Abstract
Aggregation, catalytic activity, and the influence of alkylated p-sulfonatocalix[n]arenes (SCA; n = 4, 6, 8) on the energy exchange in cells of wheat roots were studied. In water SCA are surfactants, and their efficiency changes with an increase in the number of aromatic rings (n) and the length of hydrocarbon substituents (R) in the molecule. In the range of critical micelle concentration, SCA form micelles with an effective hydrodynamic diameter of ∼200 nm. The catalytic activity of micellar solutions of SCA (n = 4, 8; R = C12H25) in hydrolysis of ethyl 4-nitrophenyl chloromethylphosphonate (ENCP) decreases with an increase in n, whereas the binding constant of ENCP increases. The modifying effect of SCA on the membranes and the energy exchange in cells of wheat roots was revealed: the membranotropic activity of SCA increases with an increase in the hydrophobicity of substituents R and the macrocycle size.
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J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley & Sons, New York, 2000.
Calixarenes in Action, Eds L. Mandolini, R. Ungaro, Imperial College Press, London, 2000, 271 pp.
S. Shinkai, S. Mori, T. Tsubaki, T. Sone, O. Monabe, Tetrahedron Lett., 1984, 25, 5315.
S. Shinkai, S. Mori, H. Koreishi, T. Tsubaki, O. Monabe, J. Am. Chem. Soc., 1986, 108, 2409.
C. D. Gutsche, I. Alam, Tetrahedron, 1988, 44, 4689.
A. W. Coleman, S. G. Bott, S. D. Morley, C. M. Means, K. D. Robinson, H. Zhang, J. L. Atwood, Angew. Chem., 1988, 27, 1361.
S. Shinkai, T. Arimura, K. Araki, H. Kawabata, J. Chem. Soc., Perkin Trans. 1, 1989, 2039.
M. Komiyama, K. Isaka, S. Shinkai, Chem. Lett., 1991, 937.
J.-P. Scharff, M. Mahjoubi, New. J. Chem., 1991, 15, 883.
J. L. Atwood, D. L. Clark, R. K. Juneja, G. W. Orr, K. D. Robinson, R. L. Vincent, J. Am. Chem. Soc., 1992, 114, 7558.
G. Arena, R. Cali, G. G. Lombardo, E. Rizzarelli, D. Sciotto, Supramol. Chem., 1992, 1, 19.
A. Ikeda, S. Shinkai, Chem. Rev., 1997, 97, 1713.
J. Alvarez, Y. Wang, M. Gomez-Kaifer, A. E. Kaifer, Chem. Commun., 1998, 1455.
E. A. Karakhanov, T. S. Buchneva, A. L. Maksimov, E. A. Runova, Neftekhimiya, 2003, 43, 42 [Petrochemistry (Engl. Transl.), 2003, 43].
I. S. Millership, J. Incl. Phenom., 2001, 39, 327.
A. S. Lobach, I. S. Ryzhkina, N. G. Spitsina, E. D. Obraztsova, Phys. Stat. Sol. (b), 2007, 244, 4030.
F. Perret, A. N. Lazar, A. W. Coleman, Chem. Commun., 2006, 2425.
A. Specht, Ph. Bernard, M. Goldner, L. Peng, Angew. Chem., Int. Ed. Engl., 2002, 41, 4706.
B. V. Passet, Osnovnye protsessy khimicheskogo sinteza biologicheski aktivnykh veshchestv [The Main Processes of Chemical Synthesis of Biologically Active Substances], GEOTAR-MED, Moscow, 2002, 376 (in Russian).
J. J. Lundquist, E. J. Toone, Chem. Rev., 2002, 102, 555.
Kh. Kasumov, J. Bolard, Pol. J. Chem., 2004, 78, 1057.
I. S. Ryzhkina, W. D. Habicher, Yu. V. Kiseleva, A. P. Timosheva, A. I. Konovalov, Yu. N. Valitova, G. N. Mardanova, A. N. Tsentsevitskii, L. Kh. Gordon, Dokl. Akad. Nauk, 2007, 413, 557 [Dokl. Biochem. Biophys., 2007, 413, 68].
K. Holmberg, B. Jonsson, B. Kronberg, B. Lindman, Surfactants and Polymers in Aqueous Solutions, 2nd ed., J. Wiley & Sons, New York, 2003.
Signalling through Protein Phosphatases, Eds J. Arino, D. R. Alexander, S. Hohmann, Springer-Verlag, Heidelberg, 2004.
E. Fendler, J. Fendler, in Advances in Physical Organic Chemistry, Ed. V. Gold, Academic Press, New York, 1970, 8.
I. S. Ryzhkina, T. N. Pashirova, W. D. Habicher, L. A. Kudryavtseva, A. I. Konovalov, Macromolecular Symposia: Reactive Polymers 2003, Dresden, Germany, September 28–October 1, 2003, Ed. H.-J. P. Adler, Wiley-VCH Verlag GmbH & Co., Weinheim, 2004, 41.
I. S. Ryzhkina, L. A. Kudryavtseva, Ya. A. Babkina, K. M. Enikeev, M. A. Pudovik, A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 2000, 1361 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1355].
I. S. Ryzhkina, Ya. A. Babkina, S. S. Lukashenko, K. M. Enikeev, L. A. Kudryavtseva, A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 2002, 2026 [Russ. Chem. Bull., Int. Ed., 2002, 51, 2183].
N. O. Mchedlov-Petrosyan, Differentsirovanie sily organicheskikh kislot v istinnykh i organizovannykh rastvorakh [Differentiation of Strength of Organic Acids in True and Organized Solutions], Izd. Kharkov Nat. Univ., Kharkov, 2004, 326 (in Russian).
A. Himoe, K. G. Brandt, R. J. DeSa, G. P. Hess, J. Biol. Chem., 1969, 244, 3483.
Yu. N. Valitova, A. I. Khairova, L. Kh. Gordon, Yu. V. Kiseleva, I. S. Ryzhkina, S. E. Solov’eva, L. M. Pilishkina, in Mater. Vseros. Nauch. Konf. “Ustoichivost’ rastenii k neblagopriyatnym faktoram vneshnei sredy” [Proc. All-Russia Scientific Conf. “Resistance of Plants to Unfavorable Environmental Factors”], Irkutsk, 2007, 44 (in Russian).
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2424–2429, December, 2009.
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Ryzhkina, I.S., Kiseleva, Y.V., Solov’eva, S.E. et al. Supramolecular systems based on alkylated p-sulfonatocalix[n]arenes: aggregation and catalytic and biological activity. Russ Chem Bull 58, 2506–2511 (2009). https://doi.org/10.1007/s11172-009-0351-5
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DOI: https://doi.org/10.1007/s11172-009-0351-5