Synthesis of APTRA Derivatives as Building Blocks for Low-Affinity Fluorescent Ca²⁺ Indicators

Abstract

A new method for the synthesis of trialkyl aminophenoltriacetates (APTRA triesters) and the functionalization of these into suitable building blocks for potential fully conjugated low-affinity fluorescent Ca²⁺ indicators are described.

Key words

heterocycles - supramolecular chemistry - aminophenoltriacetate - intracellular calcium - fluorescence - indicator

References

• 1a Otten PA. London RE. Levy LA. Bioconjugate Chem.  2001,  12:  76 
• 1b Otten PA. London RE. Levy LA. Bioconjugate Chem.  2001,  12:  203 
• 2 Tsien RY. Biochemistry  1980,  19:  2396 
• 3a Tsien RY. Annu. Rev. Neurosci.  1989,  12:  227 
• 3b Scheenen WJJM. Hofer AM. Pozzan T. In Cell Biology: A Laboratory Handbook   Vol. 3, 2nd ed.:  Celis JE. Academic Press; New York: 1998.  p.363 
• 3c Takahashi A. Camacho P. Lechleiter JD. Herman B. Physiol. Rev.  1999,  79:  1089 
• 4a Berridge MJ. Bootman MD. Lipp P. Nature (London)  1998,  395:  645 
• 4b Berridge MJ. Lipp P. Bootman MD. Nature Rev. Mol. Cell Biol.  2000,  1:  11 
• 4c Berridge MJ. Cell Calcium  2002,  32:  235 
• 5 Haugland RP. In Handbook of Fluorescent Probes and Research Products   9th ed.:  Molecular Probes; Eugene, OR, USA: 2002. 
• 6 Freedman HH. Frost AE. J. Org. Chem.  1958,  23:  1292 
• 7a Cielen E. Stobiecka A. Tahri A. Hoornaert GJ. De Schryver FC. Gallay J. Vincent M. Boens N. J. Chem. Soc. Perkin Trans. 2  2002,  6:  1197 
• 7b Cielen E. PhD Dissertation   University of Leuven; Belgium: 1999. 
• 8 Appukkuttan P. Van der Eycken E. Dehaen W. Synlett  2003,  1204 
• 9 Abramov MA. Ceulemans E. Jackers C. Van der Auweraer M. Dehaen W. Tetrahedron  2001,  9123 
• 10 Hiskey RG. Carroll FI. Babb RM. Bledsoe JO. Pucket RT. Roberts BW. J. Org. Chem.  1961,  26:  1152 
• 11 Hunter RF. Jones JWT. J. Chem. Soc., Abstr.  1930,  941 
• 12 Meth-Cohn O. Narine B. Tarnowski B. Hayes R. Keyzad A. Rhouati S. Robinson A. J. Chem. Soc., Perkin Trans. 1  1981,  9:  2509 
• 13 Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
• 14 Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 ; Angew. Chem. 1986, 98, 504