title: Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy.
abstract: In the present study, 3-(fluorobenzylideneamino)-6-chloro-1-(3,3-dimethylbutanoyl)-phenyl-2,3-dihydroquinazolin-4(1H)-one (FDQL) derivatives have been designed and synthesized to study the interaction between fluorine substituted dihydroquinazoline derivatives with human serum albumin (HSA) using fluorescence, circular dichroism and Fourier transform infrared spectroscopy. The results indicated that the FDQL could bind to HSA, induce conformation and the secondary structure changes of HSA, and quench the intrinsic fluorescence of HSA through a static quenching mechanism. The thermodynamic parameters, ΔH, ΔS, and ΔG, calculated at different temperatures, revealed that the binding was through spontaneous and hydrophobic forces and thus played major roles in the association. Based on the number of binding sites, it was considered that one molecule of FDQL could bind to a single site of HSA. Site marker competition experiments indicated that the reactive site of HSA to FDQL mainly located in site II (subdomain IIIA). The substitution by fluorine in the benzene ring could increase the interactions between FDQL and HSA to some extent in the proper temperature range through hydrophobic effect, and the substitution at meta-position enhanced the affinity greater than that at para- and ortho-positions.
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. wangyi@ahau.edu.cn.|Department of Applied Chemistry, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. wangyi@ahau.edu.cn.
authors.forename: Yi
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. zhumeiqing@ahau.edu.cn.
authors.forename: Meiqing
authors.initials: M
authors.lastname: Zhu
authors.affiliation: Department of Applied Chemistry, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. caulf0527@163.com.
authors.forename: Feng
authors.initials: F
authors.lastname: Liu
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. wxw@ahau.edu.cn.
authors.forename: Xiangwei
authors.initials: X
authors.lastname: Wu
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. dandanpan@ahau.edu.cn.
authors.forename: Dandan
authors.initials: D
authors.lastname: Pan
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. ljia198346@163.com.|Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou 450002, China. ljia198346@163.com.
authors.forename: Jia
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. fanshisuo@ahau.edu.cn.
authors.forename: Shisuo
authors.initials: S
authors.lastname: Fan
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. zwang@ahau.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. tangjun@ahau.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Tang
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. risongna@163.com.|Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou 450002, China. risongna@163.com.
authors.forename: Risong
authors.initials: R
authors.lastname: Na
authors.affiliation: Department of Molecular Biosciences and Bioengineering, University of Hawaii, 1955 East-West Road, Honolulu, HI 96822, USA. qingl@hawaii.edu.
authors.forename: Qing X
authors.initials: QX
authors.lastname: Li
authors.affiliation: Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, Hefei 230036, China. rimaohua@ahau.edu.cn.
authors.forename: Rimao
authors.initials: R
authors.lastname: Hua
authors.affiliation: Department of Applied Chemistry, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China. shangzho@cau.edu.cn.
authors.forename: Shangzhong
authors.initials: S
authors.lastname: Liu
mesh_terms: D002942:Circular Dichroism; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D011485:Protein Binding; D017433:Protein Structure, Secondary; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012709:Serum Albumin / Q000737:chemistry* / Q000378:metabolism*; D013050:Spectrometry, Fluorescence; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
chemical_list: D015363:Quinolones; D012709:Serum Albumin
keywords: FDQL; fluorescence quenching; fluorine; human serum albumin; synthesis