Synthesis of Two Compounds with Self-Assembled Monolayer Properties: Riboflavin 2', 3', 4' , 5' Tetra Octadecanoate & Bis (Phosphatidyl Ethanol) Protoporphyrin IX Amide

Document Type : Research Note


1 Biotechnology Research & Development Center, Darou Pakhsh Pharmaceutical Mfg.Co, Tehran, I.R. IRAN

2 Department of Cellular and Molecular Biology, Faculty of Science , Azarbaijan University of Tarbiat Moalem, Tabriz, I.R. IRAN

3 Department of Chemistry, Faculty of Basic Sciences, Tarbiat Modares University, Tehran, I.R. IRAN

4 Institute of Biochemistry and Biophysics (IBB), University of Tehran, Tehran, I.R. IRAN

5 Department of Biophysics, Faculty of Biological Sciences, Tarbiat Modares University, Tehran, I.R. IRAN



Riboflavin and protoporphyrin IX are two molecules that participate in oxidation and reduction reactions in the living cell. Changing some functional groups of riboflavin and protoporphyrin IX can provide compounds with self-assembled monolayer properties with wide applications in designing the molecular electronic devices. In this study, the amphiphilic structure of riboflavin and protoporphyrin IX is resulted from the reaction of stearic acid with riboflavin and phosphatidyl ethanol amine with protoporphyrin IX. The reaction products were purified and analyzed by different spectroscopy techniques such as IR, Uv-Vis, fluorimetry and NMR. The electron transfer ability was confirmed by cyclic voltammetry. The finding approves that the produced amphiphilic compounds have kept theirs intrinsic properties as well. 


Main Subjects

[1] Allen j.B., “Integrated Chemical Systems”, john Wiley & sons, U.S.A, p p. 7, 301(1994).
[2] Metals P., Nanotechnology Overview, Advanced Materials and Processes, 157, p. 48, (2000).
[3] Gregory T., “Nanotechnology”,Springer-verlag,New York, U.S.A, Chap 1, p.8, (1998).
[4] James K.G., Nanoscale Science of Single Molecules Using Local Probes, Science, 283, p.1683, (1999).
[5] David S.G., Biomolecules and Nanotechnology, American Scientist, 88, p. 230 (2000).
[6] Nikolai V., “Biomolecular Electronics”, Birkhauser,Boston, p.218 (1998).
[7] Rudolph A.S., Biomaterial Biotechnology Using Self-Assembled Lipid Micro Structures, J Cell Biochem, 56, p. 183 (1994).
[8] Ziegler C., Gopel W., Biosensor Development, Curr Opin Chem Biol., 2, p. 585 (1998).
[9] Tien H.T, Salamon Z., Ottova A., Lipid Bilayer Based Sensors and Biomolecular Electronics, Crit Rev Biomed Eng., 18, p. 223 (1991).
[10] Wolf gang G., Bioelectronics and Nanotechnologies, Biosensors and Bioelectronics, 13, p. 723 (1998).
[11] Albert B. “Molecular Biology of the Cell”, Gerland Pub.,New York, U.S.A, pp. 653-684 (1994).
[12] Sadeghi S.J. et al. Engineering Non-Physiological Electron Transfer, Biochemical Society Transactions, 27, P. A58 (1999).
[13] Lelivel S.R. et al., Engineering Redox Proteins by Modular Building Blocks, "4thESF-ABIWorkshop on Biomolecular Interaction, Recognition and Dynamics", (1997).
[14] Carlos A.C. et al, Docking Simulations and Electron Transfer Studies Between Redox Proteins: Flavodoxin and Cytochrome C533, "Euco-CC2 2nd European Conference on Computational Chemistry", P-80 (1997).