Photo-BAPTA, Tetramethyl Ester
Photo-BAPTA, tetramethyl ester
Highlights:
- A precursor to the only photo-labile analog of BAPTA available on the market
- Photo-BAPTA (produced upon saponification) has a very high affinity towards Ca2+ ions (K = 2, 500, 000 1/M)
- Very efficient calcium ion release (quantum yield of 63%) upon UVA or UVB irradiation
- Releases Ca2+ ions within 12 microseconds upon excitation
- Quantitative calcium release
- Suitable for time- and spatially- resolved generation of calcium ion concentration spikes
- Long shelf life in the dark
A precursor to very efficient and novel photocleavable analog of BAPTA, a calcium ion selective high-affinity chelator ligand. Free calcium ions (Ca2+) play an important role as a secondary messenger for a wide variety of regulatory functions in physiological and biological processes in cells. The fluctuations of intracellular Ca2+ concentration regulate many cellular functions, such as neurotransmitter release, operation of ion channels in the plasma membrane, hormone secretion, muscle contraction, and many others. In recent years, the flash photolysis of photoresponsive calcium-ion chelators has become a common method in biochemical studies. The light-triggered release of free Ca2+ allows for following the system response to a spike in calcium ion concentration.
From the laboratory of Vladimir V. Popik, PhD, University of Georgia.
Photo-BAPTA, tetramethyl ester
Highlights:
- A precursor to the only photo-labile analog of BAPTA available on the market
- Photo-BAPTA (produced upon saponification) has a very high affinity towards Ca2+ ions (K = 2, 500, 000 1/M)
- Very efficient calcium ion release (quantum yield of 63%) upon UVA or UVB irradiation
- Releases Ca2+ ions within 12 microseconds upon excitation
- Quantitative calcium release
- Suitable for time- and spatially- resolved generation of calcium ion concentration spikes
- Long shelf life in the dark
A precursor to very efficient and novel photocleavable analog of BAPTA, a calcium ion selective high-affinity chelator ligand. Free calcium ions (Ca2+) play an important role as a secondary messenger for a wide variety of regulatory functions in physiological and biological processes in cells. The fluctuations of intracellular Ca2+ concentration regulate many cellular functions, such as neurotransmitter release, operation of ion channels in the plasma membrane, hormone secretion, muscle contraction, and many others. In recent years, the flash photolysis of photoresponsive calcium-ion chelators has become a common method in biochemical studies. The light-triggered release of free Ca2+ allows for following the system response to a spike in calcium ion concentration.
From the laboratory of Vladimir V. Popik, PhD, University of Georgia.
| Product Type: | Small Molecule |
| Name: | Photo-BAPTA, tetramethyl ester |
| Alternative Name(s): | tetramethyl 2,2',2'',2'''-((((1-(3-hydroxynaphthalen-2-yl)ethane-1,2-diyl)bis(oxy))bis(2,1-phenylene))bis(azanetriyl))tetraacetate |
| Chemical Formula: | C36H38N2O11 |
| CAS number: | 2102527-61-5 |
| Molecular Weight: | 674.69 |
| Format: | yellowish crystals |
| Purity: | >98% 1HNMR |
| Solubility: | MeOH, EtOH, EtOAc, CH3CN, THF, CH2Cl2 |
| Spectral Information: |
IR: 3381 (broad); 2951; 1732; 1501; 1194; 1168; 743 cm-1 1H-NMR: 7.79 (1H, s); 7.73 (1H, d, J = 8.4 Hz); 7.62 (1H, d, J = 8.4 Hz); 7.52 (1H, s); 7.40-7.36 (1H, m); 7.31-7.27 (1H,m); 7.20 (1H, s); 6.92-6.87 (5H, m); 6.82-6.75 (3H, m); 6.05 (1H,dd, J = 8.8 and 3.2 Hz); 4.65 (1H, m); 4.21 (1H, dd, J = 10.0 and 3.2 Hz); 4.16 (4H, s); 4.14 (4H, s); 3.56 (6H, s); 3.49 (6H, s) 13C-NMR: 172.4; 171.8; 152.7; 150.4; 148.8; 140.0; 139.0; 134.6; 128.7; 128.3; 127.6; 126.6; 126.1; 124.5;123.6; 122.8; 122.7; 121.7; 121.4; 120.1; 119.6; 114.7; 112.9; 112.3; 77.5; 70.6; 53.6; 53.0; 51.7; 51.5 ESI HRMS: m/z: calcd. for C36 H38 N2 O11 [M+H]+ 675.2554, found 675.2555 |
| Storage: | +10C |
| Shipped: | Ambient Temperature |
- Mariia V. Sutton , Matthew McKinley , Revathy Kulasekharan and Vladimir V. Popik: Photo-cleavable analog of BAPTA for the fast and efficient release of Ca2+. (2017) Chem. Commun., 53, 5598-5601
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