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Improvement of Steroid Biotransformation with Hydroxypropyl-β-Cyclodextrin Induced Complexation

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Abstract

The inclusion complexes induced by cyclodextrins and its derivates have been shown previously to enhance the biotransformation of hydrophobic compounds. Using hydroxypropyl-β-cyclodextrin (HP-β-CD; 20% w/v), the water solubility of cortisone acetate increased from 0.039 to 7.382 g L−1 at 32 °C. The solubilization effect of HP-β-CD was far superior to dimethylformamide (DMF) and ethanol. The dissolution rate also significantly increased in the presence of HP-β-CD. The enzymatic stability of Δ1-dehydrogenase from Arthrobacter simplex TCCC 11037 was not influenced by the increasing concentrations of HP-β-CD contrary to the organic cosolvents which negatively influenced in the order DMF > ethanol. The activity inhibition effect caused by HP-β-CD was not so conspicuous as ethanol and DMF. Inactivation constants of ethanol, DMF, and HP-β-CD were 5.832, 4.541, and 1.216, respectively. The inactivation energy (E a) was in the order of HP-β-CD (55.1 kJ mol−1) > ethanol (39.9 kJ mol−1) > DMF (37.1 kJ mol−1).

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Abbreviations

CDs:

Cyclodextrins

HP-β-CD:

Hydroxypropyl-β-cyclodextrin

CA:

Cortisone acetate

PA:

Prednisone acetate

E a :

Inactivation energy

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

ESI-MS:

Electrospray ionization mass spectra

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Acknowledgments

This work is supported by National Natural Science Foundation of China (No. 20776111), which is gratefully acknowledged.

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Authors and Affiliations

  1. Key Laboratory of Industrial Microbiology, Ministry of Education, College of Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, People’s Republic of China

    Liting Zhang, Min Wang, Yanbing Shen, Yinhu Ma & Jianmei Luo

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  1. Liting Zhang
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Correspondence to Min Wang.

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Zhang, L., Wang, M., Shen, Y. et al. Improvement of Steroid Biotransformation with Hydroxypropyl-β-Cyclodextrin Induced Complexation. Appl Biochem Biotechnol 159, 642–654 (2009). https://doi.org/10.1007/s12010-008-8499-2

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