Synthesis, Relaxation Properties and In vivo Assessment of Carborane-GdDOTA-Monoamide Conjugate as MRI Blood Pool Contrast Agent
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Synthesis, Relaxation Properties and In vivo Assessment of Carborane-GdDTA-Monoamide Conjugate as MRI Blood Pool Contrast Agent Lalit. Goswami, Quanyu Cai, Lixin Ma, Satish S. Jalisatgi and M. Frederick awthorne* International Institute of ano and Molecular Medicine, School of Medicine, University of Missouri, Columbia, M , USA *Author to whom correspondence should be addressed. hawthornem@missouri.edu; Tel.: ; Fax: Contents: 1. Copies of MR, and RMS spectrums of compounds 1, 2, 3, 4, CB-GdDTA-MA & CB-DyDTA-MA. 2. Fig. S1: IR spectrums of 4 & CB-GdDTA-MA. 3. Fig. S2: PLC trace of CB-GdDTA-MA. 4. Fig. S3: Determination of ydration number (q) for CB-DyDTA-MA. 5. Fig. S4: Representative in vivo T1-weighted MRA scans of a mouse at various time points p.i. of mniscan. 1
2 B a) C 2 tbu C 2 tbu 6,9-(Et 2 S) 2 B Br + b) c) Br tbu 2 C =B =C =C d) - Gd ( 2 ) n e) f) - Dy 3+ - ( 2 ) n - CB-GdDTA-MA 4 CB-DyDTA-MA Scheme 1 Synthesis of CB-GdDTA-MA. Reagents and conditions: a) Et 2 S, Toluene, 85 C, 2 h. b) Acetonitrile, 65 C, 12 h, 41%. c) D3A-t-Bu-ester,, -diisopropylethylamine, 85 C for 12 h, 60%. d) Formic acid, 60 C, 12 h, 82%. e) GdCl 3.6 2, 2 -Me (1:1), p 6.5, RT, 12 h, 73%. f) DyCl 3.6 2, 2 -Me (1:1), p 6.5, RT, 12 h, 68%. 2
3 ppm
4 ppm
5 [M+a] + Br 1 RMS 5
6 ppm
7 ppm
8 ppm
9 [M+Br] Br 2 RMS [M] [M+2Br] 9
10 C 2 tbu C 2 tbu tbu 2 C 3 1 MR, CDCl3, 400 Mz ppm
11 C 2 tbu C 2 tbu tbu 2 C 3 13 CMR, CDCl3, Mz ppm
12 C 2 tbu C 2 tbu tbu 2 C 3 11 B MR (dc), CDCl 3, 128 Mz ppm
13 [M+a] + C 2 tbu C 2 tbu tbu 2 C 3 RMS 13
14 C 2 C 2 2 C 4 1 MR,CD3 D, 500 Mz ppm
15 C 2 C 2 2 C 4 13 CMR,CD3 D, 125 Mz AC AC ppm
16 C 2 C 2 2 C 4 11 BMR,CD 3 D, 160 Mz ppm
17 [M ] C 2 C 2 2 C 4 RMS 17
18 - Gd ( 2 ) n CB-GdDTA-MA Chemical Formula: C B 10 Gd 5 7 Molecular Weight: [M ] 18
19 [M+] + [M+2] 2+ - Dy ( 2 ) n CB-DyDTA-MA Chemical Formula: C B 10 Dy 5 7 Molecular Weight: [M+3] 3+ [4M+3] 3+ [3M+2] 2+ [2M+] + 19
20 C 2 60 C 2 50 CB DTA C CB GdDTA MA 2 C 4 (CB-DTA-C) % Transmittance C Wavenumber (cm 1) Fig. S1 IR spectrums of compound 4 and CB GdDTA MA. 500 SATI 1.00 Analytical PLC analysis of CB-GdDTA-MA Instrument: Alliance Waters Column: Agilent Zorbax SB-C18, 5 μm (4.6 x 250 mm). Eluent: 1 ml/min; gradient: B 0% to 100% over 45 min, B 100% min (A: water, B: acetonitrile). Detector: Evaporative Scattering Detector (SEDEX 75, operated at 45 C and 3.5 bars using 2 ). mv Minutes Fig. S2 PLC trace of CB GdDTA MA. 20
21 Dy 3+ -Induced 17 MR shift (ppm) Dy 3+ -Induced 17 MR Shift DyCl3.62 CB-DyDTA-MA y = x R² = 1 y = x R² = Conc. (mm) Determination of hydration number (q) for CB-DyDTA-MA: Varying concentrations of CB-DyDTA-MA and DyCl over the range mmol dm -3 were prepared in 80% D 2-2 and the p of the solutions was adjusted to p 7.0. The 17 MR experiments were performed using a Bruker Ascend 400 Mz MR instrument at RT with the deuterium signal locked. A graph was plotted between the Δδ and the concentration for both CB- DyDTA-MA and the DyCl solutions and slope was obtained. The Δδ value for a complex with the general formula, Dy(ligand) n ( 2 ) q, is given by the following relation; (Δδ) = qδ[dy(ligand) n ( 2 ) q ]/[ 2 ] (I) The slope of a plot of the Δδ versus the Dy 3+ concentration is proportional to the q value of the complex (Figure). The q value was obtained by linearly fitting the Δδ value and was found to be 2 for complex CB-DyDTA-MA. From the graph, which fit well to a straight line, the slope was calculated. From relation I, the slope of the graph can be equated with the following; Slope = qδ/[2], From the graph, the slope was calculated as, Slope = -381 ppm dm 3 mol -1 or, qδ/[2] = -381 ppm dm 3 mol -1 For DyCl 3, the value of q was assumed to be 9, because the coordination number of Dy(III) in such complexes known to be 9. ence, the value of Δ/[2] is calculated as follows: Δ/[2] = -381 ppm dm 3 mol -1 /9 or Δ/[2] = ppm dm 3 mol -1 From this calculation, a value of q for the DTA-Dy 3+ complex CB-DyDTA-MA is calculated as follows: For complex CB-DyDTA-MA, Slope = qδ/[2], or q = slope/(δ/[2]) or q = -50.4/-42.3, hence q = 1.2 Fig. S3 Determination of ydration number (q) for CB-DyDTA-MA. 21
22 Pre 16s 1min 5min 10min 30min 1h Fig. S4 Representative in vivo T1-weighted MRA scans of a mouse at various time points p.i. of mniscan at a Gd dose of 1.2 mmol/kg. 3h 22
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