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,
,
,
Cq-Ar), MHz, CDCl3) ????138.9, 138.6, 138.2, 137.7, 137, vol.6 ,
, CH-Ph), vol.95
, C-3'); 38.0 (C-1''); 37.4 (C-2); 31.06 (C-12'') 30.4 (C-2''), vol.38
CDCl3) ???173.0 (C-1'); 172.5 (C-5'), MHz, vol.151, issue.125 ,
, , pp.132-138
, Diisopropylethylamine salt of DBCO-?-sulfo-?-alanine derivative (37)
A solution of activated DBCO 36 (20 mg, 0.05 mmol, 1.0 eq.), ?-sulfo-?-alanine (8 mg ,
1:1, 0.05 M) was stirred at room temperature under an argon atmosphere overnight. The reaction mixture was concentrated under vacuum then purified by C-18 cartridge, mixture of THF/DMF (1.0 mL ,
, 0 °C was added O-(N-succinimidyl, p.15
, 31 mg, 0.19 mmol, 1.0 eq.) in DMF (1.0 mL, 0.19 M) and DIPEA (100 µL, 0.58 mmol, 3.0 eq.) was then added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. Then, the crude product was purified by C-18 cartridge
, 99 g/mol Chemical formula: C23H22N2O7S ? (C6H15N)2
,
DMSO-d6) ???11.97?(s, 1H, COOH); 8.30 (br s, 500 MHz ,
, , vol.1, pp.50-57
,
, H-6b); 5.04 (d, J = 14.0 Hz, 1H, H-6a); 3.50-3.30 (m, 3H, 2 H-3'', H-2''); 3.14 (m, Hz, vol.1
, , vol.148
, CH-Ar); 129.0 (CH-Ar), vol.132
, C-3"'), vol.53
, , vol.12
, C-6), vol.55, pp.37-43
, Triethylamine salt of DBCO-PEG4-?-sulfo-?-alanine-?-alanine-DNP derivative (15)
, CH2Cl2/H2O/TFA (7.7 mL, 10:1:2.5, 0.01 M) was added the DBCO-PEG4-N
, The reaction mixture was concentrated under vacuum, then the residue was diluted with CH3OH and co-evaporated with toluene. The crude material was purified by flash chromatography over silica gel (CH2Cl2/CH3OH, 100:0 to 80:20) to give an orange oil. Then, a solution of DBCO-PEG4-NH2 (30 mg, 0.07 mmol, 0.5 eq.) in mixture of THF/DMF (2.0 mL, 1:1, 0.035 M) at 0 °C was added (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, (77 mg, 0.15 mmol, 1.0 eq.) and N,N-diisopropylethylamine, (300 µL, 1.7 mmol, 12.0 eq.). The reaction mixture was stirred at room temperature under an argon atmosphere for 3 hours then cooled to 0°C. A solution of DBCO-PEG4-NH2 derivative in THF/DMF (0.5 mL, 1:1, 0.14 M) and DIPEA (100 µL, 0.54 mmol, 7.7 eq.) was then added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum, then the residue was dissolved in 10.0 mL of TEAB buffer (50 mM) and lyophilized, The reaction mixture was stirred at room temperature for 3 hours, vol.60, p.40
, 16 g/mol Chemical formula: C42H51N7O14S ? C6H15N
, HRMS
,
Biological part : Biological part for eukaryotic cells, Materials ,
, All chemical and biological reagents were of analytical or cell culture grade, obtained from commercial sources, and used without further purification
, American Type Culture Collection. RPMI 1640 medium (ref. 61870-044), colorless RPMI 1640 medium (ref. 11835-030), solutions of trypsin-EDTA (ref. 25300054), phosphate-buffered saline solution (PBS), conjugate streptavidin Alexa Fluor® 488 (ref. S-32354), pp.conjugate dinitrophenyl-KLH
, Penicillin-streptomycin (10 000 u/ 10 000 µg/mL) solution (ref. 17-602E) was purchased from Lonza. Bovine Serum Albumin (ref. 04-100-810c) was obtained from Euromedex. DMSO (ref. D8418) were purchased from Sigma-Aldrich. All the others organic molecules were synthesized in the group, some as described previously. Solutions stocks of organic and, Antibody Alexa Fluor® 488 (ref. A-11097) were obtained from Thermo Fisher Scientific. Conjugate streptavidin FluoProbes 565A (ref. FP-CA5610) was purchased from Interchim. Azide-PEG3-5/6-CarboxyRhodamine 110 (N3-CR110, ref. CLK-AZ105) was purchased from Jena Bioscience. Fetal Bovine Serum (FBS, ref. S1810-100) was purchased from Biowest
, Ac4GalNAc and Ac4GlcNAc: 30 mM in DMSO, Ac4GalNCyp 5, Ac4GalNCCyp, vol.3
, , vol.9, p.20
, DNP, vol.15, p.10
, , vol.12, p.50
, Streptavidin-AF488: 2 mg/mL in PBS
, Streptavidin-FP565: 1 mg/mL in PBS
, Antibody anti-DNP-AF488: 2 mg/mL in PBS. N3-CR110: 1 mM in DMSO. Sodium ascorbate: 50 mM in PBS
, Tris(3-hydroxypropyltriazolylmethyl)amine (THPTA): 10 mM in PBS. Copper sulfate: 2 mM in H2O
, Aminoguanidine hydrochloride: 40 mM in PBS. Cells were counted using a Vi-CELL® XR Cell Viability Analyzer (Beckman Coulter) and Vi
Beckman Coulter) and were grown in a Binder® C150 incubator of CO2. The viability of PC-3 cells was controlled on an Olympus CKX41 Culture Microscope equiped with a camera Axio Cam ERC5S (Zeiss). The cells were ,
, Heraeus® Megafuge® 40R (ThermoFisher Sicentific) or in a microstar 12 (VWR)
, Around 3 000 cells per sample were analyzed by flow cytometry (CytoFLEX XS, Beckman-Coulter), Data were analyzed using CytExpert 2.0 software
, Unless otherwise specified, PC-3 cells were grown in RPMI 1640 medium supplemented with 10% (v/v) FBS, 500 u/mL penicillin and 500 ?g/mL streptomycin (complete RPMI 1640 medium). In all cases, cells were incubated at 37 °C in a humidified environment under 5% CO2. After defrosting, cells were cultivated in a 75 mL flask (700 000 cells) in complete RPMI 1640 (12 mL). The flask was, Microscopy. Cells were cultivated in a ?-dish (35 mm high) glass botton (Ibidi®, ref. 81158) analyzed by an inverted confocal Leica SP8-X (DMI 6000)
, Then, the medium was removed, cells were washed with PBS (4 mL) and were trypsinized (4 mL, p.5
, Cells were transferred to 15 mL tube and centrifuged at 2 500 rpm for 3 min at 20 °C. The supernatant was removed and the cell pellets were resuspended in 2 mL of complete RPMI 1640. Cells were counted, then cultivated in a new 75 mL flask (700 000 cells) in complete RPMI 1640 (12 mL). The operation is renewed twice a week. After 1 month, new cells were defrosting. Synthetized mono saccharides
, Tz-PEG4-Biot 12 are solubilized in PBS/DMSO, vol.9
, Fluorescent probes. Streptavidin-AF488, Streptavidin-FP565 and Antibody anti-DNP, vol.98
, Sodium ascorbate, copper sulfate pentahydrate, aminoguanidine, THPTA and N3-CR110 are solubilized in PBS/DMSO, 97.5:2.5 (v/v) Protocol for mono incorporation of mono saccharide and mono labeling by SPAAC or IED-DA. step: cells were treated with a functionalized carbohydrate in complete RPMI
mL) or with culture medium (3 mL) for 24 hours. Then the medium was removed, cells were washed three times with PBS (3 x 500 ?L). Labeling step: cells were treated with a labeling tool in PBS/DMSO, vol.99, p.400 ,
, ?L) or with PBS (400 ?L) at 26 °C under agitation (60 rpm) for 60 min. Cells were washed with PBS
, Cells were transferred to 1.5 mL microtubes and centrifuged at 2 000 rpm for 4 min at room temperature. The supernatant was removed and the cell pellets were washed with complete RPMI 1640 (500 ?L) and twice with PBS (2 x 500 ?L). The cells were resuspended in 500 ?L of PBS. Finally, the cells were analyzed by Flow Cytometry. Protocol for dual incorporation of mono saccharides and mono labeling by SPAAC or IED-DA, PBS containing 1% (w/v) BSA (400 µL) or with PBS containing 1% (w/v)
mL) or with culture medium (3 mL) for 24 hours. Then the medium was removed, cells were washed three times with PBS (3 x 500 ?L). Labeling step: cells were treated with a labeling tool in PBS/DMSO, vol.99, p.400 ,
, ?L) or with PBS (400 ?L) at 26 °C under agitation (60 rpm) for 60 min. Cells were washed with PBS
, Recognition step: cells were treated with a fluorescent probe in PBS containing 1% (w/v)
, BSA (400 µL) or with PBS containing 1% (w/v) BSA (400 µL) at 26 °C under agitation (60 rpm) for
, x 500 ?L) and were trypsinized (500 ?L, 6 min at 37 °C), then neutralized with complete medium RPMI 1640 (500 supernatant was removed and the cell pellets were washed with complete RPMI 1640 (500 ?L) and twice with PBS (2 x 500 ?L), Then the medium was removed, cells were washed three times with PBS
, Finally, the cells were submitted to Flow Cytometry. Biological part for prokaryotic cells, Materials
, All chemical and biological reagents were of analytical or cell culture grade, obtained from commercial sources, and used without further purification. Corynebacterium glutamicum strains was purchased from the American Type Culture Collection
D8418) was purchased from Sigma-Aldrich. Phosphatebuffered saline solution (PBS), Gene Frame seals (ref. 11560294), Microscope Slides (ref ,
, Microscope Coverslips (ref. 11961988) were purchased from Thermo Fisher Scientific. 5/6-Carboxyrhodamine 110-PEG4-Alkyne (CCH-CR110, ref. CLK-TA-106) was purchased from Jena Bioscience. All the others organic molecules were synthesized in the group, some as described previously. Solutions stocks of organic and inorganic compounds were prepared as followed: Sodium ascorbate, p.50
3-triazol-4-yl)methyl)amine (TGTA): 40 mM in PBS buffer, Copper sulfate, vol.2, issue.1, pp.20-22 ,
, CCH-CR110: 2 mM in DMSO
, Around 20 000 cells per sample were analyzed by flow cytometry (CytoFLEX XS, Beckman-Coulter), Data were analyzed using CytExpert 2.0 software
Samples of 2 µL were deposited on agar (1%) pads placed on glass slides and then covered by coverslips. Fluorescence microscopy experiments were performed on a confocal straight Leica SP8 (DM 6000), using a 63x PLAN APO oil immersion lens (Leica), an argon laser (488 nm) and a GaAsP Hybrid detector (Hamamatsu). The microscope was operated with LAS-X ,
, Synthetized saccharides. 2N3-Tre 40 and 2epiN3-Tre 41 are solubilized in water
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,
, Uridine Diphosphate 6-deoxy-2,4-diN-Acétylglucosamine Uridine Diphosphate 2,4-diN-AcétylBacilosamine 6-deoxy-ManNAc4NAc 6-deoxy-2,4-diN
,
, Acide Cytosine Monophosphate, vol.5
, Uridine Diphosphate 4-oxo-6-deoxy-N-AcétylAltrosamine UDP-6-deoxy-L-IdoNAc4N
, Uridine Diphosphate 6-deoxy-2,4-diN-Acétyl-L-Idosamine UDP-6-deoxy-L-GulNAc4NAc
, Uridine Diphosphate 6-deoxy-2,4-diN-Acétyl-L-Gulosamine
, Acide Cytosine Monophosphate, vol.5
, Uridine Diphosphate 6-deoxy-2,4-diN-Acétyl-L-Altrosamine
, Acide Cytosine Monophosphate, vol.5