Rose Bengal
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Rose Bengal
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CAS No:
11121-48-5
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Chemical Name:
Rose Bengal
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Synonyms:
Rose Bengal;Bengal Rose;Rose Bengale;HFinCl4I4;RB 1017
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CAS No:
Description
Rose bengal free acid is a xanthene dye that is fluorescein bearing bromine substituents at positions 2', 4', 5' and 7' (on the xanthene ring) and iodine substituents at position 2, 3, 4, and 5 (on the phenyl ring). The dipotassium salt is the biological stain 'rose bengal'. It has a role as a fluorochrome. It is a member of benzoic acids, a tetrachlorobenzene, a xanthene dye, a member of phenols and an organoiodine compound. It derives from a fluorescin. It is a conjugate acid of a rose bengal(2-).|Rose bengal is a pink stain derived as an analogue of fluorescein. Its disodium salt in ophthalmic solutions has been used as a diagnostic agent in suspected damage to conjunctival and corneal cells. It is also used in laboratory settings, including the preparation of Foraminifera for microscopic analysis and suppression of bacterial growth in several microbiological media. A direct cytotoxic effect of Rose bengal on microorganisms and cancer cells has been observed, questioning its potential antitumor actions via intralesional injections. The clinical applications of rose bengal as injectable formulation under the name PV-10 in melanoma, breast cancer and skin conditions such as eczema and psoriasis are being investigated in clinical trials.
Toxicity
Rose Bengal induces cytotoxic effects in different cell lines.
Tear component comprising of different proteins, such as albumin (although not very common as tear component), lactoferrin, and transferrin, can bind to rose bengal dye and act as diffusion barrier to prevent dye uptake by cells and subsequent cell staining. Lysosymes in tear film can also bind to rose bengal to form precipitates to attenuate cell uptake.
Drug Information
Indicated as a diagnostic agent in routine ocular examinations or when superficial conjunctiva or corneal tissue change is suspected, and as an aid in the diagnosis of keratoconjunctivitis sicca, keratitis, abrasions or corrosions as well as the detection of foreign bodies.
Rose bengal is a staining agent that visualized ocular surfaces of both diseased and dead cells _in vivo_. It has also shown to stain healthy cultured cells, including rabbit corneal epithelial cells, in a rapid, dose-dependent manner. Various studies demonstrate the cytotoxic effects of rose bengal in different cell cultures, including smooth-muscle cells from human intestine, endothelial cells from bovinepulmonary artery, rabbit Tenon fibro-blasts, and rabbit and human corneal epithelial cells. Cellular morphological changes such as detachment, separation, loss of motility and disruption, in addition to swelling, intracytoplasmic vacuole formation and lysis have been manifested with the treatment of rose bengal, indicating that rose Bengal is not a vital dye.
No information available.|Rose bengal undergoes biliary excretion.
No information available.
Doses between 0.01 and 10 mg/kg in rat resulted in an initial biological half-life of 2 min and a terminal half-life of 100 min. The biological half-life for excretion is around 30 minutes in rats and rabbits.
Rose Bengal stains both the nuclei and cell walls of dead or degenerated epithelial cells of the cornea and conjunctiva, and stain the mucus of the precorneal tear film. It is proposed that the staining ability of rose bengal is dependent on the status of tear film protection rather than cell viability, as tear components such as albumin and mucin can block the rose bengal uptake. It induces intrinsic cytotoxic effects by causing cellular morphologic changes, subsequent loss of cellular motility, cell detachment, and cell death. It mediates inhibitory actions on bovine corneal endothelial cells and attenuates cell proliferation.
Computed Properties
Molecular Weight:973.7
XLogP3:7.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:973.4962
Monoisotopic Mass:971.4992
Topological Polar Surface Area:83.8
Heavy Atom Count:33
Complexity:988
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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