
5-Bromo-5'-methyl BAPTA tetramethyl ester
| Catalog Number | A14-0119 |
| Category | Calcium, Chloride and Other indicators |
| Molecular Formula | C27H33BrN2O10 |
| Molecular Weight | 625.46 |
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Product Introduction
5-Bromo-5'-methyl BAPTA tetramethyl ester is a specialized calcium chelator bearing a brominated aromatic structure, which is integral to its role in fluorescence-based calcium detection assays. It features a tetramethyl ester moiety that facilitates cell permeability, making it suitable for intracellular calcium imaging applications. This compound is often incorporated into fluorescence microscopy workflows to monitor calcium fluxes in live cells, supporting research in cellular signaling and physiology.
Chemical Information
Application
Computed Properties
Chemical Information
| IUPAC Name | methyl 2-[2-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-bromophenoxy]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=CC(=C2)Br)N(CC(=O)OC)CC(=O)OC |
| InChI | InChI=1S/C27H33BrN2O10/c1-18-6-8-20(29(14-24(31)35-2)15-25(32)36-3)22(12-18)39-10-11-40-23-13-19(28)7-9-21(23)30(16-26(33)37-4)17-27(34)38-5/h6-9,12-13H,10-11,14-17H2,1-5H3 |
| InChIKey | SXCYTVPSAWGQKM-UHFFFAOYSA-N |
| Appearance | Solid Powder |
Application
5-Bromo-5'-methyl BAPTA tetramethyl ester is a cell-permeable BAPTA-based calcium chelator designed for fluorescence-based calcium imaging workflows. The brominated BAPTA scaffold provides a reactive handle for subsequent derivatization while the tetramethyl ester masking groups support intracellular loading prior to ester hydrolysis and calcium binding. In practice, researchers use this reagent to build calcium-sensitive staining and probe-conjugate formats that report Ca2+ dynamics with fluorescence readouts.
1. Calcium Imaging Probe Building
5-Bromo-5'-methyl BAPTA tetramethyl ester is used as a chelator platform in fluorescence probe development for monitoring intracellular Ca2+ transients. Chemical biology groups incorporate the BAPTA core into labeling strategies that couple calcium binding to an optical reporter, enabling construction of Ca2+-responsive conjugates for microscopy studies of signaling kinetics. The brominated functionality supports downstream attachment to dyes, polymers, or biomolecule carriers during probe assembly, supporting modular design of calcium imaging reagents.
2. Intracellular Ca2+ Loading
5-Bromo-5'-methyl BAPTA tetramethyl ester is commonly applied as a calcium-binding loading reagent to modulate and buffer intracellular Ca2+ during imaging experiments. Cell biology labs use BAPTA ester forms to achieve intracellular chelation after uptake, allowing controlled suppression or shaping of Ca2+ signals elicited by stimulation protocols. This use is especially relevant when researchers need a chemical tool to control Ca2+-dependent fluorescence responses in live-cell microscopy experiments.
3. Fluorescence Assay Reagent Development
5-Bromo-5'-methyl BAPTA tetramethyl ester supports the development of fluorescence-based Ca2+ assays and assay controls in solution-phase or plate-based formats. Biochemical assay teams employ BAPTA chelators to tune free Ca2+ levels and to validate calcium-dependent signal behavior in fluorescence readouts. The brominated scaffold also enables reagent customization for building Ca2+-modulating components within experimental assay panels, including conjugate-based standards used during method development.
4. Bioconjugated Calcium Tools
5-Bromo-5'-methyl BAPTA tetramethyl ester is used in biomaterials and chemical biology to generate bioconjugated calcium-handling tools for targeted or localized Ca2+ modulation. Researchers functionalize surfaces, polymer matrices, or carrier constructs with BAPTA motifs to create Ca2+-responsive microenvironments that can influence calcium-sensitive readouts. This approach is used in materials science and microscopy-oriented studies where spatial control of Ca2+ buffering is required alongside fluorescence measurements.
Computed Properties
| XLogP3 | 4.5 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 19 |
| Exact Mass | 624.13186 g/mol |
| Monoisotopic Mass | 624.13186 g/mol |
| Topological Polar Surface Area | 130Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 795 |
| 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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