Inorganic Chemistry
Forum Article
(17) Loh, C.-T.; Graham, B.; Abdelkader, E. H.; Tuck, K. L.; Otting,
G. Generation of pseudocontact shifts in proteins with lanthanides
using small “clickable” nitrilotriacetic acid and iminodiacetic acid tags.
Chem. - Eur. J. 2015, 21, 5084−5092.
(18) Loh, C. T.; Ozawa, K.; Tuck, K. L.; Barlow, N.; Huber, T.;
Otting, G.; Graham, B. Lanthanide tags for site-specific ligation to an
unnatural amino acid and generation of pseudocontact shifts in
proteins. Bioconjugate Chem. 2013, 24, 260−268.
AUTHOR INFORMATION
Corresponding Author
■
ORCID
Notes
The authors declare no competing financial interest.
(19) Aulsebrook, M. L.; Starck, M.; Grace, M. R.; Graham, B.;
Thordarson, P.; Pal, R.; Tuck, K. L. Interaction of nucleotides with a
trinuclear terbium(III)-dizinc(II) complex: efficient sensitization of
terbium luminescence by guanosine monophosphate and application
to real-time monitoring of phosphodiesterase activity. Inorg. Chem.
2019, 58, 495−505.
ACKNOWLEDGMENTS
The authors acknowledge support from the School of
Chemistry, Monash University.
■
(20) (a) Isaac, M.; Raibaut, L.; Cepeda, C.; Roux, A.; Boturyn, D.;
REFERENCES
́
̀
Eliseeva, S. V.; Petoud, S.; Seneque, O. Luminescent zinc fingers: Zn-
responsive neodymium near-infrared emission in water. Chem. - Eur. J.
2017, 23, 10992−10996. (b) Isaac, M.; Pallier, A.; Szeremeta, F.;
■
(1) Aulsebrook, M. L.; Graham, B.; Grace, M. R.; Tuck, K. L.
Lanthanide complexes for luminescence-based sensing of low
molecular weight analytes. Coord. Chem. Rev. 2018, 375, 191−220.
(2) Thibon, A.; Pierre, V. C. Principles of responsive lanthanide-
based luminescent probes for cellular imaging. Anal. Bioanal. Chem.
2009, 394, 107−20.
(3) Shuvaev, S.; Starck, M.; Parker, D. Responsive, water-soluble
europium(III) luminescent probes. Chem. - Eur. J. 2017, 23, 9974−
9989.
(4) Butler, S. J.; Parker, D. Anion binding in water at lanthanide
centres: from structure and selectivity to signalling and sensing. Chem.
Soc. Rev. 2013, 42, 1652−1666.
(5) Aletti, A. B.; Gillen, D. M.; Gunnlaugsson, T. Luminescent/
colorimetric probes and (chemo-) sensors for detecting anions based
on transition and lanthanide ion receptor/binding complexes. Coord.
Chem. Rev. 2018, 354, 98−120.
(6) Sabbatini, N.; Guardigli, M.; Lehn, J. M. Luminescent lanthanide
complexes as photochemical supramolecular devices. Coord. Chem.
Rev. 1993, 123, 201.
(7) Beeby, A.; Faulkner, S.; Parker, D.; Williams, J. G. Sensitised
luminescence from phenanthridine appended lanthanide complexes:
analysis of triplet mediated energy transfer processes in terbium,
europium and neodymium complexes. J. Chem. Soc., Perkin Trans. 2
2001, 8, 1268−1273.
(8) Evans, C. H. Biochemistry of the Lanthanides; Springer Science &
Business Media, 2013; Vol. 8.
̈
(9) Gschneidner, K. A.; Bunzli, J.-C. G.; Pecharsky, V. K. Handbook
on the physics and chemistry of rare earths: optical spectroscopy; Elsevier,
2011; Vol. 37.
(10) Hu, W.; Bai, F.; Gong, X.; Zhan, X.; Fu, H.; Bjornholm, T.
Organic optoelectronics; John Wiley & Sons, 2012.
(11) Samuel, A. P. S. Optimizing new classes of luminescent lanthanide
complexes; ProQuest, 2008.
(12) Aulsebrook, M. L.; Graham, B.; Grace, M. R.; Tuck, K. L. The
synthesis of luminescent lanthanide-based chemosensors for the
detection of zinc ions. Tetrahedron 2014, 70, 4367−4372.
(13) Thorson, M. K.; Ung, P.; Leaver, F. M.; Corbin, T. S.; Tuck, K.
L.; Graham, B.; Barrios, A. M. Lanthanide complexes as luminogenic
probes to measure sulfide levels in industrial samples. Anal. Chim.
Acta 2015, 896, 160−165.
(14) O’Malley, W. I.; Abdelkader, E. H.; Aulsebrook, M. L.;
Rubbiani, R.; Loh, C.-T.; Grace, M. R.; Spiccia, L.; Gasser, G.; Otting,
G.; Tuck, K. L.; Graham, B. Luminescent alkyne-bearing terbium (III)
complexes and their application to bioorthogonal protein labeling.
Inorg. Chem. 2016, 55, 1674−1682.
(15) O’Malley, W. I.; Rubbiani, R.; Aulsebrook, M. L.; Grace, M. R.;
Spiccia, L.; Tuck, K. L.; Gasser, G.; Graham, B. Cellular uptake and
photo-cytotoxicity of a gadolinium(III)-DOTA-naphthalimide com-
plex “clicked” to a lipidated tat peptide. Molecules 2016, 21, 194.
(16) Aulsebrook, M. L.; Biswas, S.; Leaver, F. M.; Grace, M. R.;
Graham, B.; Barrios, A. M.; Tuck, K. L. A luminogenic lanthanide-
based probe for the highly selective detection of nanomolar sulfide
levels in aqueous samples. Chem. Commun. 2017, 53, 4911−4914.
́
̀
Bayle, P.-A.; Barantin, L.; Bonnet, C. S.; Seneque, O. MRI and
luminescence detection of Zn2+ with a lanthanide complex-zinc finger
peptide conjugate. Chem. Commun. 2018, 54, 7350−7353. (c) Gunn-
laugsson, T.; Harte, A. J.; Leonard, J. P.; Nieuwenhuyzen, M. The
Formation of Luminescent Supramolecular Ternary Complexes in
Water: Delayed Luminescence Sensing of Aromatic Carboxylates
Using Coordinated Unsaturated Cationic Heptadentate Lanthanide
Ion Complexes. Supramol. Chem. 2003, 15, 505−519. (d) Esplin, T.
L.; Cable, M. L.; Gray, H. B.; Ponce, A. Terbium-Macrocycle
Complexes as Chemical Sensors: Detection of an Aspirin Metabolite
in Urine Using a Salicylurate-Specific Receptor Site. Inorg. Chem.
2010, 49, 4643−4647.
(21) Lee, A. E.; Grace, M. R.; Meyer, A. G.; Tuck, K. L. Fluorescent
Zn2+ chemosensors, functional in aqueous solution under environ-
mentally relevant conditions. Tetrahedron Lett. 2010, 51, 1161−1165.
(22) Aulsebrook, M. L.; Graham, B.; Grace, M. R.; Tuck, K. L.
Coumarin-based fluorescent sensors for zinc(II) and hypochlorite.
Supramol. Chem. 2015, 27, 798−806.
(23) Vallee, B. L.; Falchuk, K. H. The biochemical basis of zinc
physiology. Physiol. Rev. 1993, 73, 79−118.
(24) Ye, Z.; Xiao, Y.; Song, B.; Yuan, J. Design and synthesis of a
new terbium complex-based luminescent probe for time-resolved
luminescence sensing of zinc ions. J. Fluoresc. 2014, 24, 1537−1544.
(25) Ye, Z.; Wang, G.; Chen, J.; Fu, X.; Zhang, W.; Yuan, J.
Development of a novel terbium chelate-based luminescent chemo-
sensor for time-resolved luminescence detection of intracellular Zn2+
ions. Biosens. Bioelectron. 2010, 26, 1043−1048.
(26) Roger, M.; Regueiro-Figueroa, M.; Ben Azzeddine, C.; Patinec,
V.; Bonnet, C. S.; Platas-Iglesias, C.; Tripier, R. Lanthanide complexes
with heteroditopic ligands as fluorescent zinc sensors. Eur. J. Inorg.
Chem. 2014, 2014, 1072−1081.
(27) Comby, S.; Tuck, S. A.; Truman, L. K.; Kotova, O.;
Gunnlaugsson, T. New trick for an old ligand! The sensing of Zn(II)
using a lanthanide based ternary Yb(III)-cyclen-8-hydroxyquinoline
system as a dual emissive probe for displacement assay. Inorg. Chem.
2012, 51, 10158−10168.
(28) Matsubara, T.; Hirao, K. Density functional study of the
binding of the cyclen-coordinated M (II)(M= Zn, Cu, Ni) complexes
to the DNA base. Why is Zn better to bind? J. Mol. Struct.:
THEOCHEM 2002, 581, 203−213.
(29) Han, M. S.; Kim, D. H. Readily available fluorescence probes
for zinc ion in aqueous solution of neutral pH. Supramol. Chem. 2003,
15, 59−64.
(30) Beeby, A.; Clarkson, I. M.; Dickins, R. S.; Faulkner, S.; Parker,
D.; Royle, L.; de Sousa, A. S.; Williams, J. A. G.; Woods, M. Non-
radiative deactivation of the excited states of europium, terbium and
ytterbium complexes by proximate energy-matched OH, NH and CH
oscillators: an improved luminescence method for establishing
solution hydration states. J. Chem. Soc., Perkin Trans. 2 1999, 3,
493−504.
I
Inorg. Chem. XXXX, XXX, XXX−XXX