;. Hz, , vol.4

J. C. Mhz-;-d, ? = 24.5 (C2), 25.2 (CH2), 25.5 (CH2), 27. 1(CH2), 27.7 (C3), vol.36, p.2

J. C. , CAr), Hz, C8), 78.9 (C4), 82.4 (d, JC,F = 168.0 Hz, C9), 124.0 (CHtriazole), 127.1 (CAr), vol.78

, Prepared from 26 according to procedure described for the synthesis of compound 33. Yield: 65% as a white foam

M. W. ,

D. ,

H. Nmr, D2O, 400 MHz): ? = 1.51-1.80 (m, 6H, H3a, H2a and 2 CH2), 1.86-1.98 (m, 1H, H2b)

J. Hz, 1. =-;-d, and J. =. , 2H, CH2), 3.16-3.26 (m, 2H, H5 and ½CH2), 3.42-3.52 (m, 3H, H4, H6 and H7), 3.61-3.77 (m, 4H, H8, CH and CH2), vol.3

, CH2), 43.7 (CH2), 50.7 (C1), vol.37

J. C. , F. =-;-d, J. C. , F. =-;-d, and J. C. , Hz, C8), 72.8 (C6), 75.6 (C4), Hz, C7), vol.54

. Esi-hrms, Synthesis of fluorinated and fluorescent C-glycosides and conjugation with RGD derivatives, vol.888

M. W. ,

H. Nmr, CD3)2SO, 250 MHz): ? = 1.52 (s, 6H, 2 CH3), 2.75 (s, 3H, CH3), 3.96 (s, 3H, CH3), 7.60-7.63 (m, 2H, HAr), 7.80-7.84 (m, 1H, HAr)

, -Phenylamino-1E,3E-butadien-1-yl)-1,3,3-trimethylindolium chloride 36

, HCl (0.85 mL) and malondialdehyde bis(dimethylacetal) (1.05 mL, 6.1 mmol) was added dropwise a solution of distilled water (21 mL), HCl (1.5 mL), and aniline (2.2 mL, 24.4 mmol). The reaction was stirred at 50°C during 5 hours. The precipitate was isolated by filtration to give 36

M. W. ,

H. Nmr, CD3)2SO, 250 MHz): ? = 6.25 (t, 1H, J3,2 = J3,4 = 12.5 Hz, H3), 7.27-7.33 (m, 2H, HAr), 7.37-7.40 (m, 4H, HAr), 7.45-7.51 (m, 4H, HAr)

, Yield: 10% as a colorless oil

M. W. ,

=. Rf, , vol.54

, D = -16.3 (c 0.06; MeOH)

H. Nmr, CD3OD, 400 MHz): ? = 1.49-1.60 (m, 1H, H3a), 1.65-1.74 (m, 1H, H3b), 1.76-1.86 (m, 1H, H2a), 1.90-1.99 (m, 1H, H2b)

;. Hz, , vol.3

, Hz, HAr), 7.30 (bt, 6H, J = 7.5 Hz, HAr), 7.49 (bd, 6H, J = 7.5 Hz, HAr). 13 C NMR, p.3

. Mhz, ? = 21.0 (CH3), 26.0 (C2), vol.29

. Cqar, ESI-HRMS [M+Na] + m/z = 554.2201 (calculated for C30H33N3NaO6: 554.2267). IR (cm -1 ): ? = 3364, 172.3 (C=O), pp.3-9, 1028.

, Yield: 15% as a colorless oil

M. W. ,

=. Rf, , vol.48

H. Nmr, CD3OD, 400 MHz): ? = 1.54-1.65 (m, 1H, H3a), 1.77-1.87 (m, 1H, H2a), 1.92-2.00 (m, 1H, H3b), 2.01-2.09 (m, 1H, H2b), 2.98 (dd, 1H, J9a,9b = 10.5 Hz, J9a,8 = 5.0 Hz, H9a), 3.18 (dd, 1H, J9b,8 = 2.0 Hz, H9b), 3.21-3.26 (m, 2H, H4 and H5), 3.37-3.51 (m, 3H, H1, H6 and H8, vol.9

, (CqAr), 145.6 (CqAr), 145.6 (CqAr) 172.3 (C=O). ESI-HRMS, 75.8 (C5), 77.7 (C6), 78.7 (C8), vol.80

, = 11.5 Hz, CH2Ph), 5.04 (d, 1H, J = 11.5 Hz, CH2Ph), 5.58 (s, 1H, H10), 7.35-7.40 (m, 8H, HAr), 7.49-7.52 (m, 2H, HAr). 13 C NMR (CDCl3, 100.6 MHz): ? = 25.0 (C2), vol.29, pp.51-57

, ESI-HRMS [M+H] + m/z = 426, 69.1 (C9), 70.6 (C8), 73.7 (C5), 74.7 (CH2Ph), 79.6 (C4), vol.82, 1016.

M. W. ,

=. Rf, , vol.53

D. , , vol.7

H. Nmr, CDCl3, 400 MHz): ? = 1.45-1.54 (m, 1H, H3a), 1.58-1.70 (m, 1H, H2b, vol.2, p.8

, and H4), 3.46 (app t, 1H, J7,6 = J7,8 = 9.0 Hz, H7), 3.67 (app t, 1H, J9a,9b = J9a,8 =10.0 Hz, H9a), 3.93

. Hz, CAr), CH2Ph), 5.52 (s, 1H, H10), 7.29-7.41 (m, 8H, HAr), 7.47-7.52 (m, 2H, HAr). 13 C NMR (CDCl3, 100.6 MHz): ? = 25.1 (C2), 29.2 (C3), 51.6 (C1), 69.0 (C9), 70.0 (C8), 75.2 (CH2Ph), 76.0 (C6), 79.1 (C4), 81.5 (C7 or C5), 81.8 (C7 or C5), 102.0 (C10), 126.4 (2 CAr), vol.128, 1026.

M. W. ,

=. Rf, , vol.69

D. ,

H. Nmr, CDCl3, 400 MHz): ? = 1.44-1.52 (m, 1H, H3a), 1.58-1.69 (m, 1H, H2b), 1.70-1.80 (m, 1H, H2b), 1.87-1.95 (m, 1H, H3b), vol.3

. Hz, , vol.51

, 69.1 (C9), 70.4 (C8), 75.2 (CH2Ph), 75.6 (CH2Ph), 79.5 (C4), 81.5 (C5), vol.82

, CAr), CAr), 129.1 (CAr), 137.6 (CqAr), vol.127, 1026.

M. W. ,

=. Rf, , vol.50

D. , , vol.6

. Mp, , pp.50-52

H. Nmr, CDCl3, 400 MHz): ? = 1.49-1.58 (m, 1H, H3a), 1.64-1.74 (m, 1H, H2b), 1.76-1.90 (m, 1H, H2b), 1.94-2.02 (m, 1H, H3b), 3.25 (td, 2H, J1,2 = 7.0 Hz, J1,3a = 1.5 Hz, H1), 3.33-3.38 (m, 2H, H4 and H5), 3.43 (ddd, 1H, J8,9b = 5.0 Hz, J8,7 = 9.0 Hz, J8,9a = 10.0 Hz, H8), 3.52 (app t, 1H, J6,7 = J6,5 = 9.0 Hz, H6), 3.59 (app t, 1H, J7,8 = J7,6 = 9.0 Hz, H7), 3.70 (app t, 1H, J9a,9b = J9a,8 =10.0 Hz, H9a), 4.20 (app ddt, 1H, J11a,11b = 12.5 Hz, J11a,12 = 6.5 Hz, J11a,13a = J11a,13b = 1.5 Hz, H11a), 4.31 (dd, 1H, J9b,8 = 5.0 Hz, H9b), 4.50 (app ddt, 1H, J11b,12 = 5.5 Hz, J11b,13a = J11b,13b = 1.5 Hz, H11b), 5.20 (b dddd, J13a,13b = 2.5 Hz, J13a,12 = 10.5 Hz, H13a), 5.29 (b dddd, vol.82, 1018.

M. W. ,

=. Rf, , vol.66

D. ,

H. Nmr, Hz, H5), 3.30 (t, 2H, J1,2 = 7.0 Hz, H1), 3.30-3.39 (m, 2H, H4 and H8), app t, 1H, J6,7 = J6,5 = 9.0 Hz, H6), 3.62 (app t, 1H, J7,6 = J7,8 = 9.0 Hz, H7), 3.66 (app t, 1H, J9a,9b = 10.0 Hz, H9a), 4.15 (app ddt, 1H, J11a,11b = 12.5 Hz, J11a,12 = 6.0 Hz, J11a,13a = J11a,13b = 1.5 Hz, H11a), vol.2, p.12

, and J13'b,12' = 17.5 Hz, H13b and H13'b), 5.53 (s, 1H H10), 5.83-6.00 (m, 2H, H12 and H12'), 7.34-7.40 (m, 3H, HAr), 7.46-7.50 (m, 2H, HAr). 13 C NMR (CDCl3, 100.6 MHz): ?, vol.82

, C10), 116.9 (C13), 117.4 (C13', vol.101

, ESI-HRMS [M+H] + m/z = 416.2170 (calculated for C22H30N3O5: 416.2180). IR (cm -1 ): ? = 3075, 129.0 (CAr), vol.134, pp.3-6, 1028.

M. W. ,

=. Rf, , vol.41

D. , , vol.5

H. Nmr, CD3)2CO, 400 MHz): ? 1.43 (s, 9H, CH3), 1.52-1.65 (m, 1H, H3a), 1.66-1.94 (m, 1H, H2a, H2b and H3b), vol.2

, Hz, H11a), 4.56 (d, 1H, H11b), 5.67 (s, 1H, H10), 7.35-7.41 (m, 3H, HAr), 7.44-7.52 (m, 2H, HAr). 13 C NMR ((CD3)2CO, 400 MHz): ? 25.2 (C2), 28.6 (C3 and 3 CH3), vol.51

, 69.1 (C9), 71.6 (C8), 75.8 (C5), 77.7 (C4), 79.4 (C7), vol.79

, ESI-HRMS, CAr), 129.7 (CAr), 138.7 (CqAr), 166.4 (C=O), vol.127

, IR (cm -1 ): ? = 3410, + m/z = 472.2047 (calculated for C22H31NaN3O7: 472.2060), 1013.

M. W. ,

=. Rf, , vol.35

D. , , vol.7

H. Nmr, CDCl3, 400 MHz): ? = 1.44-1.51 (m, 1H, H3a), 1.59-1.68 (m, 1H, H2a), 1.73-1.90 (m, 2H, H3b and H2b), 1.94-2.03 (m, 2H, H12), 2.78 (bt, 1H, J5.4 = J5,6 = 9.5 Hz, H5), vol.3

, Hz, H9a), 3.72 (ddd, 1H, J11a,11b = 12.0 Hz, J11a,12a = 9.5 Hz, J11a,12b= 5.5 Hz, H11a)

, = 4.5 Hz, H9b), 5.53 (s, 1H, H10), 7.28-7.33 (m, 3H, HAr), 7.41-7.45 (m, 2H, HAr), 7.64-7.69 (m, 2H, HAr), 7.76-7.80 (m, 2H, HAr). 13 C NMR (CDCl3, 100.6 MHz): ? 25.3 (C2), vol.29, 1013.

, were added dropwise, under argon at room temperature, BH3.THF (1M) (95 ?L, 0.93 mmol, 1 equiv.) and TMSOTf (5 ?L, 0.028 mmol, 0.3 equiv.). The solution was stirred for 20 minutes at room temperature, then 0.1 mL of Et3N was added followed by careful addition of MeOH (1 mL). The solution was concentrated and the crude product was co-evaporated with MeOH, dry CH2Cl2 (1 mL), p.90

M. W. ,

=. Rf, , vol.51

D. ,

H. Nmr, CDCl3, 400 MHz): ? = 1.42-1.52 (m, 1H, H3a), 1.60-1.70 (m, 1H, H2a), 1.76-1.91 (m, 2H, H3b and H2b), 2.01 (app qt, 2H, J12,11 = J12,13 = 7.0 Hz, H12)

, CAr), 138.2 (CqAr), 168.5 (2 C=O). ESI-HRMS [M+Na] + m/z = 561.2341 (calculated for C28H34N4NaO7: 561.2320). IR (cm -1 ): ? = 3364, 51.6 (C1), 61.1 (CH3), 62.4 (C9), 71.1 (C11), 75.0 (CH2Ph), vol.35, 1069.

, Yield: 40% as a colorless oil

M. W. ,

=. Rf, , vol.22

. D-=-+2,

H. Nmr, CDCl3, 400 MHz): ? = 1.41-1.50 (m, 1H, H3a), 1.60-1.70 (m, 1H, H2a), 1.76-1.90 (m, 2H, H2b and H3b), 1.90-2.06 (m, 2H, H11), vol.2, p.76

. Hz, 2H, H9a and H12b), 3.87-3.93 (m, 2H, H9b and H10a), 4.04 (ddd, 1H, J10b,10a = 13.5 Hz, J10b,11a = 9.0 Hz, J10b,11b = 4.5 Hz, H10b), 7.71-7.74 (m, 2H, HAr), 7.83-7.86 (m, 2H, HAr). 13 C NMR (CDCl3, 100.6 MHz): ? = 25.3 (C2), vol.28

, CAr), 51.6 (C1), 60.9 (CH3), 63.4 (C9), 69.5 (C12), 71.2 (C7), 78.8 (C4), vol.78

, 3) Preparation of non-radioactive references 4, vol.8, 1040.

, Diethyl-Amino-Sulfur Trifluoride) (34 µL, 0.26 mmol, 1.4 equiv) under argon at 0°C. The mixture was stirred 30 min at 0°C and 1h at rt, the mixture was then diluted with CH2Cl2 and hydrolyzed with water. The organic layer was washed with an aqueous saturated solution of NaHCO3 and with brine, then dried with MgSO4 and evaporated under vacuum. The crude product was purified by flash chromatography on silica gel, CH2Cl2 (3 mL) was added DAST

M. W. ,

=. Rf, , vol.41

H. Nmr, CDCl3, 400 MHz): ? = 1.43-1.54 (m, 1H, H3a), 1.60-1.71 (m, 1H, H2a), 1.78-1.91 (m, 2H, H3b and H2b), 2.02 (app qt, 2H, J11,10 = J11,12 = 7.0 Hz, H11)

. Mhz, ? = 25.3 (C2), vol.28

J. C. C8, 75.1 (CH2Ph), 77.3 (C7, JC,F = 6 Hz), vol.77

, 3 (C5), = 173.0 Hz), vol.84

M. W. ,

H. Nmr, CD3)2SO, 400 MHz) : ? = 0.89 (t, 3H, J24,23 = 7.5 Hz, H24), 1.50-1.62 (m, vol.4, p.18

=. J17, 16 = 7.0 Hz, H17), vol.2

, Hz, H22), 3.65 (s, 3H, N-CH3), 4.05-4.15 (m, 2H, H16), 6.40 (d, 1H, J = 13.5 Hz, H10 or H6), 6.51 (d, 1H, J = 13.5 Hz, H10 or H6), 6.74 (app bt, NH), 6.88 (app bt, 1H, J8,9 = J8,7 = 13.0 Hz, H8), 7.05-7.13 (m, 2H, HAr), 7.17-7.25 (m, 2H, HAr), 7.30-7.40 (m, 4H, HAr), 7.92 (app t, 1H, H7 or H9), 7.94 (app t, 1H, H9 or H7). 13 C NMR, vol.22

, 3 (CAr), 110.8 (CAr), 122.1 (CAr), 122.2 (CAr), 125.0 (CAr), C10 or C6), vol.110

, (C2), 173.4 (C21). ESI-HRMS [M] + m/z = 524.3708 (calculated for C35H46N3O + : 524.3635). IR (cm -1 ): ? = 2923, vol.128, 1006.

. 3h-indolium, 3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-3,3-dimethyl-1-[6-oxo-6-(benzylamino)hexyl]-inner salt, vol.3, p.71

, 18 mmol) in CH2Cl2 (5 mL) was added diisopropylcarbodiimide (DIC, 41 ?L, 0.26 mmol, 1.5 eq) and was stirred for 5 min. A solution of benzylamine (38 ?L, 0.36 mmol, 2 eq) in chloroform (1.5 mL) was then added. The solution was stirred for 16 hours, vol.100, p.38

M. W. ,

H. Nmr, CDCl3, 400 MHz): ? = 1.55 (bqt, 2H, J18,17 = J18,19 = 7.0 Hz, H18), 1.70 (s, vol.6

, CH3), 1.70 (s, 6H, 2 CH3), 1.78 (bqt, 2H, J19,18 = J19,20 = 7.0 Hz, H19), 1.85 (bqt, 2H, J17,18 = J17,16 = 7.0 Hz, H17), 2.40 (t, 2H, H20), vol.7, pp.31-38

, 3 (CAr), 36.1 (C20), 42.9 (C22), 44.5 (C16), 49.0 (C3), 49.4 (C15), 62.1 (C23), vol.103

, 3439 (calculated for C34H44N3O2 + : 526.3428). IR (cm -1 ): ? = 3316, vol.526, 1005.

. 3h-indolium, 3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl, vol.3, pp.3-4

, To a solution of compound 38 (150 mg, 0.27 mmol) in anhydrous CH2Cl2 (50 mL), were added under argon, DCC (62 mg, 0.3 mmol, 1.1 eq) and NHS (33 mg, p.0

M. W. ,

H. Nmr, CD3)2SO, 400 MHz): ? = 1.45-1.63 (m, 2H, H18), 1.61-1.84 (m, 16H, 4 CH3, p.19

, 82 (s, 4H, H23 and H24), 3.61 (s, 3H, 2.68 (t, 2H, J20,19 = 7.0 Hz, H20), vol.2

. Hz, H6 or H10), 6.58 (app t, 1H, J8,9 = J8,7 = 12.5 Hz, H8), 7.21-7.27 (m, 2H, HAr), 7.35-7.42 (m, 4H, HAr), 7.61 (d, 2H, J = 7.5 Hz, HAr), 8.34 (app t, 2H, H7 and H9). 13 C NMR, p.2

. Mhz, ? = 24.9 (C19), 25.1 (C18), 25.4 (C23 and C24), 26.4 (C17), 27.0 (2 CH3), vol.27

, 30.0 (C20), 31.1 (N-CH3), 43.2 (C3), 47.5 (C13), 48.8 (C16), 103.0 (C6 or C10), vol.103

, C6 or C10), 111.0 (CAr), 111.0 (CAr), vol.122

, 141.0 (CqAr), 141.1 (CqAr), 142.0 (CqAr), 142.7 (CqAr), 154.0 (C9 and C7), 168.8 (C21), 170.0 (C22 or C25), vol.128, 1015.

. 3h-indolium, 3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl, vol.3, pp.3-4

, 15 mmol) in anhydrous DMF (2 mL), was added under argon, ethanolamine (10 µL, 0.17 mmol, 1.1 eq). The solution was stirred 13h at room temperature. The solvent was evaporated under vacuum. The crude product was purified by flash chromatography on silica gel, vol.73

M. W. ,

H. Nmr, CDCl3, 400 MHz): ? = 1.55 (bqt, 2H, J18,17 = J18,19 = 7.0 Hz, H18), 1.69 (s, vol.6

, CH3), 1.69 (s, 6H, 2 CH3), 1.81 (bqt, 2H, J19,18 = J19,20 = 7.0 Hz, H19), 1.81-1.91 (m, 2H, H17), 2.41 (t, 2H, H20), 3.38-3.44 (m, 2H, H22), 3.60 (s, 3H, N-CH3), 3.72-3.77 (m, 2H, H23), 4.11 (bt, 2H, J16,17 = 6.5 Hz, H16), 6.36 (d, 1H, J = 13.5 Hz, H10 or H6), 6.58 (d, 1H, J = 13.5 Hz, H10 or H6), 7.00 (app bt, 1H, J8,9 = J8,7 = 12.5 Hz, H8), 7.07 (d, 1H, J = 7.5 Hz, HAr), 7.13 (d, 1H, J = 7.5 Hz, HAr), 7.18-7.26 (m, 2H, HAr), 7.30-7.42 (m, 4H, HAr), 7.81 (app t, 1H, H7 ou H9), 7.84 (app t, 1H, H7 or H9). 13 C NMR, vol.49

, 3 (CAr), 125.0 (CAr), 125.6 (CAr), 127.0 (C8), C6 or C10), 105.1 (C6 or C10), 110.3 (CAr), 111.2 (CAr), vol.122, p.1057, 1138.

, 12 mmol) solubilized in CH2Cl2 (4 mL) was added diisopropylcarbodiimide (DIC, 28 ?L, 0.18 mmol, 1.5 eq). The solution was stirred for 5 min at rt, then a solution of 69, p.38

M. W. ,

H. Nmr, CDCl3, 400 MHz): ? = 1.46-1.57 (m, 3H, H16 and H3a), 1.60-1.72 (m, 1H, H2a), 1.69 (s, 6H, 2 CH3), 1.70 (s, 6H, 2 CH3), 1.70-1.74 (m, 3H, H15 and H3b), 1.77-1.89 (m, 5H, H17, H11 and H2b), 2.37 (t, 2H, J20,19 = 7.0 Hz, H14), 2.84 (app t, 1H, J5,6 = J5,4 = 9.0 Hz, H5), vol.3

J. C. C7, F. C9, and J. C. , Hz), 78.0 (C8, JC,F = 18 Hz), 79.0 (C4), C22 or C33), 49.4 (C22 or C33), 51.6 (C1), 61.1 (CH3), 71.6 (C10), 75.1 (CH2Ph), vol.49

, ESI-HRMS [M+Na] + m/z = 875.5241 (calculated for C52H68FN6O5: 875.5230). IR (cm -1 ): ? = 2998, C27 or C25), 153.5 (C27 or C25), 173.0 (C23 or C29), vol.173, 1039.

, To a solution of peptide c(RGDfK) (1 equiv, 165 µmol, 100 mg) and NEt3 (2.5 equiv, p.497

, mL) was added 1-(pent-4-ynoyloxy)pyrrolidine-2,5-dione (1.2 equiv, 199 mmol, 38.8 mg). The reaction was stirred for 16 hr at rt. The solution was evaporated under vacuum and the crude product was solubilized in water. The solution was freeze-dried to give 76

M. W. ,

. Esi-hrms, , vol.684

, Compound 77

, To a solution of 75 (5 mg, 4.9 µmol) and N-pentynoique derivative c(RGDfK) 76 (5 mg, vol.6

, 17 mL), were added at room temperature an aqueous solution of sodium ascorbate (20µL, 1.2 µmol, 0.2 equiv) and an aqueous solution of Cu(OAc)2 resin was filtered off and the resulting solution was freeze-dried. Purification was achieved on Sephadex LH20. Elution with MeOH provided pure fluoro C-glycopeptide 77

M. W. ,

. Esi-hrms, , vol.2

, Prepared from 66 following the procedure to synthetize 69. Yield: 70% as a white gum

M. W. , 444.96 g/mol

. Esi-hrms,

, The solution was stirred at 0°C for 1h. A freshly prepared solution of, vol.78

M. W. ,

H. Nmr, CDCl3, 400 MHz): ?= 1.42-1.59 (m, 3H, H16 and H3a), 1.60-1.69 (m, 1H, H2a), vol.1, p.2

, and H3b), 1.90 (app qt, 2H, J11,12 = J11,10 = 6.5 Hz, H11), vol.2, p.203

. Hz, H24 or H28), 6.54 (bd, 1H, J = 13.5 Hz, H24 or H28), 6.84 (app bt, 1H, J26,25 = J26, p.27

, = 12.5 Hz, H26), 7.06 (d, 1H, J = 7.5 Hz, HAr), 7.10 (d, 1H, J = 7.5 Hz, HAr), 7.18-7.25 (m, 3H, HAr), 7.29-7.41 (m, 8H, HAr), 7.89 (app t, 1H, H27 or H25), 7.91 (app t, 1H, H27 or H25). 13 C NMR (CDCl3, 100.6 MHz): ?= 25.3 (C2 and C15)

, 30.5 (C11), 31.6 (N-CH3), vol.36

, C22 or C33), 51.6 (C1), 61.1 (CH3), 62.3 (C9), 71.7 (C10), vol.74

, 3 (CqAr), 142.1 (CqAr), 143.0 (CqAr), C27 or C25), 172.7 (C23 or C29), 173.1 (C23 or C29), 173.6 (C13). HRMS [M] + m/z = 873.5302 (calculated for C52H69N6O6: 873.5273), vol.128, 1028.

, min, Alltima C8, 5µm, 150x4.6 mm, 55/45 ACN/H2O in isocratic condition, vol.1

. F-fluoride, P6, vacuum -200 mbar) and passed through a Sep-Pak ® light QMA-carbonate cartridge (P5-P4), where [ 18 F]fluoride was trapped and [ 18 O]water was collected for recycling (P1). The QMA-carbonate cartridge was then flushed with nitrogen gas flow during 40 seconds (pressure 400 mbar; vacuum -300 mbar). The trapped 18 F-fluoride was eluted from the QMA-carbonate cartridge into reaction vessel, ~ 5 GBq) in [ 18 O]water was recovered in the AIO synthesiser via the plunger, vol.2

, After cooling at 30°C, the reaction mixture was recovered into syringe 4 (SA4, P12) containing 1.5 mL of WFI (Bag W), the reactor was pressurized (pressure 500 mbar) acetonitrile (Vial A, P2) taken with syringe 3 (SA3, P9), The triflated precursor 21 (Vial C, P8) was pressurized (pressure 500 mbar) and was added into the reaction vessel (reactor 1, P7, vacuum -800 mbar) containing the dried K[ 18 F]F-K222 complex, pp.32-34

, Preparation of 18 F-fluoro-C-glycoside based prosthetic group

, HPLC solvent (~3 mL, reactor 2) was evaporated by heating at 80°C (vacuum -300 to -1000 mbar) 15 min, and then under nitrogen gas flow during 1 minute

, After complete evaporation and cooling at 30°C, saponification of the

. F-glycoside, was performed for 9 min at 30°C with an aqueous NaOH 1M solution (vial E, P31) added (vacuum -500 mbar) after pressurization of the vial

, Aqueous HCl 1M solution (vial F, P33) was then added (pressure 500 mbar, vacuum -500 mbar) by the same way to neutralize the solution containing

, ~850 MBq) were added (vacuum -500 mbar) after pressurization of each vial (pressure 500 mbar), sodium ascorbate (vial G, P30), propargylated peptide 30 (vial H, P29) and Cu(OAc)2 (vial I, P28). The solution was heated at 55°C during 25 min under nitrogen gaz flow (pressure 150 to 250 mbar; vacuum -500 to -800 mbar). The elution lines and SA4 were washed with WFI (10 mL, Bag W). The reaction mixture was then diluted with 3 mL of WFI

, Crude product in SA4 was transferred into the injection loop of the semipreparative HPLC and was purified with the 2 nd HPLC column (Vydac 218TP C18, solvent: ACN/H2O the dilution vial containing 10 mL of WFI (vial J, P35), secondes (pressure 500 mbar, vacuum -300 mbar) the solution was passed through a cartridge pre-charged with Chelex ® 100 resin (V15-V16) to remove copper, and was recovered in syringe 4 (P12)

K. , The Oasis HLB cartridge was rinsed with 1,8 mL of NaCl 0.9% (Bag N, taken with SA4) pushed into final product vial (P26), and then flushed by nitrogen gas flow during 10 seconds

, An aliquot of final product

T. 1%-of, Standard curve relating mass to UV absorbance was performed on analytical HPLC to check molar activity

, Platelet-rich plasma (PRP) was prepared by centrifugation of whole blood at 190g for 10 min at 20°C. The remaining blood was again centrifuged at 1750g for 10 min at 20°C to obtain platelet-poor plasma (PPP). PRP was adjusted to 300?10 9 platelets/L by addition of autologous PPP. Platelet reactivity was measured by light transmission aggregometry, Monovette ® tubes containing 0.106 M Trisodium citrate solution (Sarstedt)

, Clonetics® human aortic smooth muscle cells (VSMCs) grown to subconfluence in

. Stawowy, Clonetics® SmGM®-2 Smooth Muscle Growth Medium-2 (Lonza Sales) were used at passage 3-6. Adhesion of VSMCs to vitronectin was measured as previously described

, 2004) using commercially available human vitronectin coated 96-well microplates (R&D Systems). Briefly, VSMCs were adjusted to 6.10 5 cells/mL in DMEM/F12 and incubated for 5

, min at room temperature with C-glyco"RGD" or reference RGDC or c(RGDfC) peptides at

, VI-Molecular modeling Standard amino acids, ions and the sugar moiety were described by means of the CHARMMM36 [270,271] force field whereas triazole and linker were described with the CHARMM General Force Field (CGENFF)

, 273] In order to use standard force-field parameters, the fluorine atom beard by the sugar moiety was systematically replaced by a hydroxyl group. The latter substitution in similar compounds was shown to preserve the global behaviour of RGD-based peptides towards integrins

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