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Supporting Information for:
Thiophene-based fluorescent probes with low cytotoxicity and high photostability for lysosomes in living cells
Agostina Lina Capodilupo,1,a Viviana Vergaro,1,a Francesca Baldassarre,b Antonio Cardone,c
Giuseppina Anna Corrente,d Claudia Carlucci,a Stefano Leporatti,a Paride Papadia,e Giuseppe
Gigliafg and Giuseppe Ciccarella.ah *
a Istituto Nanoscienze – CNR, National Nanotechnology Laboratory (NNL), Via Arnesano, 73100
Lecce, Italy. E-mail: [email protected]
b Università del Salento, via Piazza Tancredi, 7, 73100 Lecce. Italy
c Istituto di Chimica dei Composti Organo Metallici (ICCOM) – Consiglio Nazionale delle Ricerche
CNR, Via Orabona, 4 – 70125 Bari, Italy.
d Università della Calabria, via Pietro Bucci, 87036 Arcavacata di Renze, Cosenza, Italy
f Center for Biomolecular Nanotechnologies (CBN) Fondazione Istituto Italiano di Tecnologia (IIT),
Via Barsanti 1, Arnesano, 73010, Italy
g Dipartimento di Matematica e Fisica “Ennio De Giorgi”, Università del Salento, Via Monteroni,
73100, Lecce, Italy.
h Dipartimento di Ingegneria dell'Innovazione, Università del Salento, Via Monteroni, 73100, Lecce,
Italy.
S1
Contents of Supporting Information
S3 Fig. S3. UV-vis absorption.
S4 Fig. S4 pH sensitivity of TC1 and TC2.
S5 Fig. S5 Qualitative analysis of LTR photobleaching obtained by confocal microscopy
S6 Fig. S6 Qualitative analysis of MTR photobleaching obtained by confocal microscopy
S7 Fig. S7 Qualitative analysis of TC1 photobleaching obtained by confocal microscopy
S8 Fig. S8 Qualitative analysis of TC2 photobleaching obtained by confocal microscopy
S9 1H-NMR, 13C-NMR, spectra of compounds.
S2
Fig.S3 Normalized absorbance (a) and emission (b) spectra in DMSO of TC1 and TC2.
Fig.S3 Normalized absorbance (c) and emission (d) spectra in H2O of TC1 and TC2.
Table 1 Summary of spectroscopic data of TC dyes.dye solvent λabs (nm) Δλ(nm) λem (nm) ε (104 M-1cm-1) ΦPL
TC1 CH2Cl2 442 86 528 1.86 0.051DMSO 444 87 531 2.14 0.079H2Oa 452 150 602 1.60 <0.001
TC2 CH2Cl2 496 40 536 4.27 0.007DMSOH2Oa
498492
31152
529644
3.192.13
0.009<0.001
Standard: [Ru(bpy)3]2+ (Φ =0.028) in H2O. a The measurements were carried out dissolving in DMSO / H2O (1:125 v/v).
S3
pH sensitivity of TC1 and TC2.
Fig.S4 The Absorbance (a) and the fluorescence intensities (b) in H2O of TC1 and TC2 as a function of pH.
S4
Fig S5 Micrographs obtained by confocal microscopy of MCF 7 cells stained with LTR (0.075 μM). To check the photostability of commercial LTR the fluorescence intensity in the consecutive t-scan mode was determined for 30 min (time interval of data determination was indicated above each micrographs). Excitation wavelength was 514 nm. Scale bar, 5 m
S5
Fig. S6 Micrographs obtained by confocal microscopy of MCF 7 cells stained with MTR (0.1 μM). To check the photostability of commercial MTR the fluorescence intensity in the consecutive t-scan mode was determined for 30 min (time interval of data determination was indicated above each micrographs). Excitation wavelength was 514 nm. Scale bar, 5 m
S6
Fig S7 Micrographs obtained by confocal microscopy of MCF 7 cells stained with TC1 (2.0 μM). To check the photostability of commercial TC1 the fluorescence intensity in the consecutive t-scan mode was determined for 30 min (time interval of data determination was indicated above each micrographs). Excitation wavelength was 488 nm. Scale bar, 5 m
S7
Fig. S8 Micrographs obtained by confocal microscopy of MCF 7 cells stained with TC2 (2.0 μM). To check the photostability of commercial TC2 the fluorescence intensity in the consecutive t-scan mode was determined for 30 min (time interval of data determination was indicated above each micrographs). Excitation wavelength was 488 nm
S8
Compound 3
ppm (f1)0.000.501.001.502.002.503.003.504.004.505.005.506.006.507.007.508.008.50
7.601
7.591
7.155
7.145
1.00
1.02
ppm (f1)6.907.007.107.207.307.407.507.607.707.80
1.00
1.02
ppm (f1)0255075100125150175200
175.9
87
143.3
74
133.0
3213
1.024
122.5
97
S9
Compound TC1
ppm (f1)0.000.501.001.502.002.503.003.504.004.505.005.506.006.507.007.508.008.50
7.584
7.573
7.360
7.339
7.321
7.278
7.253
7.186
7.166
7.150
6.439
6.428
1.00
1.944.154.60
1.03
ppm (f1)6.256.506.757.007.257.507.75
1.00
1.94
4.15
4.60
1.03
ppm (f1)255075100125150175
176.6
24
160.5
95
146.4
74
132.7
6013
1.155
129.8
0512
9.558
129.4
3412
5.017
124.6
5811
4.158
S10
Compound TC2
ppm (f1)0.501.001.502.002.503.003.504.004.505.005.506.006.507.007.508.00
7.338
7.248
7.181
6.428
4.179
1.566
1.233
2.00
1.73
3.146.307.49
3.92
ppm (f1)0255075100125150175200
164.4
5716
0.380
152.9
6114
6.154
136.7
6313
5.093
129.4
4612
4.656
120.0
8311
4.591
88.88
7
60.95
3
13.99
8
S11