Photochromic azo polysemicarbazides with biocompatibility behavior

Abstract

Two kinds of azo polysemicarbazides were prepared based on 3, 3′-azobis (benzoylhydrazide) (ABH) and two kinds of diisocyanates via solution polymerization. The structures were characterized by Fourier-transform infrared (FT-IR) technique and elemental analysis. Inherent viscosities of the polymers were 0.32 and 0.29 dL/g and both could be dissolved in H₂SO₄ and polar organic solvents. Thermal gravimetric analysis (TGA) presented a multi-step degradation and a decomposition temperature range of 230–280 °C. And photoisomerization of the azo polymers in solvent of N, N-dimethyl acetamide (DMAc) was confirmed by Ultraviolet-visible spectroscopy (UV-Vis), suggested the isomerization appearing under the ultraviolet irradiation at 365 nm and recovering completely by visible light irradiation or kept in the dark. Transmission electron microscopy (TEM) of polysemicarbazides before and after soaking in bovine serum albumin (BSA) solution confirmed the biocompatibility of azo polymers.

Keywords

azo polysemicarbazides / isomerization / photochromism / biocompatibility

References

[1] Churikov V. M., Hung M. F. Real-time Monitoring of All-optical Poling of Azo-dye Polymer Thin Film[J]. Opt. Lett., 2000, 25: 960-962.

[2] Aoshima Y., Egami C., Kawata Y., . Two-way Opticalmemory for Azobenzene-containing Urethane-urea Copolymer Films[J]. Opt. Commun., 1999, 165: 177-182.

[3] Tirelli N., Solaro R. A., Ciardelli F., . Structure-activity Relationship of New NLO Organic Materials Based on Push-pull Azo Dyes: Side Chain Polymers[J]. Polymer, 2000, 41: 415-421.

[4] Andruzzi L., Altomare A., Ciardelli F., . Holographic Gratings in Azobenzene Side Chain Polymethacrylates[J]. Macromolecules, 1999, 32: 448-454.

[5] Angiolini L., Caretti D., Giorgini L., . Optically Active Methacrylic Polymers Bearing Side-chain Conjugated Azoaromatic Chromophores[J]. Synth. Met., 2000, 115: 235-239.

[6] Fiorini C., Charra F., Nunzi J. M., . Photoinducednon Centrosymmetry in Azo-dye Polymers[J]. Nonlinear. Opt., 1995, 9: 339-347.

[7] Lee T. S., Kim D. Y., Jiang X. L., . Photoinduced Surface Relief Gratings in High-Tg Main-chain Azoaromatic Polymer Films[J]. J. Polym. Sci., Part A: Polym. Chem., 1998, 36: 283-289.

[8] Tracey M., David E. G. Characterization of Azo Coupling Adducts of Benzenediazonium Ions with Aromatic Amino Acids in Peptides and Proteins[J]. Chem. Res. Toxicol., 1997, 10(12): 1378-1386.

[9] Taiji I., Fumihiko H., Takashi M., . Molecula-Shape Imprinting and Immobilization of Biomolecules on a Polymer Containing Azo Dye[J]. Langmuir, 2006, 22: 2747-2753.

[10] Parra S., Nadtotechenko V., Albers P., . Discoloration of Azo-Dyes at Biocompatible pH-Values through an Fe-Histidine Complex Immobilized on Nafion via Fenton-like Processes[J]. J. Phys. Chem. B, 2004, 108: 4439-4448.

[11] Vollmer M. S., Clark T. D., Steinem C. M., . Photoswitchable Hydrogen-Bonding in Self-Organized Cylindrical Peptide Systems[J]. Angewandte Chemie International Edition, 1999, 38(6): 1598-1601.

[12] Ven D., Mooter G., Maris B., . Use of Azo Polymers for Colon-specific Drug Delivery[J]. J. Phar. Sci., 1997, 6(12): 1321-1327.

[13] Vale R. O., Milligan R. A. The Way Things Move: Looking Under The Hood of Molecular Motor Proteins[J]. Science, 2002, 288: 88-95.

[14] Hugel T., Holland N. B., Cattani A., . Single-molecule Optomechanical Cycle[J]. Science, 2002, 296: 1103-1106.

[15] Holland N. B., Hugel T., Neuert G., . Single Molecule Force Spectroscopy of Azobenzene Polymers: Switching Elasticity of Single Photochromic Macromolecules[J]. Macromolecules, 2003, 36(6): 2015-2023.

[16] Frazer A. H., Wallenberger F. T. Aliphatic Polyhydrazides: A New Low Temperature Solution Polymerization[J]. Polym. Sci. Part A. Polym. Chem., 1964, 2: 1137-1146.

[17] Frazer A. H., Wallenberger F. T. Aromatic Polyhydrazides: A New Class of Highly Bonded, Stiff Polymers[J]. J. Polym. Sci. Part A., Polym. Chem., 1964, 2: 1147-1156.

[18] Frazer A. H., Sweeny W., Wallenberger F. T. Poly(1, 3, 4-oxadiazole) Fibers: New Fibers With Superior High Temperature Resistance[J]. J. Polym. Sci. Part A., Polym. Chem., 1964, 2: 1157-1165.

[19] Campbell T. W., Foldi V. S., Farago J. Condensation Polymers From Diisocyanates with Dihydrazides and Hydrazine[J]. J. Appl. Polym. Sci., 1959, 2: 155-162.

[20] Cao L. H., Zhou C. J., Liu Y. T., . The Synthesis of N-(Glycosylthioureylene)-aminothiophosphonic and -diaminoth-ophos-phinic O-aryl Esters[J]. Chem. Soc., 2001, 48(2): 207-210.

[21] Abdellatif G., Imam H. A Study of The Laser Plasma Parameters at Different Laser Wavelengths[J]. Spectrchimica. Acta. Part B, 2002, 57: 1155-1165.

[22] Ruijtzer K., John A. W., Lefebe D. J., . Approaches to the Synthesis of Ureapeptoid Peptidomimetics[J]. Tetrahedron. lett., 1997, 38: 5335-5338.

[23] Wang X. C., Li Z., Da Y. X., . A Facile Method to 1,4-diacylsemicarbazides: Synthesis of 1-aryloxyacetyl-4-(4-chlorobenzoyl)-thiosemicarbazides and Semicarbazides[J]. Synth. Commun., 2000, 30(18): 3405-3411.

[24] Molina P., Tarraga A., Lopez J. L., . Preparation and Heterocyclization Reactions of Ferrocenylazido Ketones. Useful Building Blocks for the Synthesis of Ferrocenyl-substituted Azaheterocycles[J]. Organomet. Chem., 1999, 584: 147-158.

[25] Chohan Z. H., Pervez H., Kausar S., . Synthesis and Characterization of Antibacterial Co(II), Cu(II), Ni(II), and Zn(II) Complexes of Acylhydrazine Derived Pyrrolyl Compounds[J]. Synth. React. Inorg. Met.Org. Chem., 2002, 32: 529-543.

[26] Vogel A. I. Text Book of Practical Organic Chemistry[M], 1996 5th ed. Essex Addison Wesley Longman Ltd

[27] Aruna P., Venkateshwarlu U., Ganga R. Thermal and Mechanical Properties of Fiber-forming Poly(urethane semicarbazide) s[J]. J. Appl. Polym. Sci., 2002, 83: 86-93.