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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Electronic Supplementary Information Mesoporous polymeric microspheres with high affinity for phosphorylated biomolecules. Sudhirkumar Shinde* a, Jayashree Selvalatchmanan b, Anil Incel a, Maedeh Akhoundian a, Anne K Bendt b, Federico Torta c a Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE Malmö, Sweden b Singapore Lipidomics Incubator (SLING), Life Sciences Institute, National University of Singapore, 28 Medical Drive, Singapore c Singapore Lipidomics Incubator (SLING), Department of Biochemistry, YLL School of Medicine, National University of Singapore, 28 Medical Drive, Singapore * Corresponding authors: Sudhirkumar Shinde, Telephone: , sudhirkumar.shinde@mah.se 1
2 Figure S1. The SEM images of porous bulk monolith particles. The porous bulk monoliths (left side) was disintegrated into smaller particles (right side) after pressing with spatula or by normal hand press. Figure S2. Thermal gravimetric analysis traces (TGA) graph of porous silica, silica-polymer composite and porous polymer respectively. 2
3 Figure S3. ATR-FTIR spectra of porous silica, silica-polymer composite and porous polymer respectively. 3
4 Figure S4. ATR-FTIR overlay spectra of porous microscopic polymer and porous monolith (dotted line). 4
5 Figure S5. Representative collision-induced dissociation product ion mass spectra (in positive ionization mode) of TMS-derivatized synthetic stable isotope standard (d18:1 13C2D2-S1P, m/z 440, diamond symbol) yielded expected ions at m/z 60 (fragment A), m/z 113 (fragment B), and m/z 328 (fragment C). The former two fragments are expected to be invariant for LCB-P with different aliphatic compositions which is indeed the case as shown for corresponding product ion spectra of LCB-P d18:2 (b), S1P d18:1 (c), and S1P d18:0 (d), all derived from extracts of human blood plasma and results summarized in table (e). Figure S6. HPLC traces of chromatogram before and after rebinding of an equimolar mixture of Fmoc-pSer-OH, Fmoc-pTyr-OH in 95% MeCN + 0.1% TEA for porous polymer at 254 nm. 5
6 Figure S7. HPLC traces of chromatogram before and after rebinding of Fmoc-pSer-OH, Fmoc-pTyr-OH, Fmoc-sTyr-OH anf Fmoc-Tyr-OH in 95% MeCN + 0.1% TEA for porous polymer at 254 nm. 6
7 Table S1 Recovery studies of sphingosine-1-phosphate lipids Relative amounts 1 of S1P found in flow-through and wash fractions 13C 2 D 2 -S1P LCB-P (d16:1) SA1P S1P LCB-P LPC (d18:0) (d18:1) (d18:2) Wells Area Area Area Area Area Area Well Well Well Average StdDev %RSD Relative amounts of S1P in 3 elutions 13C 2 D 2 -S1P LCB-P (d16:1) SA1P S1P LCB-P LPC (d18:0) (d18:1) (d18:2) Wells Area Area Area Area Area Area Well Well Well Average StdDev %RSD Relative amounts of S1P in all fractions- Flow through + Wash + elutions Wells 13C2D2_S1P LCB-P (d16:1) SA1P S1P LCB-P LPC (d18:0) (d18:1) (d18:2) Well Well Well Average StdDev %RSD
8 Note: Well 1, Well 2 and Well 3 are three replicates. SPE experiment was carried out in three different wells of 96 well plate using same amount of the polymer. Table S2 Enrichment studies of LCB-Ps in plasma samples. Lipid extract of plasma sample ( derivatised with TMS), but NOT polymer Enriched 13C 2 D 2 -S1P S1P S1P S1P S1P LPC (d16:1) (d18:0) (d18:1) (d18:2) Name Area Area Area Area Area Area Plasma Plasma Plasma Average Std Dev %RSD Average of plasma (triplicate) Average: Total of 3 elutions (3 wells) Enrichment Factor 13C2D2_S1P S1P (d16:1) S1P (d18:0) S1P (d18:1) S1P (d18:2) LPC ,39 2,54 2,45 2,57 2,18 0,07 Note: Plasma 1, Plasma 2 and Plasma 3 are three replicates. 1 Relative amounts of S1P refers to the area under a chromatographic peak 8
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