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ACS Omega
2017 Aug 10;28:4431-4439. doi: 10.1021/acsomega.7b00628.
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Stability Study of Hypervalent Tellurium Compounds in Aqueous Solutions.
Princival CR
,
Archilha MVLR
,
Dos Santos AA
,
Franco MP
,
Braga AAC
,
Rodrigues-Oliveira AF
,
Correra TC
,
Cunha RLOR
,
Comasseto JV
.
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Hypervalent tellurium compounds (telluranes) are promising therapeutical agents with negligible toxicities for some diseases in animal models. The C-Te bond of organotellurium compounds is commonly considered unstable, disfavoring their applicability in biological studies. In this study, the stability of a set of telluranes composed of an inorganic derivative and noncharged and charged organic derivatives was monitored in aqueous media with 1H, 13C, and 125Te NMR spectroscopy and high-resolution mass spectrometry. Organic telluranes were found to be remarkably resistant and stable to hydrolysis, whereas the inorganic tellurane AS101 is totally converted to the hydrolysis product, trichlorooxytellurate, [TeOCl
3
]-, which was also observed in the hydrolysis of TeCl
4
. The noteworthy stability of organotelluranes in aqueous media makes them prone to further structure-activity relationship studies and to be considered for broad biological investigations.
Scheme 1. Reported
Conversion of the Inorganic Tellurane AS101 (A) and Organic
Telluranes (B) in Aqueous Media to Hydrolysis Products
and Their 125Te Chemical Shifts
Chart 1. Structures of Studied
Telluranes
Scheme 2. Synthesis of Telluranes 8a–c, Tellurate 7, and AS101
Figure 1. (1) 125Te NMR spectrum of AS101 in DMSO-d6. (2) 125Te NMR spectrum of AS101 in DMSO-d6 and 2 equiv of
D2O. (3) 125Te NMR spectrum of AS101 in DMSO-d6 and 10 equiv of D2O. (4) 125Te NMR spectrum of TeCl4 in DMSO-d6 and 1 equiv
of D2O.
Figure 2. HRMS-ESI-(-) spectra of AS101 after treated with (A)
2 equiv and (B) 100 equiv of water.
Figure 3. (A) HRMS-ESI-(-) spectrum
of compound 7 after 30 days
in aqueous solution. (B) 125Te NMR spectrum of compound 7 in DMSO-d6. (C) 125Te NMR spectrum of compound 7 after 30 days in DMSO-d6 (300 μL) and PBS (100 μL, 1 mol/L).
Figure 4. 125Te NMR spectrum of 8a in a DMSO-d6/D2O (90:10)
mixture.
Figure 5. 125Te NMR spectrum of 8b in a DMSO-d6/D2O (90:10) mixture.
Figure 6. 125Te NMR spectrum of 8b in a DMSO-d6/D2O (90:10)
mixture.
Figure 7. 125Te NMR spectrum of 8a in a DMSO-d6/PBS buffer (pH 7.4) mixture at (A) 25 °C
after 2 h, (B) 40 °C after 48 h, and (C) 40 °C after 96
h.
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