BTC AM

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BTC AM

BTC AM | 176767-94-5

Catalog Number A14-0017
Category Calcium, Chloride Indictors and Other indicators
Molecular Formula C45H45N3O20S
Molecular Weight 979.9
Catalog Number Size Price Quantity
A14-0017 -- $--

Product Introduction

BTC AM is a cell-permeable acetoxy-methyl ester of BTC, a low affinity calcium indicator. BTC AM is hydrolyzed by intracellular esterases to produce BTC. It exhibits a shift in the excitation maximum from approximately 480 to 401 nm upon calcium binding, enabling determination of ratiometric calcium measurements.

Chemical Information

Synonyms N-[2-[(acetyloxy)methoxy]-2-oxoethyl]-N-[3-(2-benzothiazolyl)-6-[2-[2-[bis[2-[(acetyloxy)methoxy]-2-oxoethyl]amino]-5-methylphenoxy]ethoxy]-2-oxo-2H-1-benzopyran-7-yl]-glycine(acetyloxy)methyl ester
Purity ≥90%
IUPAC Name acetyloxymethyl 2-[N-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[3-(1,3-benzothiazol-2-yl)-7-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-2-oxochromen-6-yl]oxyethoxy]-4-methylanilino]acetate
Canonical SMILES CC1=CC(=C(C=C1)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)OCCOC2=C(C=C3C(=C2)C=C(C(=O)O3)C4=NC5=CC=CC=C5S4)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
InChI InChI=1S/C45H45N3O20S/c1-26-10-11-34(47(18-40(53)64-22-60-27(2)49)19-41(54)65-23-61-28(3)50)37(14-26)58-12-13-59-38-16-31-15-32(44-46-33-8-6-7-9-39(33)69-44)45(57)68-36(31)17-35(38)48(20-42(55)66-24-62-29(4)51)21-43(56)67-25-63-30(5)52/h6-11,14-17H,12-13,18-25H2,1-5H3
InChI Key JHWYIECNPLLVMW-UHFFFAOYSA-N
Appearance Solid Powder
  • Product Specification
  • Application
Excitation 401 nm (Ca2+-bound), 480 nm
Emission 529 nm
Storage Store at -20°C

BTC AM, known as 1,2-bis(o-aminophenoxy)ethane-N,N,N’,N’-tetraacetic acid-acetoxymethyl ester, is a synthetic biochemical compound that serves as a precursor to BTC, a well-regarded calcium indicator within cellular studies. BTC AM is cell-permeable, making it practical for use in live cell imaging. Once inside the cell, BTC AM is hydrolyzed by intracellular esterases, releasing BTC, which remains inside the cell to monitor calcium levels. Upon binding with calcium ions, BTC undergoes a conformational change that results in a notable shift in fluorescence excitation from approximately 480 nm to 401 nm. This property allows for ratiometric measurement, an advantage that enhances quantitative calcium ion studies by reducing discrepancies caused by variable dye loading and cell thickness.

One of the key applications of BTC AM is its use in cellular physiology research to monitor calcium signaling pathways. Calcium ions are critical secondary messengers in various cellular processes including muscle contraction, neurotransmitter release, and gene expression. Utilizing BTC AM, researchers can observe intracellular calcium fluctuations in real-time, providing insights into the dynamics of calcium-dependent pathways and potentially identifying dysfunctions in diseases such as cardiovascular disorders, where calcium signaling is pivotal.

Another significant application is in pharmacological testing, where BTC AM is employed to evaluate the effects of new drugs on cellular calcium dynamics. By observing changes in calcium signaling upon drug treatment, researchers can infer information about a drug’s mode of action, its efficiency, and potential side effects. This application is particularly useful during the early stages of drug development, enabling the identification of candidate molecules for further investigation in therapeutic contexts.

BTC AM is also valuable in neuroscience research. Calcium ions play a crucial role in synaptic activity and neuronal signaling. By labeling neurons with BTC AM, scientists can study the temporal and spatial patterns of neuronal firing and synaptic plasticity, contributing to a better understanding of learning and memory processes. Additionally, it aids in elucidating the pathophysiology of neurological disorders where calcium signaling is disrupted, such as in Alzheimer’s disease.

Lastly, BTC AM is used extensively in research involving the study of calcium-dependent cell signaling in immunology. The compound assists in investigating how calcium ion fluctuations affect immune cell activation, proliferation, and differentiation. By providing clear and quantitative measurements of calcium dynamics, BTC AM enables researchers to dissect complex immune signaling networks, potentially contributing to the development of more targeted immune therapies and vaccines.

Computed Properties

XLogP3 5.9
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 24
Rotatable Bond Count 32
Exact Mass 979.23171201 g/mol
Monoisotopic Mass 979.23171201 g/mol
Topological Polar Surface Area 303Ų
Heavy Atom Count 69
Formal Charge 0
Complexity 1800
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
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