Spectroscopic, morphological, and mechanistic investigation of the solvent-promoted aggregation of porphyrins modified in meso-positions by glucosylated steroids

Chemistry - A European Journal

Volumn 17, Issue 49, 2011, Pages 13743-13753

  Zelenka, Karel ^a   Trnka, Tomáš ^a   Tišlerová, Iva ^a   Monti, Donato ^c   Cinti, Stefano ^c   Naitana, Mario Luigi ^c   Schiaffino, Luca ^c   Venanzi, Mariano ^c   Laguzzi, Giuseppe ^d   Luvidi, Loredana ^d   Mancini, Giovanna ^d   Nováková, Zdena ^b   Šimák, Ondřej ^b   Wimmer, Zdeněk ^e   Drašar, Pavel ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

^d SAPIENZA UNIVERSITY OF ROME   (Italy)

^e Institute of Experimental Botany AS CR Vvi   (Czech Republic)

Author keywords

aggregation; chirality; porphyrinoids; steroids; supramolecular chemistry

Indexed keywords

AFM; AGGREGATE MORPHOLOGY; AGGREGATION BEHAVIOURS; AGGREGATION MECHANISM; AGGREGATION PHENOMENA; AMPHIPHILICS; AQUEOUS SOLVENTS; BULK SOLVENTS; CONCENTRATION RANGES; DIMETHYL ACETAMIDE; EXPERIMENTAL EVIDENCE; FIBROUS STRUCTURES; GLOBULAR STRUCTURE; IN-LINE; MACROCYCLES; MESO POSITIONS; PORPHYRIN DERIVATIVES; PORPHYRINOIDS; ROD-SHAPED; SEMI-EMPIRICAL CALCULATION; STEROIDS; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR CHIRALITY; SUPRASTRUCTURES;

AGGLOMERATION; CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; COALESCENCE; CONCENTRATION (PROCESS); DICHROISM; ENANTIOMERS; FUNCTIONAL GROUPS; LIPIDS; NETWORK ARCHITECTURE; ORGANIC POLYMERS; SOLVENTS; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

PORPHYRINS;

GLYCOSIDE; PORPHYRIN; SOLVENT; STEROID; WATER;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; KINETICS; ULTRAVIOLET SPECTROPHOTOMETRY;

CIRCULAR DICHROISM; GLYCOSIDES; KINETICS; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; PORPHYRINS; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEROIDS; WATER;

EID: 82255191029     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101163     Document Type: Article

References (126)

1. Topics in Current Chemistry, Vol. 265, Supramolecular Chirality (Eds.:, M. Crego-Calama, D. N. Reinhoudt,), Springer, Berlin, 2006
2. M. A. Mateos-Timoneda, M. Crego-Calama, D. N. Reinhoudt, Chem. Soc. Rev. 2004, 33, 363-372
3. A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007, 119, 9106-9126
4. Angew. Chem. Int. Ed. 2007, 46, 8948-8968.
5. I. Occhiuto, G. De Luca, V. Villari, A. Romeo, N. Micali, R. F. Pasternack, L. Monsù Scolaro, Chem. Commun. 2011, 47, 6045-6047
6. R. F. Pasternack, E. J. Gibbs, D. Bruzewicz, D. Stewart, K. Shannon Engstrom, J. Am. Chem. Soc. 2002, 124, 3533-3539
7. J. Parkash, J. H. Robblee, J. Agnew, E. Gibbs, P. Collings, R. F. Pasternack, J. C. de Paula, Biophys. J. 1998, 74, 2089-2099
8. M. Balaz, M. De Napoli, A. E. Holmes, A. Mammana, K. Nakanishi, N. Berova, R. Purrello, Angew. Chem. 2005, 117, 4074-4077
9. Angew. Chem. Int. Ed. 2005, 44, 4006-4009
10. For "template-imprinted" chiral suprastructures and remarkable examples of "chiral memory", see:, R. Purrello, A. Raudino, L. Monsù Scolaro, A. Loisi, E. Bellacchio, R. Lauceri, J. Phys. Chem. B 2000, 104, 10900-10908
11. Scolaro, A. Loisi, E. Bellacchio, R. Lauceri, J. Phys. Chem. B 2000, 104, 10900-10908
12. E. Bellacchio, R. Lauceri, S. Guerrieri, L. Monsù Scolaro, A. Romeo, R. Purrello, J. Am. Chem. Soc. 1998, 120, 12353-12354
13. A. Mammana, A. D'Urso, R. Lauceri, R. Purrello, J. Am. Chem. Soc. 2007, 129, 8062-8063
14. G. De Luca, A. Romeo, L. Monsù Scolaro, R. F. Pasternack, Chem. Commun. 2010, 46, 389-391.
15. Y. Kubo, Y. Ishii, T. Yoshizawa, S. Tokita, Chem. Commun. 2004, 1394-1395
16. D. Monti, L. La Monica, A. Scipioni, G. Mancini, New J. Chem. 2001, 25, 780-782
17. V. V. Borovkov, T. Harada, G. A. Hembury, Y. Inoue, R. Kuroda, Angew. Chem. 2003, 115, 1788-1791
18. Angew. Chem. Int. Ed. 2003, 42, 1746-1749
19. G. Pescitelli, S. Gabriel, Y. Wang, J. Fleischhauer, R. W. Woody, N. Berova, J. Am. Chem. Soc. 2003, 125, 7613-7628, and references therein.
20. J. M. Ribõ, J. Crusats, F. Sagués, J. Claret, R. Rubires, Science 2001, 292, 2063-2066
21. R. Rubires, J.-A. Farrera J. M. Ribõ, Chem. Eur. J. 2001, 7, 436-446
22. A. Tsuda, Md. A. Alam, T. Harada, T. Yamaguchi, N. Ishii, T. Aida, Angew. Chem. 2007, 119, 8346-8350
23. Angew. Chem. Int. Ed. 2007, 46, 8198-8202
24. T. Yamaguchi, T. Kimura, H. Matsuda, T. Aida, Angew. Chem. 2004, 116, 6510-6515
25. Angew. Chem. Int. Ed. 2004, 43, 6350-6355.
26. L. Zeng, Y. He, Z. Dai, J. Wang, Q. Cao, Y. Zhang, ChemPhysChem 2009, 10, 954-962.
27. Y. Zhang, P. Chen, M. Liu, Chem. Eur. J. 2008, 14, 1793-1803
28. P. Chen, X. Ma, P. Duan, M. Liu, ChemPhysChem 2006, 7, 2419-2423
29. Y. Qiu, P. Chen, M. Liu, Langmuir 2010, 26, 15272-15277.
30. Z. El-Hachemi, G. Mancini, J. M. Ribõ, A. Sorrenti, J. Am. Chem. Soc. 2008, 130, 15176-15184.
31. D. Monti, M. De Rossi, A. Sorrenti, G. Laguzzi, E. Gatto, M. Stefanelli, M. Venanzi, L. Luvidi, G. Mancini, R. Paolesse, Chem. Eur. J. 2010, 16, 860-870
32. D. Monti, M. Venanzi, M. Stefanelli, A. Sorrenti, G. Mancini, C. Di Natale, R. Paolesse, J. Am. Chem. Soc. 2007, 129, 6688-6689
33. D. Monti, M. Venanzi, G. Mancini, C. Di Natale, R. Paolesse, Chem. Commun. 2005, 2471-2473
34. D. Monti, V. Cantonetti, M. Venanzi, F. Ceccacci, C. Bombelli, G. Mancini, Chem. Commun. 2004, 972-973. Studies on the aggregation of related chiral porphyrin derivatives have been recently reported by others. See, for example
35. P. Iavicoli, M. Simõn-Sorbed, D. B. Amabilino, New J. Chem. 2009, 33, 358-365
36. P. Iavicoli, H. Xu, L. N. Feldborg, M. Linares, S. Stafsrtöm, C. Ocal, B. Nieto-Ortega, J. Casado, J. T. Lõpez Navarrete, R. Lazzaroni, S. De Feyter, D. B. Amabilino, J. Am. Chem. Soc. 2010, 132, 9350-9362. Porphyrin-substituted nucleotides have been recently reported to successfully implement into helical DNA scaffolds
37. I. Bouamaied, T. N. Nguyen, T. Rühl, E. Stulz, Org. Biomol. Chem. 2008, 6, 3888-3891.
38. P. Štěpánek, M. Dukh, D. Šaman, J. Moravcová, L. Kniežo, D. Monti, M. Venanzi, G. Mancini, P. Drašar, Org. Biomol. Chem. 2007, 5, 960-970
39. D. Monti, E. Gatto, M. Venanzi, G. Mancini, A. Sorrenti, P. Štěpánek, P. Drašar, New J. Chem. 2008, 32, 2127-2133. For other related studies, see
40. C. Schell, H. K. Hombrecher, Chem. Eur. J. 1999, 5, 587-598
41. M. Dukh, P. Drašar, I. Černý, V. Pouzar, J. A. Shriver, J. L. Sessler, Supramol. Chem. 2002, 14, 237-244
42. M. Dukh, D. Šaman, J. Kroulík, I. Černý, V. Pouzar, V. Král, P. Drašar, Tetrahedron 2003, 59, 4069-4076
43. N. T. T. Huong, P. Klímková, A. Sorrenti, G. Mancini, P. Drašar, Steroids 2009, 74, 715-720
44. P. Štěpánek, O. Šimák, Z. Novákova, Z. Wimmer, P. Drašar, Org. Biomol. Chem. 2011, 9, 682-683.
45. R. Fong, D. I. Schuster, S. R. Wilson, Org. Lett. 1999, 1, 729-732
46. T. S. Balaban, N. Berova, C. M. Drain, R. Hauschild, X. Huang, H. Kalt, S. Lebedkin, J.-M. Lehn, F. Nifaitis, G. Pescitelli, V. I. Prokhorenko, G. Riedel, G. Smeureanu, J. Zeller, Chem. Eur. J. 2007, 13, 8411-8427.
47. S.-H. Chen, H. Zhu, B. Liu, H. Zhao, Youji Huaxue 1988, 8, 34-36
48. S.-H. Chen, Y. Chen, H.-G. Li, Huaxue Xuebao 1997, 44, 716-722.
49. M. Dukh, D. Šaman, K. Lang, V. Pouzar, I. Černý, P. Drašar, V. Král, Org. Biomol. Chem. 2003, 1, 3458-3463.
50. E. Girgenti, R. Ricoux, J.-P. Mahy, Tetrahedron 2004, 60, 10049-10058.
51. Y. Li, J. R. Dias, Chem. Rev. 1997, 97, 283-304.
52. J. T. Groves, R. Neumann, J. Am. Chem. Soc. 1989, 111, 2900-2909
53. J. Lahiri, G. D. Fate, S. B. Ungashe, J. T. Groves, J. Am. Chem. Soc. 1996, 118, 2347-2358
54. For other examples of P450 mimics see, for example:, D. Monti, P. Tagliatesta, G. Mancini, T. Boschi, Angew. Chem. 1998, 110, 1154-1156
55. Angew. Chem. Int. Ed. Engl. 1998, 37, 1131-1133
56. S. Borocci, F. Marotti, G. Mancini, D. Monti, A. Pastorini, Langmuir 2001, 17, 7198-7203
57. V. Cantonetti, D. Monti, M. Venanzi, C. Bombelli, F. Ceccacci, G. Mancini, Tetrahedron: Asymmetry 2004, 15, 1969-1977.
58. L. G. Mackay, R. P. Bonar-Law, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1993, 1377-1378
59. R. P. Bonar-Law, L. G. Mackay, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1993, 456-458
60. R. P. Bonar-Law, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 3085-3096
61. R. P. Bonar-Law, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1991, 574-577.
62. S. Tomas, L. Milanesi, J. Am. Chem. Soc. 2009, 131, 6618-6623
63. B.-W. Liu, Y. Chen, B.-E. Song, Y. Liu, Chem. Commun. 2011, 47, 4418-4420
64. For a recent overview on the application of porphyrin derivatives in chemical sensors, see:, R. Paolesse, D. Monti, S. Nardis, C. Di Natale, in The Handbook of Porphyrin Science, Vol. 12 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific, London, 2010, Chapter 54, pp. 121-226.
65. M.-C. Desroches, A. Kasselouri, M. Meyniel, P. Fontaine, M. Goldmann, P. Prognon, P. Maillard, V. Rosilio, Langmuir 2004, 20, 11698-11705
66. A. Lavi, H. Weitman, R. T. Holmes, K. M. Smith, B. Ehrenberg, Biophys. J. 2002, 82, 2101-2110
67. S. Ferro, F. Ricchelli, D. Monti, G. Mancini, G. Jori, Int. J. Biochem. Cell Biol. 2007, 39, 1026-1034
68. For an overview on the application of porphyrin derivatives as therapeutic agents, see:, R. K. Pandey, G. Zheng, in The Porphyrin Handbook, Vol. 6 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic, New York, 2000, Chapter 43, pp. 157-230.
69. K. Zelenka, T. Trnka, I. Tišlerová, V Král. M. Dukh, P. Drašar, Coll. Czech. Chem. Commun. 2004, 69, 1149-1160.
70. R. F. Pasternack, P. J. Collings, Science 1995, 269, 935-939.
71. S. Allenmark, Chirality 2003, 15, 409-422, and references therein
72. Formation of chiral supramolecular systems as a consequence of interaction of achiral dendritic macromolecules with chiral ionic cholesteric groups was recently reported:, A. J. Soininen, E. Kasëmi, A. D. Schlüter, O. Ikkala, J. Ruokolainen, R. Mezzenga, J. Am. Chem. Soc. 2010, 132, 10882-10890.
73. F. Helmich, C. C. Lee, M. M. L. Niewenhuizen, J. C. Gielen, P. C. M. Christianen, A. Larsen, G. Fytas, P. E. L. G. Leclere, A. P. H. J. Schenning, E. W. Meijer, Angew. Chem. 2010, 122, 4031-4034
74. Angew. Chem. Int. Ed. 2010, 49, 3939-3942
75. G. De Luca, A. Romeo, V. Villari, N. Micali, I. Foltran, E. Foresti, I. G. Lesci, N. Roveri, T. Zuccheri, L. Monsù Scolaro, J. Am. Chem. Soc. 2009, 131, 6920-6921
76. N. C. Maiti, S. Mazumdar, N. Periasamy, J. Porphyrins Phthalocyanines 1998, 2, 369-376.
77. X. W. Li, D. J. Li, W. F. Zeng, G. L. Zou, Z. P. Chen, J. Phys. Chem. B 2007, 111, 1502-1506.
78. V. V. Borovkov, G. A. Hembury, Y. Inoue, Acc. Chem. Res. 2004, 37, 449-459.
79. N. Berova, K. Nakanishi, in Circular Dichroism. Principles and Applications, 2 nd ed., (Eds.: N. Berova, K. Nakanishi, R. W. Woody,), Wiley, New York, 2000. p. 337-382.
80. C. Reichardt, Solvents and Solvents Effects in Organic Chemistry, 3 rd ed., Wiley-VCH, Weinheim, 2004
81. M. H. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1990, 521-529.
82. R. F. Pasternack, E. J. Gibbs, P. J. Collings, J. C. dePaula, L. C. Turzo, A. Terracina, J. Am. Chem. Soc. 1998, 120, 5873-5878.
83. The term extinction is more appropriate than absorbance, because of the presence of RLS scattering contribution to UV/Vis bands. See, for example, N. Micali, F. Mallamace, M. Castriciano, A. Romeo, L. Monsú Scolaro, Anal. Chem. 2001, 73, 4958-4963.
84. A different interpretation of the meaning of the parameter m has been offered by others, for the formation of small aggregates of benzoporphyrin derivatives (DiesterB) in aqueous solvent mixtures. It was proposed that this value accounts not only for the nucleus size, but also for their quantity formed in the first lag period:, F. I. Simplicio, R. Ribeiro da Silva Soares, F. Maionchi, O. S. Filho, N. Hioka, J. Phys. Chem. A 2004, 108, 9384-9389.
85. R. F. Pasternack, C. Fleming, S. Herring, P. J. Collings, J. C. dePaula, J. DeCastro, E. J. Gibbs, Biophys. J. 2000, 79, 550-560
86. M. A. Castriciano, A. Romeo, L. Monsù Scolaro, J. Porphyrins Phthalocyanines 2002, 6, 431-438.
87. L. Monsù Scolaro, M. A. Castriciano, A. Romeo, A. Mazzaglia, F. Mallamace, N. Micali, Physica A 2002, 304, 158-169.
88. N. Micali, V. Villari, M. A. Castriciano, A. Romeo, L. Monsù Scolaro, J. Phys. Chem. B 2006, 110, 8289-8295.
89. P. Donovan, A. Robin, M. S. Dyer, M. Perrson, R. Raval, Chem. Eur. J. 2010, 16, 11641-11652
90. M. Koepf, J. A. Wytko, J.-P. Bucher, J. Weiss, J. Am. Chem. Soc. 2008, 130, 9994-10001
91. M. Scarselli, G. Ercolani, P. Castrucci, D. Monti, G. Bussetti, M. Russo, C. Goletti, P. Chiaradia, R. Paolesse, M. De Crescenzi, Surf. Sci. 2007, 601, 2607-2610, and references therein. This is found, however, mostly for "bare" aryl porphyrins; in the case of supramolecular species held by more complex intermolecular interactions, the effect of the surface is less relevant. See, for example
92. A. D. Schwab, D. E. Smith, C. S. Rich, E. R. Young, W. F. Smith, J. C. de Paula, J. Phys. Chem. B 2003, 107, 11339-11345
93. J. A. A. W. Elemans, R. van Hameren, R. J. M. Nolte, A. E. Rowan, Adv. Mater. 2006, 18, 1251-1266
94. J. Otsuki, E. Nagamine, T. Kondo, K. Iwasaki, M. Asakawa, K. Miyake, J. Am. Chem. Soc. 2005, 127, 10400-10405.
95. Y. Qiu, P. Chen, M. Liu, J. Am. Chem. Soc. 2010, 132, 9644-9652. The process of fibrillogenesis is of importance in investigations of the mechanism of formation of amyloid structures. See, for example
96. D. M. Walsh, A. Lomakin, G. B. Benedek, M. M. Condron, D. B. Teplow, J. Biol. Chem. 1997, 272, 22364-22372
97. I. W. Hamley, Angew. Chem. 2007, 119, 8274-8295
98. Angew. Chem. Int. Ed. 2007, 46, 8128-8147, and references therein.
99. X. Gong, T. Milic, C. Xu, J. D. Batteas, C. M. Drain, J. Am. Chem. Soc. 2002, 124, 14290-14291
100. C. M. Drain, G. Smeureanu, S. Patel, X. Gong, J. Garno, J. Arijeloye, New J. Chem. 2006, 30, 1834-1843
101. G. Smeureanu, A. Aggarwal, C. E. Soll, J. Arijeloye, E. Malave, C. M. Drain, Chem. Eur. J. 2009, 15, 12133-12140.
102. T. S. Balaban, A. D. Bhise, M. Fisher, M. Linke-Schaetzel, C. Roussel, N. Vanthuyne, Angew. Chem. 2003, 115, 2190-2194
103. Angew. Chem. Int. Ed. 2003, 42, 2140-2144
104. T. S. Balaban, M. Linke-Schaetzel, A. D. Bhise, N. Vanthuyne, C. Roussel, Eur. J. Org. Chem. 2004, 3919-3930
105. T. S. Balaban, Acc. Chem. Res. 2005, 38, 612-623.
106. J. Wu, T. Yi, Y. Zou, F. Liu, J. Dong, T. Shu, F. Li, C. Huang, Chem. Eur. J. 2009, 15, 6234-6243
107. J. H. Jung, S.-H. Lee, J. S. Yoo, K. Yoshida, T. Shimizu, S. Shinkai, Chem. Eur. J. 2003, 9, 5307-5313
108. O. Gronwald, S. Shinkai, Chem. Eur. J. 2001, 7, 4328-4334
109. M. Numata, S. Shinkai, Chem. Commun. 2011, 47, 1961-1975.
110. J. J. P. Stewart, J. Mol. Model. 2007, 13, 1173-1213.
111. J. J. P. Stewart, MOPAC2009, Stewart Computational Chemistry, Colorado Springs, CO, USA, 2008,.
112. D. Filippini, A. Alimelli, C. Di Natale, R. Paolesse, A. D'Amico, I. Lundström, Angew. Chem. 2006, 118, 3884-3887
113. Angew. Chem. Int. Ed. 2006, 45, 3800-3803
114. D. Filippini, C. Di Natale, R. Paolesse, A. D'Amico, I. Lundstrom, Sens. Actuators B 2007, 121, 93-102
115. R. Paolesse, F. Mandoj, A. Marini, C. Di Natale, in Encyclopedia of Nanoscience and Nanotechnology, Vol. 9 (Ed.:, H. Nalwa,), American Science, Valencia CA (USA), 2004, p. 21.
116. L. Lvova, E. Martinelli, E. Mazzone, A. Pede, R. Paolesse, C. Di Natale, A. D'Amico, Talanta 2006, 70, 833-839.
117. R. Paolesse, D. Monti, L. La Monica, M. Venanzi, A. Froiio, S. Nardis, C. Di Natale, E. Martinelli, A. D'Amico, Chem. Eur. J. 2002, 8, 2476-2483
118. R. Purrello, S. Guerrieri, R. Lauceri, Coord. Chem. Rev. 1999, 190-192, 683-706
119. L. S. Dolci, E. Marzocchi, M. Montalti, L. Prodi, D. Monti, C. Di Natale, A. D'Amico, R. Paolesse, Biosens. Bioelectron. 2006, 22, 399-404
120. Y. Miura, T. Yamauchi, H. Sato, T. Fukuda, Thin Solid Films 2008, 516, 2443-2449
121. M. Trojanowicz, M. Kaniewska, Electroanalysis 2009, 21, 229-238
122. For a review on chirality-sensing supramolecular systems, see:, G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73.
123. Organogel systems based on porphyrin-sugar conjugates were shown to be suitable for the construction of chiral inorganic materials:, S.-I. Kawano, S.-I. Tamaru, N. Fujita, S. Shinkai, Chem. Eur. J. 2004, 10, 343-351.
124. T. Mallat, E. Orglmeister, A. Baiker, Chem. Rev. 2007, 107, 4863-4890
125. C. Li, H. Zhang, D. Jiang, Q. Yang, Chem. Commun. 2007, 547-558.
126. A. Rumlerova-Lipsová, J. Barek, P. Drasar, K. Zelenka, K. Pecková, Int. J. Electrochem. Sci. 2007, 2, 235-247, and references therein.