ROSE BENGAL LACTONE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H4Cl4I4O5
Molecular Weight	973.673
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(I)C=C2C(OC3=C(C=C(I)C(O)=C3I)C24OC(=O)C5=C4C(Cl)=C(Cl)C(Cl)=C5Cl)=C1I

InChI

InChIKey=IICCLYANAQEHCI-UHFFFAOYSA-N

InChI=1S/C20H4Cl4I4O5/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28/h1-2,29-30H

HIDE SMILES / InChI

Molecular Formula	C20H4Cl4I4O5
Molecular Weight	973.673
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.jstage.jst.go.jp/article/jjfcs/18/3/18_KJ00007729478/_article
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11931626 | https://www.ncbi.nlm.nih.gov/pubmed/11695899 | https://www.ncbi.nlm.nih.gov/pubmed/10704233 | http://pubs.acs.org/doi/abs/10.1021/ja00332a021 | https://www.ncbi.nlm.nih.gov/pubmed/24405273

Rose Bengal lactone is a polyhalogenated derivative of Fluorescein. Rose Bengal lactone is a dye compound described to produce cell membrane damage. Rose Bengal lactone and other Fluorescein derivatives are also described to modulate the function of ATP-sensitive K+ channels. Rose bengal lactone reacts readily with bases so treatment with triethylamine immediately yields the Rose Bengal salt.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-galactosidase 4 Target ID: CHEMBL2522 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11931626	Inhibitor 8297	80.0 µM [IC50]
Insulin receptor 13 Target ID: CHEMBL1981 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11695899	Agonist 2678	20.0 µM [Kd]
Beta-lactamase AmpC 3 Target ID: CHEMBL2026 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11931626	Inhibitor 8297	16.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The promoting effects of food dyes, erythrosine (Red 3) and rose bengal B (Red 105), on thyroid tumors in partially thyroidectomized N-bis(2-hydroxypropyl)-nitrosamine-treated rats.	1988 Mar	2836348

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Rose Bengal lactone at 20 times the IC50 or DMSO alone was incubated with 10 nM beta-lactamase in 10 kDa dialysis tubing. Ten milliliters of this solution was dialyzed at room temperature against three 1 L volumes of 50 mM KPi buffer, pH 7.0, exchanged hourly. After dialysis, the incubation solution was diluted 10-fold and assayed for beta-lactamase activity against 100 mkM cephalothin.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:53 UTC 2023` Edited by `admin` on `Fri Dec 15 15:08:53 UTC 2023`
Record UNII	BIU7Q7W2SH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROSE BENGAL LACTONE

Common Name

English

SPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHEN)-3-ONE, 4,5,6,7-TETRACHLORO-3',6'-DIHYDROXY-2',4',5',7'-TETRAIODO-

Systematic Name

English

FLUORESCEIN, 4,5,6,7-TETRACHLORO-2',4',5',7'-TETRAIODO-

Common Name

English

NSC-45732

Code

English

BENZOIC ACID, 2,3,4,5-TETRACHLORO-6-(6-HYDROXY-2,4,5,7-TETRAIODO-3-OXO-3H-XANTHEN-9-YL)-

Systematic Name

English

SOLVENT RED 141

Common Name

English

BLUE 7

Common Name

English

C.I.45440:1

Common Name

English

BENGAL ROSE B

Common Name

English

ROSE BENGAL ACID

Common Name

English

C.I. SOLVENT RED 141

Common Name

English

4,5,6,7-TETRACHLORO-2',4',5',7'-TETRAIODOFLUORESCEIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C461