Investigation of the Interaction Between Novel Spiro Thiazolo[3,2-a][1,3,5]Triazines and Bovine Serum Albumin by Spectro
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Investigation of the Interaction Between Novel Spiro Thiazolo[3,2-a][1,3,5]Triazines and Bovine Serum Albumin by Spectroscopic Methods Ying Yang • Xianyong Yu • Wenhua Tong • Shiyu Lu Heting Liu • Qin Yao • Hu Zhou
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Received: 23 February 2012 / Accepted: 11 August 2012 / Published online: 19 March 2013 Ó Springer Science+Business Media New York 2013
Abstract The interaction between novel spiro thiazolo[3,2-a][1,3,5]triazines (NSTT) and bovine serum albumin (BSA) was investigated using fluorescence and ultraviolet spectroscopy at different temperatures (302 and 310 K) under imitated physiological conditions. The experimental results show that the fluorescence quenching mechanism between NSTT and BSA is by a static quenching mechanism. The binding constant (Ka) and number of binding sites (n) between NSTT and BSA at different temperatures were obtained. Negative values of DG°, DH°, and DS° indicate that the interaction between NSTT and BSA is driven by hydrogen bonds and van der Waals forces. Using the Fo¨rster nonradiation energy transfer theory, the binding distance between BSA and NSTT was calculated. These results provide valuable information on the interaction between NSTT and BSA as well as the influence of substituent groups on the interaction. Keywords Novel spiro thiazolo[3,2-a][1,3,5]triazines Bovine serum albumin Fluorescence spectroscopy Absorption spectroscopy Interaction
1 Introduction Derivatives of spiropyrrolidines are found in a variety of biological applications such as antimicrobial, antitumoral, and antibiotic agents, and inhibitors of the human NK-1
Y. Yang X. Yu (&) S. Lu H. Liu Q. Yao H. Zhou (&) Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China e-mail: [email protected] H. Zhou e-mail: [email protected] W. Tong Department of Chemical Engineering, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China
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J Solution Chem (2013) 42:666–675 Scheme 1 Structures of novel spiro thiazolo[3,2-a] [1,3,5]triazines analogues
667
O N
O
N N
S Ar
N
Ar: 1 2 3 4 5
C 6H5; 4-CH3C6H4; 4-ClC6H4; 4-FC 6H4; 2,4-Cl2C6H3
receptor. Spiropyrrolidines are also motifs in some pharmacologically active alkaloids, such as rhynchophylline, corynoxeine, horsifiline, mitraphylline and spirotryprostatins [1–4]. As is well known, serum albumins (SA) contribute to colloid osmotic blood pressure and the maintenance of blood pH. They also play a dominant role in drug disposition and efficacy. Most drugs are transported as a complex with SA, which makes SA an important part of drug metabolism [5–7]. Bovine serum albumin (BSA) is a natural globular protein with a relatively high molecular mass (66.3 kDa) and a single polypeptide chain containing 585 amino acid residues. It consists of three linearly arranged and structurally distinct homo
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