BAPTA tetramethyl ester | CAS 125367-34-2

Catalog Number	A14-0066
Category	Calcium, Chloride and Other indicators
Molecular Formula	C26H32N20O10
Molecular Weight	532.54

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Product Introduction

BAPTA tetramethyl ester is a lipophilic diester form of BAPTA used for inhibition of proteolytic activities of certain metalloproteinases.

Chemical Information
Application

Synonyms	Tetramethyl 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetate; Tetramethyl 2,2',2'',2'''-(((ethane-1,2-diylbis(oxy))-bis(2,1-phenylene))bis(azanetriyl))tetraacetate
Canonical SMILES	COC(=O)CN(CC(=O)OC)C1=CC=CC=C1OCCOC2=CC=CC=C2N(CC(=O)OC)CC(=O)OC
InChI	InChI=1S/C26H32N2O10/c1-33-23(29)15-27(16-24(30)34-2)19-9-5-7-11-21(19)37-13-14-38-22-12-8-6-10-20(22)28(17-25(31)35-3)18-26(32)36-4/h5-12H,13-18H2,1-4H3
InChIKey	LCPLRKMZANZSAJ-UHFFFAOYSA-N
Appearance	White Solid

BAPTA tetramethyl ester is a specialized chemical compound known as a lipophilic diester of BAPTA (1,2-bis(o-aminophenoxy)ethane-N,N,N’,N’-tetraacetic acid). This compound is structurally engineered to permeate cellular membranes, an ability facilitated by its esterified form, which renders it more hydrophobic compared to its parent compound, BAPTA. Upon entering the cell, intracellular esterases cleave the ester bonds, releasing the active BAPTA anion. This process enhances the efficacy of BAPTA within cells, enabling it to function effectively as a calcium chelator.

One of the primary applications of BAPTA tetramethyl ester is in the study of calcium signaling within cells. Its ability to efficiently pass through cellular membranes and subsequently bind to calcium ions renders it an invaluable tool in physiological and biochemical research. By chelating calcium ions, BAPTA tetramethyl ester helps in buffering intracellular calcium concentrations, thereby permitting detailed studies of calcium-dependent processes and pathways, including muscle contraction and neurotransmitter release.

BAPTA tetramethyl ester is also used in the inhibition of certain metalloproteinases. By regulating intracellular calcium levels, it indirectly influences the activity of calcium-dependent enzymes, including various metalloproteinases. These enzymes are crucial in tissue remodeling and can be implicated in disease processes. Thus, BAPTA tetramethyl ester is often used in experimental setups aimed at understanding or inhibiting the proteolytic activities of these enzymes.

Furthermore, BAPTA tetramethyl ester plays a role in neuroprotection research. Its ability to modulate intracellular calcium levels makes it a candidate for studies focused on preventing calcium-mediated neuronal damage, which is a common pathway in neurodegenerative diseases. By diminishing calcium overload, this compound helps in preserving neuronal integrity against pathological stimuli.

Lastly, BAPTA tetramethyl ester is utilized in cardiac research, particularly in the investigation of arrhythmia and other heart conditions linked to calcium dysregulation. In experimental cardiology, this compound serves as a vital tool in dissecting the role of calcium signaling in cardiac myocytes, thereby advancing our understanding of the electrophysiological and contractile properties of the heart.