Rose bengal
| Rose bengal | |
|---|---|
 |
|
|
4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H- spiro[isobenzofuran-1,9'-xanthen]-3-one |
|
|
Other names
C.I. 45440 |
|
| Identifiers | |
| CAS number | 11121-48-5  |
| ChEMBL | CHEMBL1160160  |
| Jmol-3D images | Image 1 |
|
|
| Properties | |
| Molecular formula | C20H4Cl4I4O5 |
| Molar mass | 973.67 g mol−1 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
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 trials as well.
Contents |
[edit] Chemical applications
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 [2 + 2] cycloadditions with alkenes and similar systems.
[edit] Biological applications
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.[1]
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.[2][3]
Rose bengal has been used for 50 years to diagnose liver and eye cancer. It has also been used as an insecticide.[4][5]
Rose Bengal is being researched as an agent in creating nano sutures.[6] 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.[7][8][9] Healing is faster and the seal reduces chances of infection.[10][11]
Rose Bengal is used in several microbiological media, including Cooke's Rose Bengal agar, to suppress bacterial growth.
[edit] Electronic applications
Rose Bengal demonstrates at least six distinct electronic properties[12] 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.
[edit] References
- ^ Metastatic Melanoma PV-10 Trial Results Encouraging Says Drug Company, Medical News Today, 09 Jun 2009
- ^ Salber D, et al. (2006). "Differential uptake of [18F]FET and [3H]l-methionine in focal cortical ischemia". Nuclear Medicine and Biology 33 (8): 1029–1035. doi:10.1016/j.nucmedbio.2006.09.004. PMID 17127177.
- ^ Watson BD, Dietrich WD, Busto R, Wachtel MS, Ginsberg MD (1985). "Induction of reproducible brain infarction by photochemically initiated thrombosis". Ann Neurol 17 (5): 497–504. doi:10.1002/ana.410170513. PMID 4004172.
- ^ Capinera, John L.; Squitier, Jason M. (2000). "Insecticidal Activity of Photoactive Dyes to American and Migratory Grasshoppers (Orthoptera: Acrididae)". Journal of Economic Entomology 93 (3): 662–666. doi:10.1603/0022-0493-93.3.662. PMID 10902313.
- ^ Martin, Phyllis; Mischke, Sue; Schroder, Robert (1998). "Compatibility of Photoactive Dyes with Insect Biocontrol Agents". Biocontrol Science and Technology 8 (4): 501–508. doi:10.1080/09583159830018.
- ^ Chan, B; Chan, O; So, K (2008). "Effects of photochemical crosslinking on the microstructure of collagen and a feasibility study on controlled protein release". Acta Biomaterialia 4 (6): 1627–1636. doi:10.1016/j.actbio.2008.06.007. PMID 18640085.
- ^ 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. (2007). "Microvascular anastomosis using a photochemical tissue bonding technique". Lasers in Surgery and Medicine 39 (9): 716–722. doi:10.1002/lsm.20548. PMID 17960755.
- ^ Mulroy L., Kim J., Wu I., Scharper P., Melki S.A., Azar D.A., Redmond R.W., Kochevar I.E. (2000). "Photochemical keratodesmos for repair of lamellar corneal incisions". Invest Ophthalmol Vis Sci 41 (11): 3335–3340. PMID 11006222.
- ^ Proano C.E., Mulroy L., Erika Jones E., Azar D.A., Redmond R.W., Kochevar I.E. (2004). Invest Ophthalmol Vis Sci: 2177–2181.
- ^ Laser Show in the Surgical Suite, Technology Review, March/April 2009
- ^ Laser Show in the Surgical Suite, Technology Review, 02.11.2009
- ^ 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,
