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Preliminary evaluation of PARACEST MRI agents for the detection of nitric oxide synthase (NOS)
Mojmír Suchý,a.b Alex X. Li,b Yin Liu,c Qingping Feng,c Robert Bartha,b and Robert H. E. Hudson*a,d
aDepartment of Chemistry and dThe Centre for Advanced Materials and Biomaterials
Research, The University of Western Ontario, London, Ontario, Canada, N6A 5B7
b Robarts Research Institute, The University of Western Ontario, London, Ontario,
Canada, N6A 5K8
cDepartment of Physiology and Pharmacology, The University of Western Ontario,
London, Ontario, Canada, N6A 5C1
E-mail: [email protected] Tel: 519-661-2111 ext. 86349 Fax: 519-661-3022
(ELECTRONIC SUPPLEMENTARY INFORMATION)
SI1
CONTENTS1H and 13C NMR spectra of 9, 10a and 10b......................................................................SI31H NMR spectra of DOTAM-Cit-OMe and DOTAM-Gly-Cit-OMe...............................SI9
HR-ESI-MS spectra of DOTAM-Cit-OMe, DOTAM-Gly-Cit-OMe, 11, 12a and 12b...SI11
HPLC chromatograms of the reaction mixtures containing DOTAM-Cit-OMe and DOTAM-
Gly-Cit-OMe.....................................................................................................................SI16
UPLC traces of purified complexes Dy3+DOTAM-Cit-OH, Dy3+DOTAM-Gly-Cit-OH and
Tm3+DOTAM-Gly-Cit-OH................................................................................................SI17
SI2
Figure SI1: 1H NMR spectrum of L-Cit-OMe · HCl (9) in D2O
SI3
Figure SI2: 13C NMR spectrum of L-Cit-OMe · HCl (9) in D2O
SI4
Figure SI3: 1H NMR spectrum of N-chloroacetyl-Cit-OMe (10a) in DMSO-D6
SI5
3.63
water
Figure SI4: 13C NMR spectrum of N-chloroacetyl-Cit-OMe (10a) in DMSO-D6
SI6
Figure SI5: 1H NMR spectrum of N-chloroacetyl-Gly-Cit-OMe (10b) in DMSO-D6
SI7
3.62
water
Figure SI6: 13C NMR spectrum of N-chloroacetyl-Gly-Cit-OMe (10b) in DMSO-D6
SI8
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Figure SI7: 1H NMR spectrum of the free ligand DOTAM-Cit-OMe in DMSO-D6
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3.62
water
Figure SI8: 1H NMR spectrum of the free ligand DOTAM-Gly-Cit-OMe in DMSO-D6
SI11
3.62
Figure SI9: HR-ESI-MS spectrum of DOTAM-Cit-OMe, note the charge state envelope 1089.6 (M+), 545.3 (M2+)
Figure SI10: HR-ESI-MS spectrum of DOTAM-Cit-OMe, expanded view of 1089.6 (M+) charge state, observed (bottom), simulated (top)
SI12
Figure SI11: HR-ESI-MS spectrum of DOTAM-Gly-Cit-OMe, note the charge state envelope 1317.6 (M+), 659.3 (M2+), 439.9 (M3+)
Figure SI12: HR-ESI-MS spectrum of DOTAM-Gly-Cit-OMe, expanded view of 1317.6 (M+) charge state, observed (bottom), simulated (top)
SI13
Figure SI13: HR-ESI-MS spectrum of Dy3+ DOTAM-Cit-OH (7), note the charge state envelope 1192.4 (M+), 597.7 (M2+), 398.8 (M3+)
Figure SI14: HR-ESI-MS spectrum of Dy3+ DOTAM-Cit-OH (7), expanded view of 597.7 (M2+) charge state, observed (bottom), simulated (top)
SI14
Figure SI15: HR-ESI-MS spectrum of Dy3+ DOTAM-Gly-Cit-OH (8a), note the charge state envelope 1421.5 (M+), 711.7 (M2+), 474.8 (M3+)
Figure SI16: HR-ESI-MS spectrum of Dy3+ DOTAM-Gly-Cit-OH (8a), expanded view of 711.8 (M2+) charge state, observed (bottom), simulated (top)
SI15
Figure SI17: HR-ESI-MS spectrum of Tm3+ DOTAM-Gly-Cit-OH (8b), note the proper charge state envelope 1427.5 (M+), 714.2 (M2+), 476.5 (M3+)
Figure SI18: HR-ESI-MS spectrum of Tm3+ DOTAM-Gly-Cit-OH (8b), expanded view of 714.3 (M2+) charge state, observed (bottom), simulated (top)
SI16
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Figure SI19: HPLC chromatogram (Method A) of the mixture containing DOTAM-Cit-OMe (tR 5.4 min)
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Figure SI20: HPLC chromatogram (Method A) of the mixture containing DOTAM-Gly-Cit-OMe (tR 4.3 min).
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Figure SI21. UPLC trace of Dy3+DOTAM-Cit-OH, 7, UV monitoring at = 220 nm.
Figure SI22. UPLC trace of Dy3+DOTAM-Gly-Cit-OH, 8a, UV monitoring at = 220 nm.
Figure SI22. Tm3+DOTAM-Gly-Cit-OH, 8b, UV monitoring at = 220 nm.
SI18