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2,3,4,5-Tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-xanthen-9-yl)benzoic acid

HCID 25474
ノート反応
基本情報概要名称と識別子物性化学と産業関連反応化合物ノート
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基本情報

CAS
152-74-9
標準SMILES
O=C(O)c1c(Cl)c(Cl)c(Cl)c(Cl)c1-c1c2cc(I)c(=O)c(I)c-2oc2c(I)c(O)c(I)cc12
InChIKey
VDNLFJGJEQUWRB-UHFFFAOYSA-N
分子式
C20H4Cl4I4O5
平均分子量
973.7 g/mol
単同位体質量
971.4992

概要

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 member of phenols, an organoiodine compound and a xanthene dye. It is functionally related to a fluorescin. It is a conjugate acid of a rose bengal(2-).

名称と識別子

優先名称
2,3,4,5-Tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-xanthen-9-yl)benzoic acid
IUPAC
2,3,4,5-tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid
英語名
Spiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-
分子式
C20H4Cl4I4O5
分子量
973.67264

名称と別名

rose-bengalrose bengal free acid2,3,4,5-Tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid152-74-9CHEBI:872022,3,4,5-tetrachloro-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-xanthen-9-yl)benzoic acidNSC10463NSC45732NSC-10463NSC270091BengalrosaRose bengale (base)
名称をさらに表示
4,5,6,7-Tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-oneSpiro(isobenzofuran-1(3H),9'(9H)-xanthen)-3-one, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-
Ak-Rose Liq 1%TetraiodotetrachlorofluoresceinGTPL2393SCHEMBL1464825CHEMBL1208422SCHEMBL29352253DTXSID20859517BDBM50541116

データベース識別子

CAS
152-74-9、4159-77-7、632-69-9
PubChem CID
25474
DTXSID

物性

構造計算による物性

XLogP
7.6
極性表面積
83.8 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
2
重原子数
33
形式電荷
0
複雑度
988

実験および物理化学的性質

Melting PointDecomposes

化学と産業

薬理情報

Protein Binding · 1 件

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.

Pharmacodynamics · 1 件

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.

Mechanism of Action · 1 件

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.

Biological Half-LifeDoses 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.
Metabolism/MetabolitesNo information available.

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性化学と産業関連反応化合物ノート
DTXSID20859517
ChEMBL
CHEMBL1208422
ChEBI
CHEBI:87202
Nikkaji
J84.910C
Absorption, Distribution and Excretion · 4 件

No information available.

Rose bengal undergoes biliary excretion.

No information available.

No information available.

Cellular LocationsMembrane

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