., Melki S.A., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2000;41:3335–3340</ref><ref>Proano C.E., Mulroy L., Erika Jones E., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2004, 2177-2181.</ref> Healing is faster and the seal reduces chances of infection.<ref>http://www.technologyreview.com/biomedicine/22088/?nlid=1767</ref><ref>http://www.technologyreview.com/video/?vid=246</ref>
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{{DEFAULTSORT:Rose Bengal}}
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Revision as of 23:58, 16 March 2011

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Rose bengal
Names
IUPAC name 4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H- spiro-3-one
Other names C.I. 45440
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.021.813 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • O=C(O1)C2=C(C(Cl)=C(Cl)C(Cl)=C2Cl)C31
    C4=C(C(I)=C(O)C(I)=C4)OC5=C(I)C(O)=C(I)C=C53
Properties
Chemical formula C20H4Cl4I4O5
Molar mass 973.67 g/mol
1,017.65 g/mol (sodium salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Rose Bengal (4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein) is a stain. Its sodium salt is commonly used in eye drops to stain damaged conjunctival and corneal cells and thereby identify damage to the eye. The stain is also used in the preparation of Foraminifera for microscopic analysis, allowing the distinction between forms that were alive or dead at the time of collection.

A form of Rose Bengal is also being studied as a treatment for certain cancers and skin conditions. The cancer formulation of the drug, known as PV-10, is currently undergoing clinical trials for melanoma and breast cancer. The company also has formulated a drug based on Rose Bengal for the treatment of eczema and psoriasis; this drug, PH-10, is currently in clinical trial as well.

Chemical applications

Light microscopy image of the undescribed species of Spinoloricus from Loricifera stained with Rose Bengal.

Rose Bengal is also used in synthetic chemistry to generate singlet oxygen from triplet oxygen. The singlet oxygen can then undergo a variety of useful reactions, particularly cycloadditions with alkenes and similar systems.

Biological applications

Provectus Pharmaceuticals' proprietary drug PV-10 was found to cause an observable response in 60 percent of tumors treated, according to researchers in a phase II melanoma study. Locoregional disease control was observed in 75 percent of patients. Also confirmed was a "bystander effect", previously observed in the phase I trial, whereby untreated lesions responded to treatment as well, potentially due to immune system response. These data were based on the interim results of the first 40 patients treated in an 80 patient study.

Rose Bengal is also used in animal models of ischemic stroke (photothrombotic stroke models) in biomedical research. A bolus of the compound is injected into the venous system. Then the region of interest (e.g., the cerebral cortex) is exposed and illuminated by LASER light of 561 nm. A thrombus is formed in the illuminated blood vessels, causing a stroke in the dependent brain tissue.

Rose bengal has been used for 50 years to diagnose liver and eye cancer. It has also been used as an insecticide.

Rose Bengal is being researched as an agent in creating nano sutures. Wounds are painted on both sides with it and then illuminated with an intense light. This links the tiny collagen fibers together sealing the wound. Healing is faster and the seal reduces chances of infection.

Rose Bengal is used in several microbiological media, including Cooke's Rose Bengal agar, to suppress bacterial growth.

Electronic applications

Rose Bengal demonstrates at least six distinct electronic properties which are otherwise hidden in the molecule. Rose Bengal is a double planar molecule and relative rotation of the planes generate unique electronics. Therefore, Rose Bengal is a suitable candidate for molecular electronics.

References

  1. http://www.medicalnewstoday.com/articles/153024.php
  2. Salber D, et al. Differential uptake of FET and l-methionine in focal cortical ischemia. Nuclear Medicine and Biology, Volume 33, Issue 8, Pages 1029-1035
  3. Watson BD, Dietrich WD, Busto R, Wachtel MS, Ginsberg MD: Induction of reproducible brain infarction by photochemically initiated thrombosis. Ann Neurol 17:497-504, 1985
  4. http://www.bioone.org/doi/abs/10.1603/0022-0493-93.3.662?journalCode=ecen
  5. http://www.informaworld.com/smpp/content~db=all~content=a713655913
  6. Chan BP et al.: Acta Biomater (2008), doi:10.1016/j.actbio.2008.06.007
  7. O’Neill A.C., Winograd J.M, Zeballos J.M., Johnson T.S., Randolph M.A., Bujold K.E., Kochevar I.E., Redmond R.W.: Lasers in Surgery and Medicine 39:716–722 (2007)
  8. Mulroy L., Kim J., Wu I., Scharper P., Melki S.A., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2000;41:3335–3340
  9. Proano C.E., Mulroy L., Erika Jones E., Azar D.A., Redmond R.W., Kochevar I.E.: Invest Ophthalmol Vis Sci. 2004, 2177-2181.
  10. http://www.technologyreview.com/biomedicine/22088/?nlid=1767
  11. http://www.technologyreview.com/video/?vid=246
  12. A new approach to extract multiple distinct conformers and co-existing distinct electronic properties of a single molecule by point-contact method Anirban Bandyopadhyay, Satyajit Sahu, Daisuke Fujita and Yutaka Wakayama, Phys. Chem. Chem. Phys., 2010 view highlights in Royal Society of Chemistry,

External links

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