pH Independent Complexation of 2-Aminobenzimidazole with β-cyclodextrin

Document Type: Research Paper

Authors

1 Centre for Nanoscience and Technology Pondicherry University

2 Chemistry Section, FEAT, Annamalai University, Annamalainagar 608 002, India

3 International Research Centre, Kalasalingam University, Krishnankoil

4 Department of Chemistry, SCSVM University, Enathur, Kanchipuram

Abstract

The spectral characteristics of 2-aminobenzimidazole (2ABZ) in aqueous and β-cyclodextrin media has been investigated using absorption, steady state and time resolved fluorescence techniques. The stoichiometric ratio of the inclusion complex of neutral and monocationic forms of 2ABZ in β-CDx medium is found to be 1:1. There is no significant differences between ground and the excited state pKa values of 2ABZ under both the media and thus the amino group of 2ABZ molecule is not much affected by the complexation process i.e., it lies outside the β-CDx cavity. Considering the shape and dimensions of β-CDx, it is clear that the 2ABZ molecule cannot be completely included in the β-CDx cavity. Because, the overall height of 2ABZ is 10.6 Å, but the overall height of β-CDx is only 7.8 Å. Hence, it is possible to locate half of the 2ABZ molecule only permitted inside the β-CDx cavity as interpreted using experimental data.

Keywords


[1]       R.P. Sijbesma, F.H. Beijer, L. Brunsveld, B.J. Folmer, J.H. Hirschberg, R.F. Lange, J.K. Lowe, E.W. Meijer, Science 278 (1997) 1601.

[2]       T. Park, S.C. Zimmerman, S. Nakashima, J. Am. Chem. Soc 127 (2005) 6520.

[3]       J.H. Ryu, D.J. Hong, M. Lee, Chem. Commun 127 (2008) 1043.

[4]       J.D. Hartgerink, E. Beniash, S.I. Stupp, Science 294 (2001) 1684.

 

 

[5]       Z. Zhang, Y. Luo, J. Chen, S. Dong, Y. Yu, Z. Ma, F. Huang, Angew. Chem. Int. Ed. 50 (2011) 1397.

[6]       K. Ariga, T. Kunitake, Springer-Verlag, Berlin, Heidelberg, New York, 2006.

[7]       H.J. Schneider, Taylor & Francis: Boca   Raton, FL. (2012).

[8]       F. Wang, J. Zhang, X. Ding, S. Dong, M. Liu, B. Zheng, S. Li, L. Wu, Y. Yu, H.W. Gibson, F. Huang, Angew. Chem. Int. Ed. 49 (2010) 1090.

[9]       W. Zhang, W. Jin, T. Fukushima, A. Saeki, S. Seki, T. Aida, Science 334 (2011) 340.

[10]    F. Wang, C. Han, C. He, Q. Zhou, J. Zhang, C. Wang, N. Li, F. Huang, J. Am. Chem. Soc. 130 (2008) 11254.

[11]    B. Rybtchinski, ACS Nano 5 (2011) 6791.

[12]    K.E. Schmalenberg, L. Frauchiger, L. Nikkhouy-Albers, K.E. Uhrich, Biomacromol. 2(2001) 851.

[13]    T. Govender, T. Riley, T. Ehtezazi, M.C. Garnett, S. Stolnik, L. Illum, S.S. Davis, Int. J. Pharm. 199 (2000) 95.

[14]    K. Ariga, T. Kunitake, Springer-Verlag, Berlin, Heidelberg, New York, 2006.

[15]    J. Szejtli, Chem. Rev. 98 (1998) 1743.

[16]    S.J. Lee, W. Lin, Acc. Chem. Res. 41 (2008) 521.

[17]    M.V. Rekharsky, Y. Inoue, Chem. Rev. 98 (1998) 1875.

[18]    M.V. Rekharsky, Y. Inoue, J. Am. Chem. Soc. 124 (2002) 813.

[19]    T.  Irie,   K.   Uekama,  Adv.  Drug  Delivery  Rev.  36

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

(1999) 101.

[20]    S.A. Nepogodiev, J.F. Stoddart, Chem. Rev. 98 (1998) 1959.

[21]    G. Wenz, B.H. Han, A. Müller, Chem. Rev. 106 (2006) 782.

[22]    Y. Liu, Y.L. Zhao, H.Y. Zhang, H.B. Song, Angew. Chem. Int. Ed. 115 (2003) 3382.

[23]    J. Araki, K. Ito, Soft Matter 3 (2007) 1456.

[24]    H. Chapman, In “Dictionary of Organic Compounds, Vth Ed, New York, London, Toronto, 1982.

[25]    C. Zhang, G. Vasmatzis, J.L. Cornette, C.  DeLisi, J. Mol. Biol. 267 (1997) 707.

[26]    D. Schneidman-Duhovny, Y. Inbar, R. Nussinov, H.J. Wolfson, Nucl. Acids Res. 33 (2005) 363.

[27]    M.L. Connolly, Science 221 (1983) 709.

[28]    D.W. Cho, Y.H. Kim, S.G. Koug, M. Yoon, D.J. Kim, J. Chem. Soc. Faraday Trans. 92 (1996) 29.

[29]    H.A. Benesi, J.H. Hildebrand, J. Am. Chem. Soc. 71 (1949) 2703.

[30]    S. Monti, G. Kohler, G. Grabner, J. Phys. Chem. 97 (1993) 13011.

[31]    D. Duhovny, R. Nussinov, H.J. Wolfson, Proceedings of the Second Workshopon Algorithms in Bioinformatics (WABI), Lecture Notes in Computer Science Rome, Italy: Springer Verlag 2452 (2002) 185.

[32]    C. Zhang, G. Vasmatzis, J.L. Cornette, C. DeLisi, J. Mol. Biol. 267 (1997) 707.