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Journal of Inorganic Biochemistry 79 (2000) 347–351

Trends in NMR chemical shifts and ligand mobility of TcO(V) and

ReO(V) complexes with aminothiols
M. Pelecanou *, K. Chryssou, C.I. Stassinopoulou
Institute of Biology, NCSR ‘Demokritos’, POB 60228, 153 10 Athens, Greece

Received 12 May 1999; received in revised form 16 September 1999

Abstract

Detailed 1H and 13C NMR studies have been conducted in a series of oxotechnetium and oxorhenium complexes with aminothiol ligands
([SNS][S], [SNN][S], [SNNS]) designed as potential radiopharmaceuticals. The results of these studies in combination with others in
the literature show that the oxometal core creates an anisotropic environment and affects the chemical shifts of the coordinated ligand backbone
in a consistent way. Protons oriented towards the oxygen appear deshielded relative to their geminals oriented away from the oxygen. In
addition, the direction of a side chain (towards or away from the oxometal core) on the ligand backbone is shown to have a major effect on
chemical shifts. The fluxional mobility of the ligand in complexes of the [SNS][S] type was also studied by NMR and the free energy of
activation DGC/ for the conformational inversion of the ligand was calculated from the temperature dependence of the carbon chemical shifts.
DGC/ was found to depend on the orientation of the side chain present on the coordinated nitrogen. The energy barrier for the inversion is
larger for the oxorhenium complexes than for the analogous oxotechnetium complexes. q2000 Elsevier Science Inc. All rights reserved.

Keywords: Oxotechnetium complexes; Oxorhenium complexes; Nuclear magnetic resonance spectroscopy

1. Introduction rolitew) [22,23] and kidney (99mTcO-EC) [24]

radiopharmaceuticals.
This work summarizes our basic observations from the
The applications of the radioactive isotopes Tc-99m and
extensive NMR study of complexes 1, 2, and 3. Complexes
Re-186/Re-188 in nuclear medicine have prompted the inter-
of both technetium and rhenium are considered either sepa-
est for chemical studies of the two metals [1–3]. The chem-
rately or in a comparative way.
istry of technetium has many analogies with that of rhenium
due mainly to the lanthanide contraction that results in prac-
tically equal atomic radii [4].
Our team has been involved in the design, synthesis and
structural characterization of oxotechnetium(V) and oxor-
henium(V) complexes with aminothiol ligands as potential
radiopharmaceuticals [5–14]. Aminothiols are very effective
ligands for the preparation of a variety of complexes. We are
dealing primarily with complexes of two ligand types:
1. The [SNS][S] and [SNN][S] type based on the 3q1
mixed ligand concept [15–17]. This ligand system is
known for its versatility and has given promising results
especially in the area of brain radiopharmaceuticals
[5,11,18–21].
2. The [SNNS] diaminedithiol (DADT) ligand which has
given the new generation of brain (99mTcO-ECD, Neu-

* Corresponding author. Tel.: q301-650-3555; fax: q301-651-1767; e-

mail: pelmar@mail.demokritos.gr

0162-0134/00/$ - see front matter q2000 Elsevier Science Inc. All rights reserved.
PII S 0 1 6 2 - 0 1 3 4 ( 9 9 ) 0 0 2 2 7 - 5

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348 M. Pelecanou et al. / Journal of Inorganic Biochemistry 79 (2000) 347–351

Table 1
1
H and 13C chemical shifts (ppm) of the S1–C1–C2–N–C3–C4–S2 part of the ligand of representative 1a complexes in CDCl3 at 298 K

H-1 (H-4) endo H-1 (H-4) exo H-2 (H-3) endo H-2 (H-3) exo C-1 (C-4) C-2 (C-3)

MsTc
Ys4-methoxyphenyl
XsN(C2H5)2 3.59 2.96 3.61 2.81 36.96 61.38
ZsH (Ref. [6])
MsTc
Ys4-methoxyphenyl
XsSCH2CH3 3.57 2.99 3.49 2.72 36.73 61.17
ZsH (Ref. [6])
MsTc
Ysbenzyl
XsN(C2H3)2 3.85 2.24 56.64 75.22
ZsCH3 (Ref. [7])
MsTc
Ysbenzyl
Xspiperidinyl 3.90 2.24 56.66 75.15
ZsCH3 (Ref. [7])
MsRe
Ys4-methoxyphenyl
XsN(C2H5)2 3.57 2.85 3.43 2.78 42.04 62.99
ZsH (Ref. [9])
MsRe
Ys4-methylphenyl
XsN(C2H5)2 3.60 2.86 3.44 2.83 42.07 62.91
ZsH (Ref. [14])
MsRe
Ysbenzyl
Xspiperidinyl 3.86 2.24 61.58 76.31
ZsCH3 (Ref. [14])

2. Experimental In all complexes studied protons of the chelated part of the

1
H (250.13 MHz) and 13C (62.90 MHz) NMR spectra
were recorded on a Bruker AC 250E spectrometer equipped
with an Aspect 3000 computer. Samples were prepared in
CDCl3. Chemical shifts (d, ppm) are relative to TMS. Par-
ameters for the 2D spectra have been previously reported in
the literature [6–9].
For the calculation of DGC/ for conformational inversion
of the chelated rings, the coalescence temperature of the
exchanging carbon peaks and the difference in chemical shifts
in the absence of exchange were determined from tempera-
ture studies. The coalescence region for every pair of carbon
resonances under investigation was initially determined by
obtaining spectra at 5 8C intervals. Spectra were then obtained
in the coalescence region at 0.5 8C intervals to determine the
coalescence temperature Tc. The average DGC/ of three inde-
pendent determinations and the deviation from the mean
value are reported.
3. Results and discussion
3.1. Chemical shifts of complexes
Assignments of protons and carbons were based on 2D
homo- and hetero-correlation spectra and on nOe
experiments.
aminothiol ligands appear in the range dH 4.2–1.8 while cor-
responding carbons span a range of dC 75–25 [6–10]. Within
the series, the aromatic ring substituent of the monodentate
thiol has little effect on the chemical shifts of protons and
carbons of the chelated ligand backbone indicating that elec-
tronic properties of the ring are not transmitted to the chelated
part of the ligand through the metal core. Similarly, no effect
is recorded on the chemical shifts of the ligand substituent
upon variation of the substituent X.
NMR studies of a series of complexes of the 3q1
[SNS][S] mixed ligand type having the free chain on the
nitrogen in the syn configuration (complex 1a), showed that
geminal protons as well as geminal methyl groups on the S1–
C1–C2–N–C3–C4–S2 chelated part of the ligand are differ-
entiated according to their vicinity to the oxometal core
(Table 1). Distinction of endo (close to the oxygen) versus
exo (away from the oxygen) position was based on the exis-
tence of nOe cross peaks between the protons of the pendant
chain on the nitrogen, known from crystallographic data to
be in the syn configuration (towards oxygen), and protons
of the chelated ligand backbone. Under the same reasoning,
when ZsCH3 the methyl groups exhibiting nOe peaks with
the pendant chain were assigned as endo. In complexes of
type 1a endo protons or endo methyl groups appear consis-
tently at higher frequencies than the corresponding exo. The

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 M. Pelecanou et al. / Journal of Inorganic Biochemistry 79 (2000) 347–351
observed differences between endo and exo proton chemical
shifts in this type of complexes range from 1.7 to 0.2 ppm.
When ZsCH3 the observed difference between endo and exo
methyl groups is 0.4 ppm [7].
This distinction of endo and exo protons, which was based
on solid experimental evidence, was also applied in the case
of the [SNN][S] ligand system (complex 2), in which the
central nitrogen lacks a side chain and no informative nOe
correlations can be obtained. It was found valid since it led
to internally consistent nOe connectivities [8]. Our experi-
mental data demonstrate that it can safely be extended in the
case of the 3q1 [SSS][S] complex where again no pendant
chain is present [25]. In addition, detailed assignment of the
oxorhenium complex with the related diaminedithiol
(DADT) ligand (complex 4) showed that endo protons and
methyl groups on the chelated ligand backbone follow the
trend and appear at higher frequencies than their exo geminals
with a Dd(endo–exo) ranging from 0.3 to 1 ppm [12]. NMR
data found in the literature on oxotechnetium and oxorhenium
complexes with diaminedithiol [26–32], diamidodithiol
[33], or monoamine-monoamido dithiol [34] ligands show
similar differentiations in the chemical shifts of geminal pro-
tons or groups on the chelated backbone; however, distinction
of exo and endo protons is not made in all cases.
A first application of the differentiation of proton chemical
shifts according to their proximity to the oxometal core is the
distinction of diastereomers in the case where a pendant group
is present that can have the syn (towards oxygen) or anti
(away from oxygen) configuration. Specifically, in the case
of the complex 1a (MsRe, ZsH, Ys4-methoxyphenyl,
XsN(C2H5)2) methylene protons of the pendant chain close
to the coordinated nitrogen appear as one multiplet at 3.92
ppm, while the corresponding protons of its anti isomer 1b
appear as closely spaced multiplets at 2.35 and 2.25 ppm [9].
Other examples in the literature with similar ligands bearing
pendant groups on nitrogen reinforce the argument that it is
possible to assign the stereochemistry of the chain based
exclusively on NMR data. Thus, in the N-ethyl-diaminedi-
thiol oxotechnetate, the diastereotopic methylene protons of
the N-ethyl substituent in the syn isomer 4a appear as two
multiplets in a deshielded environment, at 4.1 and 3.9 ppm,
while in the anti isomer 4b the methylene protons are shifted
upfield at 2.7 and 1.5 ppm [30]. In the related system of
monoamine monoamide dithiol bearing a N-benzyl substit-
uent, the benzylic methylene protons associated with the syn
diastereomer 5a resonate at 5.1 and 4.7 ppm, while the cor-
responding protons of the anti diastereomer 5b show signif-
icant upfield shifts to 3.4 and 2.7 ppm [33]. Detection of
diastereomers from NMR data is also possible when the pen-
dant group is on a carbon of the chelated ligand instead of a
nitrogen [27,34]. For example, in the case of the syn isomer
of the diamide dithiol complex 6a, the diastereotopic protons
of the methylene group noted with an asterisk appear at 1.8
and 2.3 ppm, while those of the anti isomer 6b are upfield at
1.2 and 1.5 ppm [34].
Friday Apr 07 11:06 AM
349
The chemical shifts of the carbons of the pendant chain are
influenced by the proximity to the oxometal core as well and
can be used to assign syn or anti configuration. In complex
1a (MsRe, ZsH, Ys4-methoxyphenyl, XsN(C2H5)2)
the carbon close to coordinated nitrogen appears at 61.3 ppm,
while in the anti isomer it appears at 50.5 ppm [9]. A
Dd(syn–anti) of 5.8 ppm is recorded for the methylene car-
bon of complexes 5a and 5b [33] and a Dd(syn–anti) of 4
ppm for the ethylene carbon noted with an asterisk in com-
plexes 6a and 6b [34].
The differentiation in chemical shifts of endo versus exo
chemical shifts of the atoms on the chelated backbone is
commonly attributed in the literature to the anisotropic envi-
ronment created by the oxometal core [27,32,33]. Our exper-
imental data show that, in addition to the oxometal core, other
factors such as chemical bond anisotropies are contributing
to the observed exo/endo differentiation. For example, evi-
dence for the key role played by the direction of the pendant
chain on the chemical shifts of the protons of the chelated
S1–C1–C2–N–C3–C4–S2 part of the ligand is given by our
detailed chemical shift assignments of the diastereomeric
complexes 1a and 1b (MsRe, Ys4-methoxyphenyl, ZsH,
XsN(C2H5)2) [9]. While the syn isomer displays the usual
exo/endo differentiation, in the anti isomer the endo and exo
protons close to sulfur are lumped together and the exo pro-
tons close to nitrogen appear more deshielded than the endo.
This deviation from the commonly observed trend, according
to which endo protons appear downfield compared to exo,
clearly indicates that the magnetic anisotropies of the bonds
and atoms of the side chain are influencing the chemical shifts
of the ligand backbone. One should also consider the different
crystal geometries of the isomers (the syn isomer is a distorted
trigonal bipyramid with oxygen situated in the basal plane
whereas the anti isomer is a square pyramid with the oxygen
occupying the apical position [9]) which may define differ-
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350 M. Pelecanou et al. / Journal of Inorganic Biochemistry 79 (2000) 347–351

ent shielding topologies. Evidence that the electrostatic field

of the lone pairs of the sulfur may be contributing to the
observed anisotropies is provided by our studies of complexes
of the [SNN][S] type [8].
Comparative NMR data [14]on homologous Tc_O and
Re_O complexes of the syn configuration (complex 1a)
show lack of metal dependence of the proton chemical shifts.
The observed differences DdH(Re–Tc) range from "0.01 to
0.3 ppm and cannot be associated with specific positions in
the molecule. On the contrary, the 13C data show metal
dependence. Specifically, carbons adjacent to a coordinated
atom are more deshielded in rhenium than in technetium
complexes. In a number of complexes of type 1a studied
[14] the difference DdC (Re–Tc) for the carbons that are
adjacent to a coordinated sulfur atom ranges from 4.9 to 6.8
ppm. DdC (Re–Tc) for the carbons that are adjacent to a
coordinated nitrogen ranges from 1.0 to 2.4 ppm. This effect
is also present in the NMR data reported for homologous
technetium and rhenium diaminedithiol [27] and diamide
dithiol [34] complexes. In agreement with our observations
no significant dependence of proton chemical shifts on the
metal can be observed in the literature reported data.

3.2. Ligand mobility in the complexes
The fluxional conformational mobility of the two five-
membered rings –M–S1–C1–C2–N– and –M–N–C3–C4–
S2– formed by the chelated parts of the ligand in complexes
1a and 1b was studied by NMR. When interconversion of all
possible conformers is fast on the NMR time scale an effec-
tive plane of symmetry is generated passing through the M–
O–N atoms. As a result, protons and carbons on the
exchanging parts S1–C1–C2–N and N–C3–C4–S become
magnetically equivalent and an average spectrum of all pos-
sible conformations is obtained. When the conformational
motion is slower, exchanging protons and carbons on S1–
C1–C2–N and N–C3–C4–N appear either as broad peaks
(intermediate rate of exchange) or as separate spin systems
(slow exchange).
Calculation of DGC/ for the conformational inversion of
the chelated rings was based on the temperature dependence
of the carbon spectra. Fig. 1 displays the temperature depend-
ence of the 13C spectra of complex 1a (MsRe, ZsH, Ys4-
methoxyphenyl, XsN(C2H5)2). Exchanging carbons C1/
C4 and C2/C3 appear as two separate peaks at slow
exchange, they coalesce as the temperature is raised, and
become one sharp peak in fast exchange. The conformational
inversion barrier for the technetium complex 1a (MsTc,
ZsH, Ys4-methoxyphenyl, XsN(C2H5)2) was found to
be 12.0"0.1 kcal/mol, while the corresponding rhenium
complex gave a DGC/ of 13.7"0.1 kcal/mol [9]. The dif-
ference in DGC/ indicates that Tc_O complexes are more
flexible than their Re_O analogues. This fact is also reflected
in the appearance of the 1H NMR spectra where the Tc_O
complexes give, at room temperature, sharp average spectra
while their Re_O analogues give broad unresolved peaks.
Fig. 1. Temperature dependence of the 13C NMR spectra of complex 1a
(MsRe, ZsH, Ys4-methoxyphenyl, XsN(C2H5)2). At 253 K exchang-
ing carbons C-1/C-4 and C-2/C-3 appear as separate peaks. As the temper-
ature is raised the peaks coalesce and finally give rise to sharp averaged
peaks.
The difference in conformational flexibility is an observation
that adds to the differences in physicochemical properties
recorded between homologous Tc and Re complexes of this
type, such as the metal–oxygen stretching vibration and the
oxidation–reduction potential [14].
Two more oxorhenium complexes of the type 1a studied
for comparison purposes gave DGC/ values of 13.8"0.1
kcal/mol (ZsH, Ys4-methylphenyl, XsN(C2H5)2) and
13.4"0.1 kcal/mol (ZsCH3, Ysbenzyl, Xspiperidinyl).
Comparison of the three values of DGC/ reported above for
the oxorhenium complexes of type 1a indicates that minor
structural changes such as the presence of methyl groups on
the ligand backbone, different substituents on the N-side
chain, or different para-substituents on the aromatic thiol, do
not affect appreciably the mobility of the ligand. However,
when the aromatic thiol coligand is replaced by a smaller
group the complex becomes more flexible. Specifically, when
the thiol group is replaced by a chlorine, the complex gives
sharp 1H and 13C resonances at room temperature and no
significant change is observed in the spectra down to 223 K.
Fluxional mobility is appreciably influenced by the direc-
tion of the free chain on the nitrogen. DGC/ of activation for
the anti isomer (1b, MsRe, ZsH, Ys4-methoxyphenyl,
XsN(C2H5)2) is 15.9"0.1 kcal/mol compared to the
13.7"0.1 kcal/mol for the syn analogue given above [9].
As a result, in CDCl3 at 298 K conformational inversion for
the syn isomer is 36 times faster than that of the anti. As
expected, the difference in mobility is reflected in the appear-

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 M. Pelecanou et al. / Journal of Inorganic Biochemistry 79 (2000) 347–351
ance of the spectrum of the anti isomer which at room tem-
perature is in the slow region of exchange and provides,
besides the differentiation in chemical shifts, an alternative
way for the easy distinction of syn–anti diastereomers.
4. Concluding remarks
It is generally accepted by now in the field of nuclear
medicine that detailed structural data on potential radiophar-
maceuticals are essential to lay a strong foundation for assess-
ment of biological and clinical studies and to establish valid
structure/function relationships. NMR studies, in addition to
being a powerful analytical tool are also providing a wealth
of information on stability, stereochemistry, interconversion,
ease of protonation and conformational mobility. These prop-
erties are related to the fate of a pharmaceutical in the recipient
patient and/or experimental animal, the biodistribution, and
the retention in a specific tissue. For example, the easy dis-
tinction of diastereomers 1a and 1b provided by NMR may
have a practical application since the syn isomer (Ms99mTc,
ZsH, Ys4-methoxyphenyl, XsN(C2H5)2) displays
higher brain/blood values and prolonged retention in the
brain compared to the anti [5]. The detailed study of the
interconversions of the methylated ReO-ECD in aqueous
solution [26] provides another example for the insight
offered by NMR on the in vivo structure of a radiopharma-
ceutical. NMR is also a very powerful tool for the study of
the interaction of oxotechnetium and oxorhenium complexes
with biomolecules that may play a role in their uptake and
biodistribution, as was recently demonstrated in the NMR
study of the interaction of complex 1a (MsRe, ZsH, Ys4-
methoxyphenyl, XsN(C2H5)2) with glutathione [13].
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