|
|
|
|
|
|
| Study on the Interaction Between Dehydronorcantharidin Imide-Cinnamaldehyde and Human Serum Albumin by Spectroscopy and Molecular Docking Simulation |
| ZENG Zao, ZHANG Hao, FAN Yi-ning, YAN Jin-ling |
School of Chemical Engineering, Guizhou University of Engineering Science, Bijie 551700, China
|
|
|
|
|
Abstract Dehydronorcantharidin compounds are a class of drugs with anticancer activity. The interaction mechanism between compounds and human serum albumin (HSA) is of great significance for understanding the properties of such drugs. In this study, dehydronorcantharidin imide-cinnamaldehyde (DCIC) was synthesized from furan, cinnamaldehyde and maleic anhydride, and the structure of the target compound was confirmed by NMR spectroscopy. The interaction mechanism of DCIC with HSA was investigated using fluorescence spectroscopy, site marker competition and molecular docking simulations. Fluorescence spectroscopy results indicated that the quenching mechanism of DCIC towards HSA followed a static quenching model. The quenching constants at 298, 303, and 313 K were found to be 8.53×104, 7.05×104, and 6.05×104 L·mol-1, respectively. At 303 K, the number of binding sites was calculated to be 0.978, and the Gibbs free energy is -25.75 kJ·mol-1. Both the enthalpy change (ΔH) and entropy change (ΔS) were negative, suggesting that the main interaction forces between DCIC and HSA were hydrogen bonds and van der Waals forces. According to Förster's theory of energy transfer, the binding distance between DCIC and HSA was calculated to be 3.946 nm, which is less than 7 nm, indicating static quenching through non-radiative energy transfer. Synchronous fluorescence spectroscopy results further revealed that DCIC increased the hydrophobicity of the microenvironment surrounding the tryptophan residue. Molecular docking simulations showed that DCIC binds to HSA at site I through a hydrogen bond, with an optimal binding energy of -25.44 kJ·mol-1, which is consistent with the findings from the spectroscopic and site competition experiments. This study provides a crucial theoretical foundation for research on the storage, transport, and pharmacokinetics of DCIC within the human body.
|
|
Received: 2025-01-25
Accepted: 2025-07-13
|
|
|
|
[1] LIU Fu-long, JIANG Tao, ZUO Dai-shu, et al(刘福龙, 江 涛, 左代姝, 等). Chinese Journal of Organic Chemistry(有机化学), 2002, 22(10): 761.
[2] LAN Qing, WU Li, WANG Xian-heng, et al(兰 青, 吴 丽, 王先恒，等). Chemical Research and Application(化学研究与应用), 2021, 33(5): 786.
[3] Prasad S B, Verma A K. Microscopy and Microanalysis, 2013, 19(6) : 1377.
[4] ZHANG Xue-bo, MA Hang-yu, SUN Teng-da, et al(张学博, 马航宇, 孙腾达, 等). Chinese Journal of Organic Chemistry(有机化学), 2019, 39(3): 2965.
[5] MENG Xiao-hui, HUANG Xu-bo, XIA Zhang-chen, et al(孟晓慧, 黄旭波, 夏张晨, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2025, 45(1): 107.
[6] ZHOU Su-zhen, XING Li, FAN Jin-bo, et al(周素珍, 邢 莉, 范金波, 等). Journal of Chinese Institute of Food Science and Technology(中国食品学报), 2023, 23(2): 61.
[7] Morris G M, Huey R, Lindstrom W, et al. Journal of Computational Chemistry, 2009, 30(16): 2785.
[8] Eberhardt J, Santos-Martins D, Tillack A F, et al. Journal of Chemical Information and Modeling, 2021, 61(8): 3891.
[9] ZENG Zao, LI Jin-hai, SHU Qun-wei, et al(曾 造, 李金海, 舒群威, 等). Chemistry Reagents(化学试剂), 2017, 39(11): 1155.
[10] SHI Meng-jie, LI Ze-meng, LU Yong-rui, et al(史梦洁, 李泽萌, 陆勇睿, 等). Chinese Journal of Analysis Laboratory(分析试验室), 2024, 43(3): 340.
[11] SHEN Bing-jun, LIU Ting-ting(申炳俊, 柳婷婷). Chinese Journal of Analytical Chemistry(分析化学), 2020, 48(10): 1383.
[12] WANG Ning, LIU Zhong-ying, HU Xiu-li, et al(王 宁, 刘忠英, 胡秀丽, 等). Chemical Journal of Chinese Universities(高等学校化学学报), 2011, 32(2): 241.
[13] Ross P D, Subramanian S. Biochemistry, 1981, 20(11): 3096.
[14] SUN Xiao-yue, BI Shu-yun, WU Jun, et al(孙晓悦, 毕淑云, 吴 鋆, 等). Journal of Molecular Science(分子科学学报), 2019, 35(2): 141.
[15] FENG Nan-nan, XIAN Man-kang, DING Xu-hui, et al(冯楠楠, 冼满康, 丁旭辉, 等). Journal of Instrumental Analysis(分析测试学报), 2024, 43(12): 1927.
[16] LU Dong-wei, WU Xiao-yu, XIE Xian, et al(逯东伟, 吴啸宇, 谢 宪, 等). Chinese Journal of Luminescence(发光学报), 2017, 38(3): 402.
[17] ZHANG Ai-qin, WANG Man, SHEN Gang-yi, et al(张爱芹, 王 嫚, 申刚义, 等). Chemical Journal of Chinese Universities(高等学校化学学报), 2020, 41(9): 2054.
[18] ZENG Zao, SHU Qun-wei, LI Jin-hai(曾 造, 舒群威, 李金海). Chemistry[化学通报(中英文)], 2018, 81(1): 83. |
| [1] |
CHEN Xing-wang, SSEKASAMBA Hakim, REN Kai-wen, LI Wei-xing, WANG Zi-yan, TANG Xiao-liang*, QIU Gao. Helium Atmospheric Pressure Dielectric Barrier Discharge Plasma Emission Spectroscopy Analysis and Voltage-Flow Co-Control Mechanism[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(10): 2754-2759. |
| [2] |
WANG Xiao-xia1, 2*, NIU Hao-ran1, SUN Ji-sheng1, WANG Ya-xiong1, 2, WANG Meng-han1, FU Rui1, 2, MAO Qing1, 2, ZHANG Jian-ling3, WANG Wei4. Study on the Interaction Between Lignite Fulvic Acid and Cellulase by Multispectral Method and Molecular Docking Simulation[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(08): 2190-2199. |
| [3] |
TAN Fang-ping1, LU Tong-suo1, 2*. Study of Near-Infrared Fingerprints of Ganoderma Lucidum in Different Growth Environments[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(07): 1968-1978. |
| [4] |
HU Zhi-jie1, LU Man-li2*, TIAN Ji-li1, ZHANG Wen-li2, WANG Mou-hua2. Rapid Measurement of Vitamin E in Vitamin E/Ultra-High Molecular Weight Polyethylene Powders by Infrared Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(07): 1900-1905. |
| [5] |
QU Wei1, 2*, LI Zi-shang1, 2*, LI Qian1, 2, ZHANG Hong-zhi1, 2. Study on the Coupling of Spectral Method With Sensitizer to Reduce the Detection Limit of Trace Indium in Copper Smelting Dust[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(05): 1319-1324. |
| [6] |
LIU Dan, YUAN Hui*, WAN Wei, XU Guang-tong. Application of Infrared Spectroscopy in Hydrogen Analysis of Hydrogen Fuel Cell Vehicles[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(04): 901-907. |
| [7] |
NI Zi-yue, LIU Ming-bo*, ZHENG Qi, HU Xue-qiang, YUE Yuan-bo, YANG Bo-zan, FAN Zhen, LI Cheng. Determination of Various Elements in Ceramic Materials by Wavelength Dispersive X-Ray Fluorescence Spectrometry With Fusion Sample
Preparation[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(03): 700-705. |
| [8] |
WANG Peng1, 2, MEN Qian-ni1, 2, GAN Li-ming1, 2, BAI Jin-feng4, WANG Xiao1, 2, JING Bin-qiang1, 2, KOU Shao-lei1, 2, LIU Hui-lan5, HE Tao1, 2*, LIU Jiu-fen3, 6*. Analysis Techniques and Optimization Models for the Determination of Au in Ores by Atomic Absorption Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(02): 426-433. |
| [9] |
MENG Xiao-hui1, 2, HUANG Xu-bo1, XIA Zhang-chen1, 2, XU Juan2, WANG Yan-bin1, CHENG Jun-wen1, YANG Liu1, HE Liang1*. Prohibition Mechanism Between Dihydromyricetin and Pancreatic Lipase by Multiple-Spectroscopy and Molecular Docking[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(01): 107-116. |
| [10] |
XIE Xing1, CHENG Xin-peng1, ZHANG Lu1*, LUO Jing1, WANG Le-huai1, LIN Wen-jing1, LU Fei-yan1, TU Zong-cai1, 2*. Study on the Interaction Mechanism of Ellagic Acid and Urolisine A~D With HSA Based on Spectral Analysis[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2025, 45(01): 282-290. |
| [11] |
LIAO Xue-liang, LIU Ming-bo, CHENG Da-wei, SHEN Xue-jing. Analysis and Calculation of Escape Peaks in Silicon Drift Detectors[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(05): 1297-1300. |
| [12] |
CHENG Wen-xuan1, ZHANG Qing-xian1*, LIU Yu1, ZOU Li-kou2*. Study on Detection of Antibiotic Residues in Eggs by Laser-Induced
Fluorescence[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(05): 1245-1254. |
| [13] |
GE Qing, LIU Jin*, HAN Tong-shuai, LIU Wen-bo, LIU Rong, XU Ke-xin. Influence of Medium's Optical Properties on Glucose Detection
Sensitivity in Tissue Phantoms[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(05): 1262-1268. |
| [14] |
ZHANG Chen-ling, HAN Mei*, LIU Jia, JIA Na, LIU Bing-bing, ZHANG Yong-tao. Determination of Mineral Elements and Dissolution Characteristics in
Lycium Ruthenicum Murray[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(05): 1307-1311. |
| [15] |
XU Rong1, AO Dong-mei2*, XU Xin1, 2, WANG Zhan-lin1, 2, HU Ying2, LIU Sai1, QIAO Hai-li1, XU Chang-qing1*. Study on the Identification Method of Lycium Barbarum Cultivars in Ningxia Based on Infrared Spectrum and Cluster Analysis[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(05): 1386-1391. |
|
|
|
|
