# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008
Supporting Information
Mono- and Dicationic short PEG and Methylene Dioxyalkylglycerols for use in Synthetic Gene Delivery Systems
Christopher A. Hurley,a, John B. Wong,a Jimmy Ho,a Michele Writer,b Scott A. Irvine,b M. Jayne Lawrence,c Stephen L. Hartb, Alethea B. Tabora and Helen C. Hailesa,*
a
Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK. . Fax: +44 20 7679 7463; Tel: +44 20 7679 4654; E-mail: h.c.hailes@ucl.ac.uk
b
Molecular Immunology Unit, Institute of Child Health, University College London, 30 Guilford Street, London WC1N 1EH, UK
c
Pharmaceutical Science Research Division, King's College London, Stamford Street, London, SE1 9NH, UK
Contents General Experimental Methods 9-Tetradecyn-1-ol 9-Tetradecyn-1-yloxy mesylate (Z)-9-Tetradecen-1-ol (Z)-9-Tetradecen-1-yloxy mesylate 2,3-Di-((9Z)-tetradecenyloxy)propyl-N,N-dimethylamine (9) 5-Bromo-3-oxopentan-1-ol (11) 8-Bromo-3,6-dioxooctan-1-ol (12) 11-Bromo-3,6,9-trioxoundecan-1-ol (13) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-[2-(2-hydroxyethoxy)ethyl]-N,N-dimethylammonium bromide (15) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}-N,Ndimethylammonium bromide (16) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-{2-[2-(2-{2-[2-(2hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl}-N,N-dimethylammonium bromide (18) S7 2,3-Di-((11Z)-hexadecenyloxy)propyl-N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-N,Ndimethylammonium bromide (19) 2,3-Di-((11Z)-hexadecenyloxy)propyl-N-{2-[2-(2-{2-[2-(2S1 S7 S7 S6 S3 S3 S4 S4 S4 S5 S5 S6 S6
hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl}-N,N-dimethylammonium bromide (20) S8 2,3-Di-(tetradec-9-ynyloxy)propyl-N-(2-[2-hydroxyethoxy]ethyl)N,N-dimethylammonium bromide (21) bromide (22) bromide (23) dimethylammonium bromide (24) 1,8-Dibromo-3,6-dioxooctan-1-ol (26) 1,11-Dibromo-3,6,9-trioxoundecan-1-ol (27) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-{2-[2-(2-bromoethoxy)ethoxy]ethyl}-N,Ndimethylammonium bromide (32) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-(2-{2-[2-(2-bromoethoxy)ethoxy]ethoxy}ethyl)-N,Ndimethylammonium bromide (33) S11 2,3-Di-((9Z)-octadecenyloxy)propyl-N-(3-bromohexyl)-N,N-dimethylammonium bromide (35) S11 2,3-Di-((9Z)-octadecenyloxy)propyl-N-(3-bromodecyl)-N,N-dimethylammonium bromide (36) S12 2,3-Di-((9Z)-octadecenyloxy)propyl-N-{2-[2-(2-(N,N,N-trimethylammonium)ethoxy)ethoxy]ethyl}N,N-dimethylammonium dibromide (38) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-(2-{2-[2-(2-(N,N,Ntrimethylammonium)ethoxy)ethoxy]ethoxy}ethyl)-N,N-dimethylammonium dibromide (39) S12 2,3-Di-((9Z)-octadecenyloxy)propyl-N-3-(N,N,N-trimethylammoniumhexyl)-N,Ndimethylammonium dibromide (41) 2,3-Di-((9Z)-octadecenyloxy)propyl-N-3-(N,N,N-trimethylammoniumdecyl)-N,Ndimethylammonium dibromide (42) Lipid formulation Sizing protocol Transfection protocol Table 1: Transfection Data for Compounds 37–42 Table 2: Transfection Data for Compounds 15, 16, 17a (+ DOPE), Lipofectin Table 3: Transfection Data for Compounds DOTMA, 17a and Lipofectin Table 4: Transfection Data for Compound 23 (+ DOPE), Lipofectin Table 5: Relative Transfection Data for Compounds 21-24 (+ DOPE) References S2 S13 S13 S14 S14 S15 S15 S16 S16 S16 S13 S12 S10 S8 S9 S9 S9 S10 S10 2,3-Di-((9Z)-tetradecenyloxy)propyl-N-(2-[2-hydroxyethoxy]ethyl)-N,N-dimethylammonium 2,3-Di-((11Z)-tetradecenyloxy)propyl-N-(2-[2-hydroxyethoxy]ethyl)-N,N-dimethylammonium 2,3-Di-((11Z)-tetradecenyloxy)propyl-N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-N,N-

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