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      MAPTAM

      SKU
      B0292

      Category: Fluorescent Detection

      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
      147504-94-7
      CAS-Number
      C36H44N2O18
      Molecular Formula
      792.74
      Molecular Weight

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥94.5% (HPLC)
      Identity
      1H-NMR
      Appearance
      White to off-white powder

      Properties

      Solvents
      DMSO, DMF, acetonitrile, ethyl acetate, chloroform

      Downloads

      Safety Data Sheet
      CDX B0292 MSDS.pdf
      Handling Advice
      Protect from light and moisture.
      Use / Stability
      Stable for at least 2 years after receipt when stored at -20°C.
      Long Term Storage
      -20°C
      Short Term Storage
      +4°C
      Shipping
      AMBIENT
      Transportation
      Not dangerous goods
      Signal word
      Warning
      GHS Symbol
      GHS07
      Precautionary statements
      P261-P305 + P351 + P338
      Hazard statements
      H315-H319-H335
      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.
      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
      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)
      InChi Key
      HEOJVQZWOLQUDR-UHFFFAOYSA-N
      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

      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.

      SKU: B0292 Category: Fluorescent Detection
      • Additional information

      Additional information

      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

      Purity

      ≥94.5% (HPLC)

      Appearance

      White to off-white powder

      CAS-Number

      147504-94-7

      Molecular Formula

      C36H44N2O18

      Molecular Weight

      792.74

      Identity

      1H-NMR

      Solvents

      DMSO, DMF, acetonitrile, ethyl acetate, chloroform

      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

      InChi Key

      HEOJVQZWOLQUDR-UHFFFAOYSA-N

      Shipping

      AMBIENT

      Short Term Storage

      +4°C

      Long Term Storage

      -20°C

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      Stable for at least 2 years after receipt when stored at -20°C.

      Hazard statements

      H315-H319-H335

      Precautionary statements

      P261-P305 + P351 + P338

      GHS Symbol

      GHS07

      Signal word

      Warning

      Transportation

      Not dangerous goods

      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)

      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

      Quantity

      10 mg, 25 mg, Bulk

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