OFTASCEINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H26N2O13
Molecular Weight	622.533
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CN(CC(O)=O)CC1=CC2=C(OC3=CC(O)=C(CN(CC(O)=O)CC(O)=O)C=C3C24OC(=O)C5=C4C=CC=C5)C=C1O

InChI

InChIKey=DEGAKNSWVGKMLS-UHFFFAOYSA-N

InChI=1S/C30H26N2O13/c33-21-7-23-19(5-15(21)9-31(11-25(35)36)12-26(37)38)30(18-4-2-1-3-17(18)29(43)45-30)20-6-16(22(34)8-24(20)44-23)10-32(13-27(39)40)14-28(41)42/h1-8,33-34H,9-14H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)

HIDE SMILES / InChI

Molecular Formula	C30H26N2O13
Molecular Weight	622.533
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11167823 | https://www.google.ch/patents/US4518579 | https://www.ncbi.nlm.nih.gov/pubmed/15713203 | https://www.ncbi.nlm.nih.gov/pubmed/7970535

Oftasceine is a fluorescent dye or luminescent agent. It was recommended for the use as an effective agent for the blood-retinal barrier integrity studies. It was used to detect drug interactions with multidrug resistance proteins because it is an effective substrate of the multidrug resistance transporter 1P-glycoprotein and the multidrug resistance-related protein. The Oftasceine assay can be used as a quantitative, standardized, inexpensive screening test in a routine clinical laboratory setting. The assay detects both P-glycoprotein and multidrug resistance-associated protein activities, and identifies acute myeloid leukaemia patients with unfavorable therapy responses. It is used in ophthalmic solutions as a staining agent when fitting hydrogel contact lens. The use of a fluorexon dye-impregnated strip (pre-wetted with preservative-free saline) yielded comparable results with a fluorescein strip for assessments of tear film stability based on tear film break-up time.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Multidrug resistance 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11167823	Diagnostic		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.	2002-05-06	11986786
Application of three-dimensional quantitative structure-activity relationships of P-glycoprotein inhibitors and substrates.	2002-05	11961114
Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.	2002-05	11961113
Iron uptake and Nramp2/DMT1/DCT1 in human bronchial epithelial cells.	2002-05	11943663
Efficient intracellular drug and gene delivery using folate receptor-targeted pH-sensitive liposomes composed of cationic/anionic lipid combinations.	2002-04-23	11943407
Mitochondria are morphologically and functionally heterogeneous within cells.	2002-04-02	11927546
Resolution of P-glycoprotein and non-P-glycoprotein effects on drug permeability using intestinal tissues from mdr1a (-/-) mice.	2002-04	11959808
An improved labelling technique for monitoring microcrack growth in compact bone.	2002-04	11934422
Cholesterol modulates interaction between an amphipathic class A peptide, Ac-18A-NH2, and phosphatidylcholine bilayers.	2002-03-26	11900560
Characterization of flavonoid--biomembrane interactions.	2002-03-01	11883909
Ectopic mineralization of articular cartilage in the bullfrog Rana catesbeiana and its possible involvement in bone closure.	2002-03	11904772
Binding of ricin A-chain to negatively charged phospholipid vesicles leads to protein structural changes and destabilizes the lipid bilayer.	2002-02-26	11851431
Inhibition by R(+) or S(-) pramipexole of caspase activation and cell death induced by methylpyridinium ion or beta amyloid peptide in SH-SY5Y neuroblastoma.	2002-02-15	11835316
Coupling fiber optics to a permeation liquid membrane for heavy metal sensor development.	2002-02-01	11838692
Canine prostate induces new bone formation in mouse calvaria: A model of osteoinduction by prostate tissue.	2002-02-01	11816018
Evaluation of mitochondrial function and membrane integrity by dual fluorescent staining for assessment of sperm status in rats.	2002-02	11915365
Influence of nicotine administration on different implant surfaces: a histometric study in rabbits.	2002-02	11895287
Bromocriptine reverses P-glycoprotein-mediated multidrug resistance in tumor cells.	2002-02	11856485
Effects of immobilization followed by remobilization on mineral density, histomorphometric features, and formation of the bones of the metacarpophalangeal joint in horses.	2002-02	11843130
Tendon healing in a bone tunnel. Part II: Histologic analysis after biodegradable interference fit fixation in a model of anterior cruciate ligament reconstruction in sheep.	2002-02	11830805
In vivo RANK signaling blockade using the receptor activator of NF-kappaB:Fc effectively prevents and ameliorates wear debris-induced osteolysis via osteoclast depletion without inhibiting osteogenesis.	2002-02	11811549
Increased IRP1 and IRP2 RNA binding activity accompanies a reduction of the labile iron pool in HFE-expressing cells.	2002-02	11807826
Evaluation of the clinical relevance of the expression and function of P-glycoprotein, multidrug resistance protein and lung resistance protein in patients with primary acute myelogenous leukemia.	2002-02	11755464
Reconsideration of drug release from temperature-sensitive liposomes.	2002-01	11824566
Effect of eyelid closure and overnight contact lens wear on viability of surface epithelial cells in rabbit cornea.	2002-01	11805514
Isoflurane prevents delayed cell death in an organotypic slice culture model of cerebral ischemia.	2002-01	11753020
High throughput fluorescence assays for the measurement of mitochondrial activity in intact human neuroblastoma cells.	2001-12	11788059
Interaction of SMKT, a killer toxin produced by Pichia farinosa, with the yeast cell membranes.	2001-12	11748724
Effects of clotrimazole on transport mediated by multidrug resistance associated protein 1 (MRP1) in human erythrocytes and tumour cells.	2001-12	11737211
Rotenone inhibits the mitochondrial permeability transition-induced cell death in U937 and KB cells.	2001-11-02	11527970
Characteristics of newly formed bone during guided bone regeneration: observations by immunohistochemistry and confocal laser scanning microscopy.	2001-11	11915299
Down-regulation of cell adhesion molecules LFA-1 and ICAM-1 after in vitro treatment with the anti-TNF-alpha agent thalidomide.	2001-11	11838958
Ethanol impairs insulin-stimulated mitochondrial function in cerebellar granule neurons.	2001-11	11766890
Extrusion of fluorescein diacetate by multidrug-resistant Candida albicans.	2001-11	11766100
Intracellular drug delivery using low-frequency ultrasound: quantification of molecular uptake and cell viability.	2001-11	11758757
Amyloid beta protein forms ion channels: implications for Alzheimer's disease pathophysiology.	2001-11	11689468
Calcein-acetyoxymethyl cytotoxicity assay: standardization of a method allowing additional analyses on recovered effector cells and supernatants.	2001-11	11687452
Effects of the acyl chain composition of phosphatidylcholines on the stability of freeze-dried small liposomes in the presence of maltose.	2001-11	11687225
Intracellular delivery mediated by an ethosomal carrier.	2001-11	11575480
Visualizing normal and defective bone development in zebrafish embryos using the fluorescent chromophore calcein.	2001-10-15	11784007
Investigation of the cellular uptake of E-Selectin-targeted immunoliposomes by activated human endothelial cells.	2001-10-01	11557019
Localization of zinc after in vitro mineralization in osteoblastic cells.	2001-10	11694001
Autologous serum eyedrops for dry eyes and epithelial defects: clinical and in vitro toxicity studies.	2001-10	11567963
Mechanism of clofibrate hepatotoxicity: mitochondrial damage and oxidative stress in hepatocytes.	2001-09-01	11522451
The extent of matrix damage and chondrocyte death in mechanically traumatized articular cartilage explants depends on rate of loading.	2001-09	11562121
Cell mediated cytotoxicity assessment by relative changes in viable target absolute counts.	2001-08	11694035
Glycine blocks opening of a death channel in cultured hepatic sinusoidal endothelial cells during chemical hypoxia.	2001-08	11526438
Sonoluminescence as an indicator of cell membrane disruption by acoustic cavitation.	2001-06	11516544
Masticatory muscle function and transverse dentofacial growth.	2001	11803645
The effect of micromovement on callus formation.	2001	11793181

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:33 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:33 GMT 2025`
Record UNII	V0YM2B16TS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-298193

Preferred Name

English

OFTASCEINE

Official Name

English

GLYCINE, N,N'-((3',6'-DIHYDROXY-3-OXOSPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHENE)-2',7'-DIYL)BIS(METHYLENE))BIS(N-(CARBOXYMETHYL)-

Systematic Name

English

CALCEIN

Common Name

English

oftasceine [INN]

Common Name

English

FLUORESCEIN COMPLEXON

Common Name

English

FLUOREXON

Common Name

English

2',7'-BIS((BIS(CARBOXYMETHYL)AMINO)METHYL)FLUORESCEIN

Common Name

English

Oftasceine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C461