Page last updated: 2024-11-08

calcein am

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

calcein AM: a non-fluorescent compound cleaved to a fluorescent compound by non-specific intracellular esterases [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

calcein am : An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID390986
CHEMBL ID1977168
CHEBI ID3303
SCHEMBL ID15319006
MeSH IDM0227888

Synonyms (37)

Synonym
acetoxymethyl 2-[[2-(acetoxymethoxy)-2-oxo-ethyl]-[[3',6'-diacetoxy-7'-[[bis[2-(acetoxymethoxy)-2-oxo-ethyl]amino]methyl]-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-2'-yl]methyl]amino]acetate
nsc-689290
NCI60_032172
148504-34-1
calcein am
glycine,n'-[[3',6'-bis(acetyloxy)-3-oxospiro[isobenzo furan-1(3h),9'-[9h]xanthene]-2'7'-diyl]bis(methylene)] bis[n-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, bis[(acetyloxy)methyl] ester
nsc689290
calcein-am
4',5'-bis(n,n-bis(carboxymethyl)aminomethyl)fluorescein acetoxymethyl ester
glycine, n,n'-((3',6'-bis(acetyloxy)-3-oxospiro(isobenzofuran-1(3h),9'-(9h)xanthene)-2',7'-diyl)bis(methylene))bis(n-(2-((acetyloxy)methoxy)-2-oxoethyl)-, bis((acetyloxy)methyl) ester
calcein-acetoxymethyl ester
AC1L916S ,
acetyloxymethyl 2-[[2-(acetyloxymethoxy)-2-oxoethyl]-[[3',6'-diacetyloxy-7'-[[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]methyl]-3-oxospiro[2-benzofuran-1,9'-xanthene]-2'-yl]methyl]amino]acetate
FT-0664197
acetyloxymethyl 2-[[2-(acetyloxymethoxy)-2-oxidanylidene-ethyl]-[[3',6'-diacetyloxy-7'-[[bis[2-(acetyloxymethoxy)-2-oxidanylidene-ethyl]amino]methyl]-3-oxidanylidene-spiro[2-benzofuran-1,9'-xanthene]-2'-yl]methyl]amino]ethanoate
2-[[2-(acetyloxymethoxy)-2-oxoethyl]-[[3',6'-diacetyloxy-7'-[[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]methyl]-3-oxo-2'-spiro[isobenzofuran-1,9'-xanthene]yl]methyl]amino]acetic acid acetyloxymethyl ester
A808837
AC1Q1LD2 ,
n,n'-[[3',6'-bis(acetyloxy)-3-oxospiro[isobenzofuran-1(3h),9'-[9h]xanthene]-2',7'-diyl]bis(methylene)]bis[n-[2-[(acetyloxy)methoxy]-2-oxoethyl]glycine 1,1'-bis[(acetyloxy)methyl] ester
CHEBI:3303
[({[3',6'-bis(acetyloxy)-3-oxo-3h-spiro[[2]benzofuran-1,9'-xanthene]-2',7'-diyl]bis(methylene)nitrilo}bis[(1-oxoethane-2,1-diyl)oxy]methylene)] tetraacetate
tetrakis[(acetyloxy)methyl] 2,2',2'',2'''-{[3',6'-bis(acetyloxy)-3-oxo-3h-spiro[[2]benzofuran-1,9'-xanthene]-2',7'-diyl]bis(methanediylnitrilo)}tetraacetate
SCHEMBL15319006
CHEMBL1977168
CS-7726
c46h46n2o23
HB0720
AKOS027382981
BQRGNLJZBFXNCZ-UHFFFAOYSA-N
HY-D0041
tetrakis(acetoxymethyl) 2,2',2'',2'''-(((3',6'-diacetoxy-3-oxo-3h-spiro[isobenzofuran-1,9'-xanthene]-2',7'-diyl)bis(methylene))bis(azanetriyl))tetraacetate
mfcd05861516
Q27068143
glycine, n,n'-[[3',6'-bis(acetyloxy)-3-oxospiro[isobenzofuran-1(3h),9'-[9h]xanthene]-2',7'-diyl]bis(methylene)]bis[n-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, 1,1'-bis[(acetyloxy)methyl] ester
EX-A5062
AS-78082
DTXSID101043565

Research Excerpts

Overview

Calcein AM is a prefluorochrome that is known as a substrate for multidrug efflux transporters.

ExcerptReferenceRelevance
"Calcein AM is a prefluorochrome that is known as a substrate for multidrug efflux transporters of mammalian cells."( Extrusion of fluorescein diacetate by multidrug-resistant Candida albicans.
Branchini, ML; Imai, T; Mikami, Y; Miyaji, M; Nishimura, K; Taguchi, H; Yang, HC, 2001
)
1.03

Toxicity

ExcerptReferenceRelevance
" A laboratory study was performed in a defined test model to compare the toxicity of natural and pharmaceutical tear substitutes and to identify potentially toxic factors in natural tear substitutes, such as amylase, hypotonicity, and variations in preparation."( Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells.
Cree, IA; Daniels, JT; Dart, JK; Geerling, G; Khaw, PT, 2001
)
0.31
" Preserved hypromellose was more toxic than the unpreserved preparation."( Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells.
Cree, IA; Daniels, JT; Dart, JK; Geerling, G; Khaw, PT, 2001
)
0.31
"To investigate whether the toxic effect on cultured retinal pigment epithelial (RPE) cells after application of indocyanine green is related to the osmolarity of the solvent or to toxic effects of the dye and evaluate whether these changes also occur using infracyanine green."( Toxic effect of indocyanine green on retinal pigment epithelium related to osmotic effects of the solvent.
Feron, EJ; Stalmans, I; Stalmans, P; Van Aken, EH; Veckeneer, M, 2002
)
0.31
" Trypan blue is safe in a cell culture model."( Safety testing of indocyanine green and trypan blue using retinal pigment epithelium and glial cell cultures.
Hillenkamp, J; Jackson, TL; Knight, BC; Marshall, J; Stanford, MR; Thomas, D; Zhang, JJ, 2004
)
0.32
" This study provides likely explanations for clinically observed adverse liver effects of CP-724,714."( Role of hepatic transporters in the disposition and hepatotoxicity of a HER2 tyrosine kinase inhibitor CP-724,714.
Bi, YA; Campbell, S; Davidson, R; Duignan, DB; Dunn, MC; Feng, B; Kostrubsky, VE; Mireles, R; Smith, AR; Wang, HF; Xu, JJ, 2009
)
0.35
" Adverse retinal staining was not noted and the final visual acuity showed no difference with multiple staining."( Brilliant Blue G double staining enhances successful internal limiting membrane peeling with minimal adverse effect by low cellular permeability into live cells.
Asato, R; Enaida, H; Hisatomi, T; Ikeda, Y; Ishibashi, T; Murakami, Y; Notomi, S; Oishi, S; Sakamoto, T; Tachibana, T; Yamashita, T, 2015
)
0.42
" It is one of the most toxic compounds belonging to organochlorines."( The Crucial Involvement of Retinoid X Receptors in DDE Neurotoxicity.
Kajta, M; Krzeptowski, W; Lasoń, W; Litwa, E; Rzemieniec, J; Wnuk, A; Wójtowicz, AK, 2016
)
0.43
" Additionally, adverse effects of MWCNTs at low concentration are not well understood."( Comparison of Cytotoxicity and Inhibition of Membrane ABC Transporters Induced by MWCNTs with Different Length and Functional Groups.
Cherr, GN; Li, M; Liu, S; Shen, Z; Wu, B; Yu, J; Zhang, XX, 2016
)
0.43

Pharmacokinetics

ExcerptReferenceRelevance
" Based on numerous reports implicating the role of the ATP-binding cassette drug transporter P-glycoprotein (P-gp) in ivermectin efflux in dogs, an in vivo study was conducted to determine whether ivermectin toxicity results from a pharmacokinetic interaction with spinosad."( Pharmacokinetic interaction of the antiparasitic agents ivermectin and spinosad in dogs.
Balogh, L; Dunn, ST; Hedges, L; Lai, Y; Locuson, CW; Mahabir, S; Sampson, KE, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
"Because modulation of P-glycoprotein (Pgp) through inhibition or induction can lead to drug-drug interactions by altering intestinal, central nervous system, renal, or biliary efflux, it is anticipated that information regarding the potential interaction of drug candidates with Pgp will be a future regulatory expectation."( In vitro p-glycoprotein inhibition assays for assessment of clinical drug interaction potential of new drug candidates: a recommendation for probe substrates.
Balakrishnan, A; Humphreys, JE; Keogh, JP; Kunta, JR; Polli, JW; Rautio, J; Serabjit-Singh, CJ; Webster, LO, 2006
)
0.33
" Importantly, using freshly isolated PBCECs in suspension in combination with fluorescence-activated cell sorting analysis reduced experimental time to 4hrs vs 7d with cultured PBCECs monolayers, while retaining and even improving feasibility, reliability, specificity, and sensitivity of the assay."( Rapid assessment of p-glycoprotein-drug interactions at the blood-brain barrier.
Bubik, M; Fricker, G; Mahringer, A; Ott, M, 2006
)
0.33

Bioavailability

ExcerptReferenceRelevance
" However, it cannot be excluded that co-administration of Pgp inhibitors such as ritonavir or paroxetine could increase MDMA, MDE and PMA bioavailability and also enhance brain entry leading to severe side effects."( P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.
Haefeli, WE; Ketabi-Kiyanvash, N; Mikus, G; Weiss, J, 2003
)
0.32
" Comparison of exposure to the intravenous and subcutaneous doses indicated 100% bioavailability following subcutaneous administration."( Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4.
Anastassov, V; Bodart, V; Bridger, GJ; Darkes, MC; Fricker, SP; Idzan, SR; Labrecque, J; Lau, G; Macfarland, RT; Mosi, RM; Neff, KS; Nelson, KL; Patel, K; Ruzek, MC; Santucci, Z; Scarborough, R; Wong, RS, 2009
)
0.35
" This substrate specificity of gemifloxacin towards these efflux transporters may be one of the major factors accounting for low oral bioavailability (71%)."( Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin.
Kwatra, D; Mitra, AK; Pal, D; Vadlapatla, RK; Vadlapudi, AD, 2011
)
0.37
"The membrane protein P-glycoprotein (P-gp) plays key roles in the oral bioavailability of drugs, their blood brain barrier passage as well as in multidrug resistance."( Cell-free microfluidic determination of P-glycoprotein interactions with substrates and inhibitors.
Dittrich, PS; Eyer, K; Herger, M; Krämer, SD, 2014
)
0.4
" In addition, the influence of NCB on the bioavailability of chamaechromone following their co-administration was also determined in rats."( Neochamaejasmin B increases the bioavailability of chamaechromone coexisting in Stellera chamaejasme L. via inhibition of MRP2 and BCRP.
Bi, H; Hu, H; Huang, M; Lou, Y; Pan, L; Wang, X; Zeng, K; Zeng, S, 2015
)
0.42
"P-glycoprotein (P-gp) over-expression plays a vital role in not only systemic drug bioavailability but also cancer multi-drug resistance (MDR)."( A novel flavonoid from Fissistigma cupreonitens, 5‑hydroxy‑7,8‑dimethoxyflavanone, competitively inhibited the efflux function of human P-glycoprotein and reversed cancer multi-drug resistance.
Hung, CC; Lan, YH; Lin, KI; Lin, YC; Teng, YN; Thang, TD, 2021
)
0.62

Dosage Studied

ExcerptRelevanceReference
" A dose-response curve was generated for norepinephrine in concentrations of 100 nM-100 microM."( Effect of norepinephrine on proliferation, migration, and adhesion of SV-40 transformed human corneal epithelial cells.
Araki-Sasaki, K; Campbell, S; Marfurt, CF; Murphy, CJ, 1998
)
0.3
" The inhibitory potency of the tested drugs from the dose-response relationships was cyclosporin A>verapamil> phenytoin> carbamazepine> lamotrigine>phenobarbital>valproic acid, levetiracetam, gabapentin."( Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs.
Chen, CC; Hung, CC; Lin, CJ; Liou, HH, 2008
)
0.35
"5h following subcutaneous dosing in mice and with maximum peak plasma concentration of compound preceding peak mobilization in dogs, indicating that AMD3465 has the potential to mobilize hematopoietic stem cells."( Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4.
Anastassov, V; Bodart, V; Bridger, GJ; Darkes, MC; Fricker, SP; Idzan, SR; Labrecque, J; Lau, G; Macfarland, RT; Mosi, RM; Neff, KS; Nelson, KL; Patel, K; Ruzek, MC; Santucci, Z; Scarborough, R; Wong, RS, 2009
)
0.35
" These results may provide a possible explanation for higher methadone dosage requirements in patients carrying variant-type of P-gp and revealed the possible drug-drug interactions in patients who receive concomitant drugs which are also P-gp substrates."( Functional impact of ABCB1 variants on interactions between P-glycoprotein and methadone.
Chiou, MH; Hsieh, YW; Huang, CL; Hung, CC; Lane, HY; Teng, YN, 2013
)
0.39
" A dose-response curve was generated for itraconazole and clarithromycin (maximal concentration 100 μM) and compared to that of Zosuquidar, a highly specific known P-gp inhibitor."( Itraconazole and clarithromycin inhibit P-glycoprotein activity in primary human sinonasal epithelial cells.
Bleier, BS; Han, X; Hoang, JD; Lam, A; Singleton, A, 2015
)
0.42
"Both itraconazole and clarithromycin demonstrated a dose-response curve for P-gp inhibition similar to that of Zosuquidar."( Itraconazole and clarithromycin inhibit P-glycoprotein activity in primary human sinonasal epithelial cells.
Bleier, BS; Han, X; Hoang, JD; Lam, A; Singleton, A, 2015
)
0.42
" In conclusion, these results may assist, in a mechanism-based, selection of suitable surfactants for formulating oral dosage forms to enhance the absorption of low bioavailable P-gp substrates."( Nonionic surfactants increase digoxin absorption in Caco-2 and MDCKII MDR1 cells: Impact on P-glycoprotein inhibition, barrier function, and repeated cellular exposure.
Al-Ali, AAA; Holm, R; Nielsen, CU; Steffansen, B, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fluorochromeA fluorescent dye used to stain biological specimens.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
acetate esterAny carboxylic ester where the carboxylic acid component is acetic acid.
organic heteropentacyclic compound
gamma-lactoneA lactone having a five-membered lactone ring.
oxaspiro compoundA spiro compound in which at least one of the cyclic components is an oxygen heterocyle.
2-benzofurans
xanthene dyeA dye derived by condensation of phthalic anhydride with resorcinol (and derivatives) or m-aminophenol (and derivatives).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (426)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's61 (14.32)18.2507
2000's186 (43.66)29.6817
2010's161 (37.79)24.3611
2020's18 (4.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 58.61

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index58.61 (24.57)
Research Supply Index6.08 (2.92)
Research Growth Index4.74 (4.65)
Search Engine Demand Index98.43 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (58.61)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (0.69%)6.00%
Case Studies1 (0.23%)4.05%
Observational0 (0.00%)0.25%
Other433 (99.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]