苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究

doi:10.6023/cjoc202209040

有机化学 ›› 2023, Vol. 43 ›› Issue (6): 2126-2135.DOI: 10.6023/cjoc202209040 上一篇下一篇

研究论文

苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究

庞盼杏^a, 宁蓉^a, 祝创^a, 黄文洁^a, 马献力^a, 蒋彩娜^a, 李芳耀^a^,^*(), 周小群^b^,^*()

a 桂林医学院药学院广西桂林 541004
b 桂林医学院人文与管理学院广西桂林 541004

收稿日期:2022-09-30 修回日期:2022-12-11 发布日期:2023-01-11
作者简介:
^†共同第一作者
基金资助:
国家级大学生创新创业训练计划(202010601021); 广西高校中青年科研基础能力提升(2019KY051); 广西自然科学基金(2018GXNSFAA281200); 桂林市科学研究与技术开发计划(20210227-1)

Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives

Panxing Pang^a, Rong Ning^a, Chuang Zhu^a, Wenjie Huang^a, Xianli Ma^a, Caina Jiang^a, Fangyao Li^a,*(), Xiaoqun Zhou^b,*()

a School of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004
b College of Humanities and Management, Guilin Medical University, Guilin, Guangxi 541004

Received:2022-09-30 Revised:2022-12-11 Published:2023-01-11
Contact: * E-mail: lifangyao2006@163.com;zhouxqgy@163.com
About author:
^†These authors contributed equally to this work
Supported by:
National Innovation and Entrepreneurship Training Program for College Students(202010601021); Guangxi Young and Middle-Aged Scientific Research Basic Ability Improvement Project for Colleges and Universities(2019KY051); Natural Science Foundation of Guangxi Province(2018GXNSFAA281200); Project for Science Research and Technology Development of Guilin City(20210227-1)

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摘要/Abstract

为了寻找高效低毒的新型抗肿瘤化合物, 设计并合成了一系列新型的苦参碱缩氨基脲类化合物. 采用噻唑蓝(MTT)法测定目标化合物对人肺癌细胞(A549)、人肝癌细胞(HepG2)、人宫颈癌细胞(Hela)、人胃癌细胞(MGC803)细胞株及人正常肝细胞株(L-O2)的细胞毒活性. 结果表明, 大多数衍生物对肿瘤细胞的细胞毒性明显高于母体化合物. 其中14-甲酰基-15-氯-苦参碱缩N-(3-氯苯基)氨基脲(6c)和14-甲酰基-15-氯-苦参碱缩N-(3-硝基苯基)氨基脲(6f)对人肺癌A549细胞株表现出良好的抑制活性, IC₅₀值分别为(11.70±0.25)和(15.61±0.07) μmol/L, 活性优于阳性对照药喜树碱. 同时, 对人胃癌MGC803细胞株IC₅₀值分别为(11.32±1.07)和(9.27±2.03) μmol/L, 并且对人正常肝细胞株(L-O2)表现出较低的细胞毒性. 流式细胞术及线粒体膜电位检测表明, 化合物6f能够剂量依赖性地诱导MGC803细胞凋亡, 并降低线粒体膜电位. 上述研究为苦参碱的结构修饰提供了思路.

关键词: 苦参碱, 缩氨基脲, 合成, 体外抗肿瘤活性

In order to search for novel antitumor drugs with high efficiency and low toxicity, matrine semicarbazide derivatives were designed and synthesized. The antiproliferative activities of target compounds in four human cancer cell lines of A549 (lung), HepG2 (liver), Hela (epithelial cervical), MGC-803 (gastric) and a human normal cell of L-O2 (liver) were evaluated by methyl thiazolyl tetrazolium (MTT) assay. Biological screening results demonstrated that most of the derivatives exhibited more potent cytotoxicity against tumor cell lines superior to parent compound matrine. Among them, compounds of 14-formyl-15-chloro-matrine N-(3-chlorophenyl) semicarbazide (6c) and 14-formyl-15-chloro-matrine N-(3-nitrophenyl) semicarbazide (6f) displayed better antiproliferative activity with IC₅₀ values of (11.70±0.25) and (15.61±0.07) μmol/L toward A549 cells compared with camptothecin, and with IC₅₀ values of (11.32±1.07) and (9.27±2.03) μmol/L against MGC-803 cells. Moreover, they exhibited lower cytotoxicity against human normal liver cell line L-O2. Flow cytometry and JC-1 mitochondrial membrane potential detection showed that compound 6f could induce apoptosis of MGC803 cells and reduce the mitochondrial membrane potential. It would provide a new idea for the structural modification of matrine.

Key words: matrine, semicarbazide, synthesis, in vitro antitumor activity

引用此文

庞盼杏, 宁蓉, 祝创, 黄文洁, 马献力, 蒋彩娜, 李芳耀, 周小群. 苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究[J]. 有机化学, 2023, 43(6): 2126-2135.

Panxing Pang, Rong Ning, Chuang Zhu, Wenjie Huang, Xianli Ma, Caina Jiang, Fangyao Li, Xiaoqun Zhou. Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2126-2135.

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图/表 9

图1. 具有抗肿瘤活性的缩氨基脲化合物

Figure 1. Semicarbazone derivatives with antitumor activity

图2. 苦参碱与具有抗肿瘤活性的苦参碱衍生物

Figure 2. Matrine and matrine derivatives with antitumor activity

图式1. 化合物6a~6o的合成

Scheme 1. Synthesis of compounds 6a~6o Reagents and conditions: (a) (1) CH2Cl2, DMF, POCl3, 0 ℃, 1 h; (2) mix, r.t., 8 h; (3) hydrolysis, 60 ℃, 2 h, pH 8~9. (b) Phenyl chloroformate, anhydrous acetone, dehydrated molecular sieve, 0~5 ℃, 5.5 h. (c) Dioxane, NH2NH2?H2O (ω=80%), 102 ℃, 6 h; (d) ethanol, reflux12 h, 80 ℃.

Complex	6a
Empirical formula	C₂₃H₂₈ClN₅O
Formula weight (M_r)	425.95
Crystal system	Orthorhombic
Space group	P2₁2₁2₁
a/nm	0.52876(1)
b/nm	1.53224(3)
c/nm	2.68038(5)
V/nm³	2.17161(7)
Z	4
F(000)	904
D_x/(Mg•m^–3)	1.303
Cu Kα radiation (λ)/nm	0.154184
μ/mm^–1	1.75
T/K	293
Measured reflections	16468
Independent reflections	4367
Reflections with I>2(I)	3707
R_int	0.052

表1. 6a的晶体结构数据

Table 1. Crystal data and structure refinement for 6a

图3. 化合物6a的晶体结构图

Figure 3. Crystal structure of 6a

Compd.	R	IC₅₀^a/(μmol•L^–1)
Compd.	R	L-O2	MGC803	HeLa	A549	Hepg2
6a	H	30.46±0.12	17.41±1.52	24.86±0.70	46.53±0.40	83.93±1.30
6b	2-Cl	76.50±2.82	11.66±1.31	17.30±2.04	25.48±2.72	>100
6c	3-Cl	27.45±2 47	11.32±1.07	16.94±1.97	11.70±0.25	35.82±1.93
6d	4-Cl	12.77±1.87	14.36±2.99	15.47±1.24	45.48±1.11	46.75±1.59
6e	2-NO₂	31.46±0.98	17.47±2.58	32.51±0.14	33.31±0.03	>100
6f	3-NO₂	63.99±2.71	9.27±2.03	50.84±0.91	15.61±0.07	27.59±2.02
6g	4-NO₂	33.24±0.74	21.70±1.89	30.21±1.71	63.74±1.21	>100
6h	2-Br	45.85±1.47	23.63±0.22	38.34±0.65	71.39±4.84	59.82±2.85
6i	4-Br	12.36±2.64	13.73±1.57	16.34±1.87	20.72±0.49	>100
6j	2-F	32.90±0.36	14.16±2.35	30.09±2.69	49.90±1.70	>100
6k	3-F	26.70±1.64	16.46±1.99	23.50±2.8	62.73±2.42	38.64±4.47
6l	4-F	11.94±1.85	17.28±1.27	15.94±1.41	41.49±1.46	31.40±2.31
6m	2-CH₃	27.49±2.22	20.84±0.11	21.34±2.36	56.86±1.57	56.90±2.43
6n	3-CH₃	33.48±2.23	19.73±1.04	25.35±0.19	45.11±1.32	53.94±2.67
6o	4-CH₃	18.02±2.13	13.81±0.23	21.21±0.60	53.44±2.18	92.76±3.05
苦参碱		>100	>100	>100	>100	>100
喜树碱^b		4.44±2.54	8.13±2.13	2.00±0.8	20.34±1.53	2.30±1.19

表2. 目标化合物对四种肿瘤细胞系及正常细胞的体外抗增殖活性

Table 2. Antiproliferative activity in four tumor and one normal cell lines of target compounds

图4. 化合物6f对MGC-803细胞凋亡的影响

Figure 4. Effects of 6f on apoptosis of gastric cancer MGC-803 cells (A) Apoptosis rate of MGC-803 cells was determined by flow cytometry with Annexin V/PI staining. MGC-803 cells were incubated with 10, 15, and 20 μmol/L 6f for 48 h. (B) Quantitative analysis of apoptotic cells in A. *p<0.05, **p<0.01, ***p<0.001 compared with the control group.

图5. 胃癌MGC-803细胞在化合物6f作用下的形态学变化

Figure 5. Morphological changes of gastric cancer MGC-803 cells treated with compound 6f

图6. 化合物6f对胃癌细胞MGC-803线粒体膜电位的影响

Figure 6. Effects of 6f on mitochondrial membrane potential (MMP) of gastric cancer MGC-803 cells (A) Representative pictures of mitochondrial membrane potential of MGC-803 cells treated with 6f for 48 h. (B) Quantitative analysis of A. *p<0.05, **p<0.01, ***p<0.001 compared with the control group.

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苦参碱缩氨基脲类化合物的合成及其体外抗肿瘤活性研究

Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives

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