Creation of unique supramolecular nanoarchitectures utilizing natural polysaccharide as a one-dimensional host

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 68, Issue 1, 2010, Pages 25-47

  Numata, Munenori ^a  

^a KYOTO PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Helical polymer; Inclusion complex; Nanomaterials; Polysaccharide; Self assemble

Indexed keywords

EID: 84255191191     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9754-z     Document Type: Review

References (117)

1. Rao, V. S. R., Qasba, P. K., Balaji, P. V., Chandrasekaran, R.: Conformation of Carbohydrates. Harwood Academic Publishers, The Netherlands (1998).
2. Frampton, M. J., Anderson, H. L.: Insulated molecular wires. Angew. Chem. Int. Ed. 46, 1028-1064 (2007).
3. Immel, S., Lichtenthaler, F. W.: Starch/Stärke 52 (2000).
4. Kim, O.-K., Choi, L.-S.: Supramolecular inclusion complexation of amylose with photoreactive dyes. Langmuir 10, 2842-2846 (1994).
5. Choi, L.-S., Kim, O.-K.: Unusual thermochromic behavior of photoreactive dyes confined in helical amylose as inclusion complex. Macromolecules 31, 9406-9408 (1998).
6. Sanji, T., Kato, N., Tanaka, M.: Induction of optical activity in oligosilanes by chiral wrapping with β-1, 3-glucan (schizophyllane). Chem. Lett. 34, 1144-1145 (2005).
7. Sanji, T., Kato, N., Kato, M., Tanaka, M.: Helical folding in a helical channel: chiroptical transcription of helical information through chiral wrapping. Angew. Chem. Int. Ed. 44, 7301-7304 (2005).
8. Kida, T., Minabe, T., Okabe, S., Akashi, M.: Partially-methylated amyloses as effective hosts for inclusion complex formation with polymeric guests. Chem. Commun. 1559-1561 (2007).
9. Kadokawa, J., Kaneko, Y., Yagaya, H., Chiba, K.: Synthesis of an amylose-polymer inclusion complex by enzymatic polymerization of glucose 1-phosphate catalyzed by phosphorylase enzyme in the presence of polyTHF: a new method for synthesis of polymer-polymer inclusion complexes. Chem. Commun. 449-450 (2001).
10. Rekharsky, M. V., Inoue, Y.: Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875-1917 (1998).
11. Li, G., McGown, L. B.: Molecular nanotube aggregates of β- and γ-cyclodextrins linked by diphenylhexatrienes. Science 264, 249-251 (1994).
12. Pistolis, G., Malliaris, A.: Nanotube formation between cyclodextrins and 1, 6-diphenyl-1, 3, 5-hexatriene. J. Phys. Chem. 100, 15562-15568 (1996).
13. Michels, J. J., O'Connell, M. J., Taylor, P. N., Wilson, J. S., Cacialli, F., Anderson, H. L.: Synthesis of conjugated polyrotaxanes. Chem. Eur. J. 9, 6167-6176 (2003).
14. Gattuso, G., Menzer, S., Nepogodiev, S. A., Stoddart, J. F., Williams, D. J.: Carbohydrate nanotubes. Angew. Chem. Int. Ed. 36, 1451-1454 (1997).
15. Harada, A.: Design and construction of supramolecular architectures consisting of cyclodextrins and polymers. Adv. Polym. Sci. 133, 141-191 (1997). Springer Berlin/Heidelberg.
16. Harada, A., Li, J., Kamachi, M.: Synthesis of a tubular polymer from threaded cyclodextrins. Nature 364, 516-518 (1993).
17. Harada, A.: Cyclodextrin-based molecular machines. Acc. Chem. Res. 34, 456-464 (2001).
18. Wenz, G., Han, B. H., Müller, A.: Cyclodextrin rotaxanes and polyrotaxanes. Chem. Rev. 106, 782-817 (2006).
19. Raymo, F. M., Stoddart, J. F.: Interlocked macromolecules. Chem. Rev. 99, 1643-1663 (1999).
20. Nepogodiev, S. A., Stoddart, J. F.: Cyclodextrin-based catenanes and rotaxanes. Chem. Rev. 98, 1959-1976 (1998).
21. Yanaki, T., Norisuye, T., Fujita, H.: Triple helix of schizophyllum commune polysaccharide in dilute solution. 3. Hydrodynamic properties in water. Macromolecules 13, 1462-1466 (1980).
22. Yanaki, T., Ito, W., Tabata, K., Kojima, T., Norisuye, T., Takano, N., Fujita, H.: Correlation between the antitumor activity or a polysaccharide schizophyllan and its triple-helical conformation in dilute aqueous solution. Biophys. Chem. 17, 337-342 (1983).
23. Bohn, J. A., BeMiller, J. N.: (1-3)-β-d-Glucans as biological response modifiers: a review of structure-functional activity relationships. Carbohydr. Polym. 28, 3-14 (1995).
24. Sato, T., Norisuye, T., Fujita, H.: Melting behavior of schizophyllum commune polysaccharides in mixture of water and dimethyl sulfoxide. Carbohydr. Res. 95, 195-204 (1981).
25. Stokke, B. T., Elgsaeter, A., Brant, D. A., Kitamura, S.: Supercoiling in circular triple-helical polysaccharides. Macromolecules 24, 6349-6351 (1991).
26. Sato, T., Norisuye, T., Fujita, H.: Triple helix of schizophyllum commune polysaccharide in dilute solution. 5. Light scattering and refractometry in mixtures of water and dimethyl sulfoxide. Macromolecules 16, 185-189 (1983).
27. Atkins, E. D. T., Parker, K. D.: Cyclic triad of hydrogen bonds in a helical polymer. Nature 220, 784-785 (1968).
28. Demleitner, S., Kraus, J., Franz, G.: Synthesis and antitumour activity of derivatives of curdlan and lichenan branched at C-6. Carbohydr. Res. 226, 239-246 (1992).
29. Gao, Y., Katsuraya, K., Kaneko, Y., Mimura, T., Nakashima, H., Uryu, T.: Synthesis, enzymatic hydrolysis, and anti-HIV activity of AZT-spacer-curdlan sulfates. Macromolecules 32, 8319-8324 (1999).
30. Katsuraya, K., Nakashima, H., Yamamoto, N., Uryu, T.: Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure. Carbohydr. Res. 315, 234-242 (1999).
31. Yoshida, T., Yasuda, Y., Mimura, T., Kaneko, Y., Nakashima, H., Yamamoto, N., Uryu, T.: Synthesis of curdlan sulfates having inhibitory effects in vitro against AIDS viruses HIV-1 and HIV-2. Carbohydr. Res. 276, 425-436 (1995).
32. Katsuraya, K., Ikushima, N., Takahashi, N., Shoji, T., Nakashima, H., Yamamoto, N., Yoshida, T., Uryu, T.: Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection. Carbohydr. Res. 260, 51-61 (1994).
33. Na, K., Park, K. H., Kim, S. W., Bae, Y. H.: Self-assembled hydrogel nanoparticles from curdlan derivatives: characterization, anti-cancer drug release and interaction with a hepatoma cell line (HepG2). J. Control. Release 69, 225-236 (2000).
34. Sakurai, K., Shinkai, S.: Molecular recognition of adenine, cytosine, and uracil in a single-stranded RNA by a natural polysaccharide: schizophyllan. J. Am. Chem. Soc. 122, 4520-4521 (2000).
35. Sakurai, K., Uezu, K., Numata, M., Hasegawa, T., Li, C., Kaneko, K., Shinkai, S.: β-1, 3-Glucan polysaccjarides as novel one-dimensional hosts for DNA/RNA, conjugated polymers and nanoparticles. Chem. Commun. 4383-4398 (2005).
36. Koumoto, K., Umeda, M., Numata, M., Matsumoto, T., Sakurai, K., Kunitake, T., Shinkai, S.: Low Mw sulfated curdlan with improved water solubility forms macromolecular complexes with polycytidylic acid. Carbohydr. Res. 339, 161-167 (2004).
37. Hasegawa, T., Umeda, M., Numata, M., Fujisawa, T., Haraguchi, S., Sakurai, K., Shinkai, S.: Click chemistry on curdlan: a regioselective and quantitative approach to develop artificial β-1, 3-glucans with various functional appendages. Chem. Lett. 35, 82-83 (2006).
38. Hasegawa, T., Umeda, M., Numata, M., Li, C., Bae, A.-H., Fujisawa, T., Haraguchi, S., Sakurai, K., Shinkai, S.: Click chemistry on polysaccharides: a convenient, general and monitorable approach to develop (1-3)-β-d glucans. Carbohydr. Res. 341, 35-40 (2006).
39. Numata, M., Matsumoto, T., Umeda, M., Koumoto, K., Sakurai, K., Shinkai, S.: Thermal stability of schizophyllan (SPG)/Poly(C) triple strands is controllable by α-amino acid modification. Bioorg. Chem. 31, 163-171 (2003).
40. Hasagawa, T., Umeda, M., Matsumoto, T., Numata, M., Mizu, M., Koumoto, K., Sakurai, K., Shinkai S.: Lactose-appended schizophyllan is a potential candidate as a heptocyte-targeted antisense carrier. Chem. Commun. 382-383 (2004).
41. Hasegawa, T., Fujisawa, T., Numata, M., Matsumoto, T., Umeda, M., Karinaga, R., Mizu, M., Koumoto, K., Kimura, T., Okumura, S., Sakurai, K., Shinkai, S.: Schizophyllans carrying oligosaccharide appendages as potential candidates for cell-targeted antisense carrier. Org. Biomol. Chem. 2, 3091-3098 (2004).
42. Hasegawa, T., Fujisawa, T., Numata, M., Umeda, M., Matsumoto, T., Kimura, T., Okumura, S., Sakurai, K., Shinkai, S.: Single-walled carbon nanotubes acquire a specific lectin-affinity through supramolecular wrapping with lactose-appended schizophyllan. Chem. Commun. 2150-2151 (2004).
43. Hasegawa, T., Fujisawa, T., Haraguchi, S., Numata, M., Karinaga, R., Kimura, T., Okumura, S., Sakurai, K., Shinkai, S.: Schizophyllan-folate conjugate as a new non-cytotoxic and cancer-targeted antisense carrier. Bioorg. Med. Chem. Lett. 15, 327-330 (2005).
44. Ikeda, M., Hasegawa, T., Numata, M., Sugikawa, K., Sakurai, K., Fujiki, M., Shinkai, S.: Instantaneous inclusion of a polynucleotide and hydrophobic guest molecules into a helical core of cationic β-1, 3-glucan polysaccharide. J. Am. Chem. Soc. 129, 3979-3988 (2007).
45. Ikeda, M., Minari, J., Shimada, N., Numata, M., Sakurai, K., Shinkai, S.: Complex formation between cationic β-1, 3-glucan and hetero-sequence oligodeoxynucleotide and its delivery into macrophage-like cells to induce cytokine secretion. Org. Biomol. Chem. 5, 2219-2224 (2007).
46. Ikeda, M., Haraguchi, S., Numata, M., Shinkai, S.: Controlled stability of the triple-stranded helical structure of a β-1, 3-glucan with a chromophoric aromatic moiety at a peripheral position. Chem. Asian. J. 2, 1290-1298 (2007).
47. Iijima, S.: Helical microtubules of graphitic carbon. Nature 354, 56-58 (1991).
48. Iijima, S., Ichihashi, T.: Single-shell carbon nanotubes of 1-nm diameter. Nature 363, 603-605 (1993).
49. Zheng, M., Jagota, A., Semke, E. D., Diner, B. A., Mclean, R. S., Lustig, S. R., Tassi, R. E. R.: DNA-assisted dispersion and separation of carbon nanotubes. Nat. Mater. 2, 338-342 (2003).
50. Zheng, M., Jagota, A., Strano, M. S., Santos, A. P., Barone, P., Chou, S. G., Diner, B. A., Dresselhaus, M. S., Mclean, R. S., Onoa, G. B., Samsonidze, G. G., Semke, E. D., Usrey, M., Walls, D. J.: Structure-based carbon nanotube sorting by sequence-dependent DNA assembly. Science 302, 1545-1548 (2003).
51. Nakashima, N., Okuzono, S., Murakami, H., Nakai, T., Yoshikawa, K.: DNA dissolves single-walled carbon nanotubes in water. Chem. Lett. 32, 456-457 (2003).
52. Takahashi, T., Tsunoda, K., Yajima, H., Ishii, T.: Isolation of single-wall carbon nanotube bundles through gelatin wrapping and unwrapping process. Chem. Lett. 31, 690-691 (2002).
53. Pantarotto, D., Partidos, C. D., Graff, R., Hoebeke, J., Briand, J. P., Prato, M., Bianco, A.: Synthesis, structural characterization, and immunological properties of carbon nanotubes functionalized with peptides. J. Am. Chem. Soc. 125, 6160-6164 (2003).
54. Dieckmann, G. R., Dalton, A. B., Johnson, P. A., Razal, J., Chen, J., Giordano, G. M., Munoz, E., Musselman, I. H., Baughaman, R. H., Draper, R. K.: Controlled assembly of carbon nanotubes by designed amphiphilic peptide helices. J. Am. Chem. Soc. 125, 1770-1777 (2003).
55. Zorbas, V., Ortiz-Acevedo, A., Dalton, A. B., Yoshida, M. M., Dieckmann, G. R., Draper, R. K., Baughman, R. H., Yacaman, M. J., Musselman, I. M.: Preparation and characterization of individual peptide-wrapped single-walled carbon nanotubes. J. Am. Chem. Soc. 126, 7222-7227 (2004).
56. Star, A., Steuerman, D. W., Heath, J. R., Stoddart, J. F.: Starched carbon nanotubes. Angew. Chem. Int. Ed. 41, 2508-2512 (2002).
57. Kim, O. K., Je, J., Baldwin, J. W., Kooi, S., Phehrsson, P. E., Buckley, L. J.: Solubilization of single-wall carbon nanotubes by supramolecular encapsulation of helical amylose. J. Am. Chem. Soc. 125, 4426-4427 (2003).
58. Sano, M., Kamino, A., Okamura, J., Shinkai, S.: Ring closure of carbon nanotubes. Science 293, 1299-1301 (2001).
59. Numata, M., Asai, M., Kaneko, K., Hasegawa, T., Fujita, N., Kitada, Y., Sakurai, K., Shinkai, S.: Curdlan and schizophyllan (β-1, 3-glucans) can entrap single-wall carbon nanotubes in their helical superstructure. Chem. Lett. 33, 232-233 (2004).
60. Kimura, T., Koumoto, K., Sakurai, K., Shinkai, S.: Polysaccharide-polynucleotide complexes (III): a novel interaction between the β-1, 3-glucan family and the single-stranded RNA Poly(C). Chem. Lett. 1242-1243 (2000).
61. Numata, M., Asai, M., Kaneko, K., Bae, A.-H., Hasegawa, T., Sakurai, K., Shinkai, S.: Inclusion of cut and as-grown single-walled carbon nanotubes in the helical superstructure of schizophyllan and curdlan (β-1, 3-glucans). J. Am. Chem. Soc. 127, 5875-5884 (2005).
62. Pouget, J. P., Laridjani, M., Jozefowicz, M. E., Epstein, A. J., Scherr, E. M., MacDiarmid, A. G.: Structural aspects of the polyaniline family of electronic polymers. Synth. Met. 51, 95-101 (1992).
63. Woo, H. S., Tanner, D. B., Huang, W. S., MacDiarmid, A. G.: Polaron lattice in highly conducting polyaniline: theoretical and optical studies. Phys. Rev. Lett. 59, 1464-1467 (1987).
64. Lu, F. L., Wudl, F., Nowak, M., Heeger, A. J.: Phenyl-capped octaaniline (COA): an excellent model for polyaniline. J. Am. Chem. Soc. 108, 8311-8313 (1986).
65. Numata, M., Hasegawa, T., Fujisawa, T., Sakurai, K., Shinkai, S.: β-1, 3-Glucan (schizophyllan) can act as a one-dimensional host for creation of novel poly(aniline) nanofiber structures. Org. Lett. 6, 4447-4450 (2004).
66. Buey, J., Swager, T. M.: Three-strand conducting ladder polymers: two-step electropolymerization of metallorotaxanes. Angew. Chem. Int. Ed. 39, 608-612 (2000).
67. Sauvage, J. P., Kern, J. M., Bidan, G., Divisia-Blohorn, B., Vidal, P. L.: Conjugated polyrotaxanes: improvement of the polymer properties by using sterically hindered coordinating units. New J. Chem. 26, 1287-1290 (2002).
68. Martin, R. E., Diederich, F.: Linear monodisperse p-conjugated oligomers: model compounds for polymers and more. Angew. Chem. Int. Ed. 38, 1350-1377 (1999).
69. Hecht, S., Frechet, J. M. J.: Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science. Angew. Chem. Int. Ed. 40, 74-91 (2001).
70. Sato, T., Jiang, D. L., Aida, T.: A blue-luminescent dendritic rod: poly(phenyleneethynylene) within a light-harvesting dendritic dnvelope. J. Am. Chem. Soc. 121, 10658-10659 (1999).
71. Langeveld-Voss, B. M. W., Janssen, R. A. J., Christiaans, M. P. T., Meskers, S. C. J., Dekkers, H. P. J. M., Meijer, E. M.: Circular dichroism and circular polarization of photoluminescence of highly ordered poly{3, 4-di[(S)-2-methylbutoxy]thiophene}. J. Am. Chem. Soc. 118, 4908-4909 (1996).
72. Goto, H., Okamoto, Y., Yashima, E.: Metal-induced supramolecular chirality in an optically active polythiophene aggregate. Chem. Eur. J. 8, 4027-4036 (2002).
73. Kim, J., McQuade, D. T., McHugh, S. K., Swager, T. M.: Ion-specific aggregation in conjugated polymers: highly sensitive and selective fluorescent ion chemosensors. Angew. Chem. Int. Ed. 39, 3868-3872 (2000).
74. Tan, C., Atas, E., Müller, J. G., Pinto, M. R., Kleiman, V. D., Schanze, K. S.: Amplified quenching of a conjugated polyelectrolyte by cyanine dyes. J. Am. Chem. Soc. 126, 13685-13694 (2004).
75. Zahn, S., Swager, T. M.: Three-dimensional electronic delocalization in chiral conjugated polymers. Angew. Chem. Int. Ed. 41, 4226-4230 (2002).
76. DiCesare, N., Pinto, M. R., Schanze, K. S., Lakowica, J. R.: Saccharide detection based on the amplified fluorescence quenching of a water-soluble poly(phenylene ethynylene) by a boronic acid functionalized benzyl viologen derivative. Langmuir 18, 7785-7787 (2002).
77. Kumaraswamy, S., Bergstedt, T., Shi, X., Rininsland, F., Kushon, S., Xia, W., Ley, K., Achyuthan, K., McBranch, D., Whitten, D.: Fluorescent-conjugated polymer superquenching facilitates highly sensitive detection of proteases. Proc. Natl. Acad. Sci. USA 101, 7511-7515 (2004).
78. Pinto, M. R., Schanze, K. S.: Physical sciences-chemistry. Proc. Natl. Acad. Sci. USA 101, 7505-7510 (2004).
79. Fan, C., Plaxco, K. W., Heeger, A. J.: High-efficiency fluorescence quenching of conjugated polymers by proteins. J. Am. Chem. Soc. 124, 5642-5643 (2002).
80. Wosnick, J. H., Mello, C. M., Swager, T. M.: Synthesis and application of poly(phenylene ethynylene)s for bioconjugation: a conjugated polymer-based fluorogenic probe for proteases. J. Am. Chem. Soc. 127, 3400-3405 (2005).
81. Morikawa, M., Yoshihara, M., Endo, T., Kimizuka, N.: ATP as building blocks for the self-Assembly of excitonic nanowires. J. Am. Chem. Soc. 127, 1358-1359 (2005).
82. Ichino, Y., Minami, N., Yatabe, T., Obata, K., Kira, M.: Molecular orientation in vacuum-deposited peralkyloligosilane thin films. J. Phys. Chem. B 105, 4111-4117 (2001).
83. Nakashima, H., Fujiki, M., Koe, J. R., Motonaga, M.: Solvent and temperature effects on the chiral aggregation of poly(alkylarylsilane)s bearing remote chiral groups. J. Am. Chem. Soc. 123, 1963-1969 (2001).
84. Peng, W., Motonaga, M., Koe, J. R.: Chirality control in optically active polysilane aggregates. J. Am. Chem. Soc. 126, 13822-13826 (2004).
85. Haraguch, S., Hasegawa, T., Numata, M., Fujiki, M., Uezu, K., Sakurai, K., Shinkai, S.: Oligosilane-nanofibers can be prepared through fabrication of permethyldecasilane within a helical superstructure of schizophyllan. Org. Lett. 7, 5605-5608 (2005).
86. Fujiki, M.: Ideal exciton spectra in single- and double-screw-sense helical polysilanes. J. Am. Chem. Soc. 116, 6017-6018 (1994).
87. Würthner, F., Yao, S., Beginn, U.: Highly ordered merocyanine dye assemblies by supramolecular polymerization and hierarchical self-organization. Angew. Chem. Int. Ed. 42, 3247-3250 (2003).
88. Parins, L. J., Thalacker, C., Würthner, F., Timmerman, P., Reinhoudt, D. N.: Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly. Proc. Nat. Acad. Sci. USA 98, 10042-10045 (2001).
89. Jones, R. M., Lu, L., Helgeson, R., Bergstedt, T. S., McBranch, D. W., Whitten, D. G.: Building highly sensitive dye assemblies for biosensing from molecular building blocks. Proc. Nat. Acad. Sci. USA 98, 14769-14772 (2001).
90. Yao, S., Beginn, U., Gress, T., Lysetska, M., Würthner, F.: Supramolecular polymerization and gel formation of bis (merocyanine) dyes driven by dipolar aggregation. J. Am. Chem. Soc. 126, 8336-8348 (2004).
91. Hannah, K. C., Armitage, B. A.: DNA-templated assembly of helical cyanine dye aggregates: a supramolecular chain polymerization. Acc. Chem. Res. 37, 845-853 (2004).
92. Heuer, W.-B., Kim, O.-K.: Influence of hemicyanine dye structures on spectral properties of their supramolecular complexes with amylose. Chem. Commun. 2649-2650 (1998).
93. Kim, O.-K., Je, J., Jernigan, G., Buckley, L., Whitte, D.: Super-helix formation induced by cyanine J-aggregates onto random-coil carboxymethyl amylose as template. J. Am. Chem. Soc. 128, 510-516 (2006).
94. Kashida, H., Asanuma, H., Komiyama, M.: Insertion of two pyrene moieties into oligodeoxyribonucleotides for the efficient detection of deletion polymorphisms. Chem. Commun. 2768-2769 (2006).
95. Kashida, H., Asanuma, H., Komiyama, M.: Alternating hetero H aggregation of different dyes by interstrand stacking from two DNA-dye conjugates. Angew. Chem. Int. Ed. 43, 6522-6525 (2004).
96. Kool, E. T.: Replacing the nucleobases in DNA with designer molecules. Acc. Chem. Res. 35, 936-943 (2002).
97. Onouchi, H., Miyagawa, T., Morino, K., Yashima, E.: Assisted formation of chiral porphyrin homoaggregates by an induced helical poly(phenylacetylene) template and their chiral memory. Angew. Chem. Int. Ed. 45, 2381-2384 (2006).
98. Li, C., Numata, M., Takeuchi, M., Shinkai, S.: A sensitive colorimetric and fluorescent probe based on a polythiophene derivative for the detection of ATP. Angew. Chem. Int. Ed. 44, 6371-6374 (2005).
99. Endo, M., Wang, H., Fujitsuka, M., Majima, T.: Pyrene-stacked nanostructures constructed in the recombinant tabacco mosaic virus rod scaffold. Chem. Eur. J. 12, 3735-3740 (2006).
100. Koti, A. S. R., Periasamy, N.: Self-assembly of template-directed J-aggregates of porphyrin. Chem. Mater. 15, 369-371 (2003).
101. Wang, M., Silva, G. L., Armitage, B. A.: DNA-templated formation of a helical cyanine dye J-aggregate. J. Am. Chem. Soc. 122, 9977-9986 (2000).
102. Renikuntala, B. R., Armitage, B. A.: Role reversal in a supramolecular assembly: a chiral cyanine dye controls the helicity of a peptide-nucleic acid duplex. Langmuir 21, 5362-5366 (2005).
103. Garoff, R. A., Litzinger, E. A., Connor, R. E., Fishman, I., Armitage, B. A.: Helical aggregation of cyanine dyes on DNA templates: effect of dye structure on formation of homo- and heteroaggregates. Langmuir 18, 6330-6337 (2002).
104. Aoki, K., Nakagawa, M., Ichimura, K.: Self-assembly of amphoteric azopyridine carboxylic acids: organized structures and macroscopic organized morphology influenced by heat, pH change, and light. J. Am. Chem. Soc. 122, 10997-11004 (2000).
105. Nakagawa, M., Ishii, D., Aoki, K., Seki, T., Iyoda, T.: Tubular and twisted Ni-P fibers molded from morphology-tunable and recyclable organic templates of hydrogen-bonded supramolecular assemblages. Adv. Mater. 17, 200-205 (2005).
106. Numata, M., Tamesue, S., Fujisawa, T., Haraguchi, S., Hasegawa, T., Bae, A.-H., Li, C., Sakurai, K., Shinkai, S.: β-1, 3-Glucan polysaccharide (schizophyllan) acting as a one-dimensional host for creating supramolecular dye assemblies. Org. Lett. 8, 5533-5536 (2006).
107. Hasegawa, T., Fujisawa, T., Numata, M., Li, C., Bae, A.-H., Haraguchi, S., Sakurai, K., Shinkai, S.: Schizophyllan acts as a one-dimensional host to accommodate 5, 10, 15, 20-tetrakis(4-carboxypheny)porphyrinatozinc acetate to produce its fibrous superstructure. Chem. Lett. 34, 1118-1119 (2005).
108. Kubo, Y., Kitada, Y., Wakabayashi, R., Kishida, T., Ayabe, M., Kaneko, K., Takeuchi, M., Shinkai, S.: A supramolecular bundling approach toward the alignment of conjugated polymers. Angew. Chem. Int. Ed. 45, 1548-1553 (2006).
109. Ikeda, M., Furusho, Y., Okoshi, K., Tanahara, S., Maeda, K., Nishino, S., Mori, T., Yashima, E.: A luminescent poly(phenylenevinylene)-amylose composite with supramolecular liquid crystallinity. Angew. Chem. Int. Ed. 45, 6491-6495 (2006).
110. Ewert, K. K., Evans, H. M., Zidovska, A., Bouxsein, N. F., Ahmad, A., Safinya, C. R.: A columnar phase of dendritic lipid-based cationic liposome-DNA complexes for gene delivery: hexagonally ordered cylindrical micelles embedded in a DNA honeycomb lattice. J. Am. Chem. Soc. 128, 3998-4006 (2006).
111. Numata, M., Sugikawa, K., Kaneko, K., Shinkai, S.: Creation of hierarchical carbon nanotube assemblies through alternative packing of complementary semi-artificial β-1, 3-glucan/carbon nanotube composites. Chem. Eur. J. 14, 2398-2404 (2007).
112. Schwab, A. D., Smith, D. E., Rich, C. S., Young, E. R., Smith, W. F., De Paula, J. C.: Porphyrin nanorods. J. Phys. Chem. B 107, 11339-11345 (2003).
113. Purrello, R., Bellacchio, E., Gurrieri, S., Lauceri, R., Raudio, A., Scolaro, L. M., Santoro, A. M.: pH Modulation of porphyrins self-assembly onto polylysine. J. Phys. Chem. B 102, 8852-8857 (1998).
114. Escudero, C., Crusats, J., Díez-Pérez, I., El-Hachemi, Z., Ribó, J. M.: Folding and hydrodynamic forces in J-aggregates of 5-phenyl-10, 15, 20-tris-(4-sulfophenyl)porphyrin. Angew. Chem. Int. Ed. 45, 8032-8035 (2006).
115. Hosomizu, K., Oodoi, M., Umeyama, T., Matano, Y., Yoshida, K., Isoda, S., Isosomppi, M., Tkachenko, N. V., Lemmetyinen, H., Imahori, H.: Substituent effects of porphyrins on structures and photophysical properties of amphiphilic porphyrin aggregates. J. Phys. Chem. B 112, 16517-16524 (2008).
116. Sugikawa, K., Numata, M., Kaneko, K., Sada, K., Shinkai, S.: Hierarchical polymer assemblies constructed by the mutual template effect of cationic polymer complex and anionic supramolecular nanofiber (to be submitted).
117. Numata, M., Fujisawa, T., Li, C., Haraguchi, S., Ikeda, M., Sakura, K., Shinkai, S.: β-1, 3-Glucan (schizophyllan) can act as a one-dimensional host for creating chirally twisted poly(p-phenylene ethynylene). Supramol. Chem. 19, 107-113 (2007).