J Incl Phenom Macrocycl Chem
Preparation of compound 5
2. Czarnik, A.W.: Chemical communication in water using fluo-
rescent chemosensors. Acc. Chem. Res. 27, 302–308 (1994)
3
. Kim, J.S., Quang, D.T.: Calixarene-derived fluorescent probes.
Chem. Rev. 107, 3780–3799 (2007)
4. Xu, Z., Yoon, J., Spring, D.R.: Fluorescent chemosensors for
N-alkylation of compound 3 (1.56 gm, 5 mmol) with t-butyl
bromoacetate 4 (1.46 ml, 10 mmol) was carried out under
DMF/K CO condition. The reaction mixture was stirred at
2?
Zn . Chem. Soc. Rev. 39, 1996–2006 (2010)
2
3
5
. Que, E.L., Domaille, D.W., Chang, C.J.: Metals in neurobiology:
probing their chemistry and biology with molecular imaging.
Chem. Rev. 108, 1517–1549 (2008)
room temperature for 24 h, whereby the TLC indicated
complete conversion. The reaction mixture was then poured
in water; solid obtained was filtered, washed with water and
6. Vallee, B.L., Falchuk, K.H.: The biochemical basis of zinc
physiology. Physiol. Rev. 73, 79–118 (1993)
air dried. Crystallization from CHCl : EtOH (95:5 v/v)
3
0
0
7. Lippard, S.J., Berg, J.M.: Principles of bioinorganic chemistry.
University Science Books, Mill Valley (1994)
afforded the desired, tert-butyl-2,2 -(2,2 -(pyridine-2,6-
1
diyl)bis( H-benzo[d]imidazole-2,1diyl)) diacetate 5 in 76 %
8
. Cuajungco, M.P., Lees, G.J.: Zinc metabolism in the brain: rel-
evance to human neurodegenerative disorders. Neurobiol. Disord.
4, 137–169 (1997)
-
1
yield (2.052 gm), mp 161–163 °C. IR (KBr, cm ): 3057,
972, 1744, 1593, 1456, 1430, 1375, 1333, 1231, 1155, 748.
2
1
9. Hardy, J.: Has the amyloid cascade hypothesis for Alzheimers
disease been proved? Curr. Alzheimer Res. 3, 71–73 (2006)
0. Burdette, S.C., Walkup, G.K., Spingler, B., Tsein, R.Y., Lippard,
H NMR (300 MHz, CDCl ): d 1.16 (s, 18H), 5.37 (s, 4H),
3
1
7
.41 (m, 6H), 7.91 (dd, 2H, J = 3.0, 5.0 Hz), 8.08 (t, H,
J = 5.1), 8.48 (d, 2H, J = 7.8 Hz). Elemental analysiscalcd.
for C H N O : C, 69.00; H, 6.16; N, 12.98. Found: C,
1
2?
S.J.: Fluorescent sensors for Zn based in fluorescein platform:
synthesis, properties and intracellular distribution. J. Am. Chem.
Soc. 123, 7831–7841 (2001)
3
1 33 5 4
6
9.15; H, 6.12; N, 12.85.
1
1. Kimura, E., Aoki, S.: Chemistry of zinc(II) fluorophore sensors.
Biometals 14, 191–204 (2001)
Preparation of target probe, Dibcid
12. Lakshmi, C., Hanshaw, R.G., Smith, B.D.: Fluorophore-linked
zinc(II)dipicolylamine coordination complexes as sensors for
phosphatidylserine-containing membranes. Tetrahedron 60,
Product 5 (0.539 g, 1 mmol) was added to a solution of
dioxane (10 ml) containing 1 ml of 50 % HCl. The reaction
mixture was heated at 70–80 °C for 4 h, and then it was
worked up by diluting with water. The precipitated solid was
filtered, washed with water and air dried. This target mole-
cule Dibcid was obtained in 56 % yield (0.239 g),
1
1307–11315 (2004)
1
1
3. Jiang, P., Guo, Z.: Fluorescent detection of zinc in biological
systems: recent development on the design of chemosensors and
biosensors. Coord. Chem. Rev. 248, 205–229 (2004)
4. Rurack, K., Bricks, J.L., Reck, G., Radeglia, R., Resch-Genger,
U.: Chalcone-analogue dyes emitting in the near-infrared (NIR):
influence of donor–acceptor substitution and cation complexation
on their spectroscopic properties and X-ray structure. J. Phys.
Chem. A 104, 3087–3109 (2000)
-
1
mp [ 251 °C. IR (KBr, cm ): 3300–2500 broad band,
1
720, 1629, 1459, 1377, 1231, 1176, 893, 832, 749. H NMR
1
1
1
5. Haugland, R.P.: Handbook of fluorescent probes and research
products, 9th edn. Molecular Probes, Inc., Eugene (2002)
6. Fahrni, C.J., O’Halloran, T.V.: Aqueous coordination chemistry
of quinoline-based fluorescence probes for the biological chem-
istry of zinc. J. Am. Chem. Soc. 121, 11448–11458 (1999)
7. Walkup, G.K., Burdette, S.C., Lippard, S.J., Tsien, R.Y.: A new
(
300 MHz, DMSO-d ): d 5.50 (s, 4H), 7.37 (m, 4H), 7.74 (d,
6
1
H, J = 7.8 Hz), 7.82 (d, 2H, J = 6.9 Hz,), 8.23 (t, H,
2
1
3
J = 7.8 Hz), 8.35 (d, 2H, J = 7.8 Hz,), 13.10 (s, 2H).
C
NMR (75 MHz, DMSO-d ): d 170.0, 150.1, 149.2, 141.8,
6
1
1
39.4, 137.0, 125.9, 124.2, 123.3, 119.8, 111.5, 46.8. ESI
2?
cell-permeable fluorescent probe for Zn . J. Am. Chem. Soc.
22, 5644–5645 (2000)
?
MS: m/z [M ? H] = 428. Elemental analysis calcd. for
1
C H N O : C, 64.63; H, 4.01; N, 16.39. Found: C, 64.49;
23 17 5 4
18. Maruyama, S., Kikuchi, K., Hirano, T., Urano, Y., Nagano, T.: A
novel, cell-permeable, fluorescent probe for ratiometric imaging
of zinc ion. J. Am. Chem. Soc. 124, 10650–10651 (2002)
H, 4.11; N, 16.42.
1
9. Xue, L., Liu, C., Jiang, H.: A ratiometric fluorescent sensor with a
large Stokes shift for imaging zinc ions in living cells. Chem.
Commun. 9, 1061–1063 (2009)
Supporting information
1
1
13
IR, H-NMR of compound 5. IR, H & C-NMR, Mass of
20. Mikata, Y., Wakamatsu, M., Kawamura, A., Yamanaka, N.,
Yano, S., Odani, A., Morihiro, K., Tamotsu, S.: Methoxy-sub-
stituted TQEN family of fluorescent zinc sensors. Inorg. Chem.
2
Dibcid. Fluorescence titration of Cd , Job’s plot, plots of
?
2
?
2?
stability constants of Zn and Cd by UV–Vis and flu-
orescence and detection limit is available online.
4
5, 9262–9268 (2006)
21. Mashraqui, S.H., Khan, T., Sundaram, S., Betkar, R., Chandira-
mani, M.: A new intramolecular charge transfer receptor as a
2?
selective ratiometric ‘off–on’ sensor for Zn . Tetrahedron Lett.
8, 8487–8490 (2007)
4
2
2. Park, S.Y., Yoon, J.H., Hong, C.S., Souane, R., Kim, J.S., Mat-
thews, S.E., Vicens, J.: A pyrenyl-appended triazole-based
References
2
?
2?
calix[4]arene as a fluorescent sensor for Cd and Zn . J. Org.
1
. De Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T., Huxley,
A.J.M., McCoy, C.P., Rademacher, J.T., Rice, T.E.: Signaling
recognition events with fluorescent sensors and switches. Chem.
Rev. 97, 1515–1566 (1997)
Chem. 73, 8212–8218 (2008)
23. Fan, J., Peng, X., Wu, Y., Lu, E., Hou, J., Zhang, H., Zhang, R.,
2?
Fu, X.: A new PET fluorescent sensor for Zn . J. Lumin. 114,
125–130 (2005)
1
23