Chemodex

MAPTAM

Product Code:
 
CDX-B0292
Product Group:
 
Dyes, Stains, and Probes
Supplier:
 
Chemodex
Regulatory Status:
 
RUO
Shipping:
 
Ambient
Storage:
 
Short Term: +4°C. Long Term: -20°C
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Chemical Structure
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Chemical Structure

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CDX-B0292-M01010 mg£108.00
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CDX-B0292-M02525 mg£230.00
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Further Information

Alternate Names/Synonyms:
5,5'-Dimethyl-BAPTA-AM; 1,2-Bis(2-amino-5-methylphenoxy) ethane; 1,2-Bis(2-amino-5-methylphenoxy)ethane-N,N,N',N'-tetraacetic acid tetrakis(acetoxymethyl) ester
Appearance:
White to off-white powder.
CAS:
147504-94-7
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.Protect from light and moisture.
Hazards:
H315, H319, H335
InChi:
InChI=1S/C36H44N2O18/c1-23-7-9-29(37(15-33(43)53-19-49-25(3)39)16-34(44)54-20-50-26(4)40)31(13-23)47-11-12-48-32-14-24(2)8-10-30(32)38(17-35(45)55-21-51-27(5)41)18-36(46)56-22-52-28(6)42/h7-10,13-14H,11-12,15-22H2,1-6H3
InChiKey:
HEOJVQZWOLQUDR-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 147504-94-7. Formula: C36H44N2O18. MW: 792.74. Synthetic. MAPTAM is a cell permeable intracellular Ca2+ chelator that can be loaded non-invasive into cells by incubation. MAPTAM itself does not bind calcium, but once inside the cell is converted into it's derivative Dimethyl-BAPTA by cytoplasmic esterases. This type of calcium chelators are commonly used to form calcium buffers with well-defined calcium concentrations. By injecting the chelators into cells or by incubating cells with the AM ester form of the chelators, one can control the cytosolic calcium concentration, an important means to study the roles of calcium. Key advantages of these calcium chelators include relative insensitivity toward intracellular pH change and fast release of calcium. Recent studies have shown that BAPTA derivative might have microtubule disruptive activity (unrelated to it's calcium chelating activity) and should be used with caution in studies of cytoskeleton-related cell functions.
MDL:
MFCD00036856
Molecular Formula:
C36H44N2O18
Molecular Weight:
792.74
Package Type:
Vial
Precautions:
P261, P305, P351, P338
Product Description:
MAPTAM is a cell permeable intracellular Ca2+ chelator that can be loaded non-invasive into cells by incubation. MAPTAM itself does not bind calcium, but once inside the cell is converted into it's derivative Dimethyl-BAPTA by cytoplasmic esterases. This type of calcium chelators are commonly used to form calcium buffers with well-defined calcium concentrations. By injecting the chelators into cells or by incubating cells with the AM ester form of the chelators, one can control the cytosolic calcium concentration, an important means to study the roles of calcium. Key advantages of these calcium chelators include relative insensitivity toward intracellular pH change and fast release of calcium. Recent studies have shown that BAPTA derivative might have microtubule disruptive activity (unrelated to it's calcium chelating activity) and should be used with caution in studies of cytoskeleton-related cell functions.
Purity:
>94% (HPLC)
Signal word:
Warning
SMILES:
CC1=CC(OCCOC2=CC(C)=CC=C2N(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)=C(N(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)C=C1
Solubility Chemicals:
Soluble in DMSO, DMF, acetonitrile, ethyl acetate or chloroform.
Source / Host:
Synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Fluorescent Reagents
UNSPSC Number:
41105331
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

(1) Biochemistry 19, 2396 (1980) | (2) R.Y. Tsein; Nature 290, 527 (1981) | (3) J.B. Lefkowith, et al.; J. Immunol. 149, 1729 (1992) | (4) K.A. Birch, et al.; J. Cell Biol. 118, 1501 (1992) | (5) E. Poch, et al.; Biochem. J. 290, 617 (1993) | (6) J.M. Dubinsky; Neurosci. Lett. 150, 129 (1993) | (7) T. Tiffert & V.L. Lew; J. Physiol. 505, 403 (1997) | (8) J.R. Wu-Wong, et al.; Clin. Sci. 103 Suppl.48, 418S (2002) | (9) A. Furuta, et al.; Endocr. J. 56, 235 (2009) | (10) R. Chen, et al.; Microb. Pathog. 83-84, 29 (2015)