5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester | CAS 124903-67-9

Catalog Number	A14-0065
Category	Calcium, Chloride and Other indicators
Molecular Formula	C28H34N2O12
Molecular Weight	590.58

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Product Introduction

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester is a calcium-sensitive fluorescent dye that belongs to the class of BAPTA-based chelators, known for their ability to bind divalent cations. This compound features a conjugated aromatic system that facilitates its chromophore functionality, allowing for specific excitation and emission properties useful in calcium imaging studies. As a tetramethyl ester derivative, it can undergo hydrolysis in biological environments, enabling its incorporation into live cell imaging workflows where it functions as a reporter molecule for intracellular calcium dynamics.

Chemical Information
Application

Chemical Information

Synonyms	methyl 2-[2-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-formyl-4-hydroxyphenoxy]ethoxy]-N-(2-methoxy-2-oxoethyl)-4-methylanilino]acetate
SMILES	CC1=CC(=C(C=C1)N(CC(=O)OC)CC(=O)OC)OCCOC2=C(C=C(C(=C2)C=O)O)N(CC(=O)OC)CC(=O)OC
InChI	InChI=1S/C28H34N2O12/c1-18-6-7-20(29(13-25(33)37-2)14-26(34)38-3)23(10-18)41-8-9-42-24-11-19(17-31)22(32)12-21(24)30(15-27(35)39-4)16-28(36)40-5/h6-7,10-12,17,32H,8-9,13-16H2,1-5H3
InChIKey	PNYGKPHFMMVHMT-UHFFFAOYSA-N
Appearance	Solid Powder

Application

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester is a BAPTA-derived, ester-protected fluorescent chelator that integrates a formyl handle for conjugation with an additional hydroxy functionality for calcium-binding behavior. In fluorescence-based calcium studies, this type of scaffold is used to build molecular imaging reagents and labeling tools where controlled Ca2+ coordination is translated into a measurable optical response, while the formyl group enables attachment to biomolecules or surfaces for targeted experimental workflows.

1. Calcium Imaging Reagent Design

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester is used by chemical biology and fluorescence probe developers to construct Ca2+-responsive imaging reagents for microscopy workflows. Researchers incorporate the formyl functionality to prepare conjugates that can be tethered to peptides, proteins, or targeting ligands, enabling localized calcium reporting in defined experimental contexts. The BAPTA framework supports the common "chelator-to-fluorescence" strategy used for optical readouts of intracellular or compartmental calcium dynamics in instrument-based imaging studies.

2. Biomolecule Conjugation For Labeling

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester supports bioconjugation-driven labeling strategies where calcium sensing needs to be associated with a specific biomolecule. In practice, laboratories use the formyl group as a functional handle to link the chelator scaffold into larger probe constructs, such as conjugates for tracking calcium near a protein of interest or along a biomolecular assembly. This approach is frequently adopted in assay development and molecular imaging reagent optimization, where probe placement and local environment strongly influence the usefulness of the optical signal.

3. Fluorescent Probe Construction Platforms

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester is commonly incorporated into fluorescent probe construction workflows for developing Ca2+-dependent fluorescence assays. Research groups use the chelator scaffold as a building block to assemble Ca2+-responsive reporter systems compatible with standard fluorescence measurement setups, including plate-based readouts and microscopy imaging. The tetramethyl ester protection pattern is leveraged in probe design to manage how the chelator scaffold is presented within the experimental system, supporting downstream evaluation of signal behavior under calcium-variable conditions.

4. Surface Immobilized Calcium Sensors

5-Formyl-4-hydroxy-5'-methyl-BAPTA tetramethyl ester is also used in materials and biomaterials research to create surface-associated calcium sensing layers. By using the formyl functionality to enable immobilization chemistry, researchers can integrate the chelator motif into coatings, functionalized polymers, or sensor surfaces where calcium-dependent optical responses are monitored. This application is particularly relevant for engineering platforms that require spatially defined sensing regions rather than freely diffusing probes, such as microenvironment studies on engineered substrates.