Helvetica Chimica Acta p. 2357 - 2374 (2009)
Update date:2022-08-15
Topics:
Nishioka, Takuya
Yamamoto, Yuji
Hashino, Kimikazu
Matsumoto, Kazuko
Two chelate ligands for europium(III) having minocycline (=(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10, 12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide; 5) as a VIS-light-absorbing group were synthesized as possible VIS-light-excitable stable Eu3+ complexes for protein labeling. The 9-amino derivative 7 of minocycline was treated with H6TTHA (= triethylenetetraminehexaacetic acid=3,6,9,12-tetrakis(carboxymethyl)-3,6,9,12- tetraazatetradecanedioic acid) or H5DTPA (= diethylenetriaminepentaacetic acid=N,N-bis{2-[bis(carboxymethyl)amino]ethyl} glycine) to link the polycarboxylic acids to minocycline. One of the Eu 3+ chelates, [Eu3+(minocycline-TTHA)] (13), is moderately luminescent in H2O by excitation at 395 nm, whereas [Eu 3+(minocycline-DTPA)] (9) was not luminescent by excitation at the same wavelength. The luminescence and the excitation spectra of [Eu 3+(minocycline-TTHA)] (13) showed that, different from other luminescent EuIII chelate complexes, the emission at 615 nm is caused via direct excitation of the Eu3+ ion, and the chelate ligand is not involved in the excitation of Eu3+. However, the ligand seems to act for the prevention of quenching of the Eu3+ emission by H2O. The fact that the excitation spectrum of [Eu3+(minocycline-TTHA)] is almost identical with the absorption spectrum of Eu3+ aqua ion supports such an excitation mechanism. The high stability of the complexes of [Eu3+(minocycline-DTPA)] (9) and [Eu3+(minocycline-TTHA)] (13) was confirmed by UV-absorption semi-quantitative titrations of H 4(minocycline-DTPA) (8) and H5(minocycline-TTHA) (12) with Eu 3+. The titrations suggested also that an 1:1 ligand Eu3+ complex is formed from 12, whereas an 1:2 complex was formed from 8 minocycline-DTPA. The H5(minocycline-TTHA) (12) was successfully conjugated to streptavidin (SA) (Scheme 5), and thus the applicability of the corresponding Eu3+ complex to label a protein was established.
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