1 Supporting information for: Ferrocene-modified Phospholipid: An Innovative Precursor for Redox- Triggered Drug Delivery Vesicles Selective to Cancer Cells Tomer Noyhouzer, † Chloé L'Homme, ‡ Isabelle Beaulieu, † Stephanie Mazurkiewicz, † Sabine Kuss, † Heinz-Bernhard Kraatz, § Sylvain Canesi,* ‡ Janine Mauzeroll* † † Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A OB8 ‡ Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre- Ville, Montréal, H3C 3P8, Québec, Canada § Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, Ontario M1C 1A4, Can- ada TABLE OF CONTENTS Instrumentation………………………………………………………………………………….. 3 Figures Figure 1 1 H NMR spectra of Phospholipid 3 ……………………………………………………. 4 Figure 2 31 P NMR spectra of Phospholipid 3 …………………………………………………….. 5 Figure 3 13 C NMR spectra of Phospholipid 3………………………………………………………6 Figure 4 GUVs preparation: The different vial compositions during the process………..……… 6 Figure 5 Diagram describing the preparation of doxorubicin loaded GUVs for the live cell experiments ………………………………………………………………………………………. 7 Figure 6 The indirect immunofluorescence imaging complete process diagram………………..... 8 Figure 7: Synthesis of Phospholipid 3 and the self-assembly of the redox active unilamellar vesicles…………………………………………………………………………………..… 9 Figure 8 Cyclic voltammetry if ferroceneacetic acid……………………………………………… 9 Figure 9 Cyclic voltammetry of TBA-PF6 in both aerobic and anaerobic conditions…………….. 10 Figure 10 Cyclic voltammetry of Phospholipid 3……………………………………………….… 10 Figure 11 Optical micrograph of redox active GUVs and fluorescent micrographs of calcein AM loaded GUVs…………………………………………………………………………….… 11 Figure 12 Fluorescent micrographs of GUVs preloaded with calcein AM before and after 5 min Illumination………………………………………………………………………...……… 11 Figure 13 SECM approach curves over redox active GUVs……………………………………… 12 Figure 14 TEM and EDX measurements of the redox active GUVs……………………………… 12