脱氢姜酮、查耳酮和异丁香酚类似物作为体外抗癌剂。
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.
作者信息
Tatsuzaki Jin, Bastow Kenneth F, Nakagawa-Goto Kyoko, Nakamura Seiko, Itokawa Hideji, Lee Kuo-Hsiung
机构信息
Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, USA.
出版信息
J Nat Prod. 2006 Oct;69(10):1445-9. doi: 10.1021/np060252z.
Abstract
Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 microg/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 microg/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 microg/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.
摘要
合成了28种与脱氢姜酮（1）、异丁香酚（3）和2-羟基查耳酮（4）相关的化合物，并对其进行体外抗人肿瘤细胞复制活性评估。除异丁香酚类似物27 - 35外，大多数化合物对KB、KB - VCR（一种多药耐药衍生物）和A549细胞系表现出中度或强细胞毒性活性。特别是，查耳酮15对A549细胞系表现出显著的细胞毒性活性，IC50值为0.6μg/mL。此外，脱氢姜酮类似物11以及查耳酮16和17对KB（IC50值分别为2.0、1.0和2.0μg/mL）和KB - VCR（IC50值分别为1.9、1.0和2.0μg/mL）细胞均表现出显著且相似的细胞毒性活性，表明它们不是P - 糖蛋白药物外排泵的底物。
相似文献
1
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.脱氢姜酮、查耳酮和异丁香酚类似物作为体外抗癌剂。
J Nat Prod. 2006 Oct;69(10):1445-9. doi: 10.1021/np060252z.
2
Molecular Docking Study, Cytotoxicity, Cell Cycle Arrest and Apoptotic Induction of Novel Chalcones Incorporating Thiadiazolyl Isoquinoline in Cervical Cancer.新型查尔酮类硫代二唑并异喹啉衍生物的分子对接研究及其对宫颈癌的细胞毒性、细胞周期阻滞和凋亡诱导作用。
Anticancer Agents Med Chem. 2020;20(1):70-83. doi: 10.2174/1871520619666191024121116.
3
Synthesis and evaluation of novel α-substituted chalcones with potent anti-cancer activities and ability to overcome multidrug resistance.新型α-取代查耳酮的合成与评价及其具有的强大抗癌活性和克服多药耐药性的能力。
Bioorg Chem. 2019 Jun;87:123-135. doi: 10.1016/j.bioorg.2019.03.014. Epub 2019 Mar 7.
4
Synthesis and biological evaluation of indolyl chalcones as antitumor agents.吲哚查耳酮类化合物的合成及抗肿瘤活性评价。
Bioorg Med Chem Lett. 2010 Jul 1;20(13):3916-9. doi: 10.1016/j.bmcl.2010.05.016. Epub 2010 May 13.
5
Synthesis of novel β-carboline based chalcones with high cytotoxic activity against breast cancer cells.具有高抗乳腺癌细胞细胞毒性活性的新型β-咔啉基查耳酮的合成。
Bioorg Med Chem Lett. 2014 Jul 1;24(13):2820-4. doi: 10.1016/j.bmcl.2014.04.109. Epub 2014 May 4.
6
Discovery of a new dihydroeugenol-chalcone hybrid with cytotoxic and anti-migratory potential: A dual-action hit for cancer therapeutics.发现一种具有细胞毒性和抗迁移潜力的新型二氢丁香酚-查耳酮杂合物：癌症治疗的双重作用先导化合物。
Bioorg Med Chem. 2023 Dec 15;96:117516. doi: 10.1016/j.bmc.2023.117516. Epub 2023 Nov 3.
7
Discovery of thiazole-based-chalcones and 4-hetarylthiazoles as potent anticancer agents: Synthesis, docking study and anticancer activity.噻唑基查耳酮和 4-杂芳基噻唑类化合物的发现：合成、对接研究及抗癌活性。
Bioorg Chem. 2020 May;98:103761. doi: 10.1016/j.bioorg.2020.103761. Epub 2020 Mar 14.
8
Heterocyclic chalcone analogues as potential anticancer agents.杂环查尔酮类似物作为潜在的抗癌剂。
Anticancer Agents Med Chem. 2013 Mar;13(3):422-32.
9
Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers.脱氢姜酮和异丁香酚作为脂质过氧化抑制剂和自由基清除剂。
Biochem Pharmacol. 1993 Dec 3;46(11):2067-72. doi: 10.1016/0006-2952(93)90649-h.
10
Antitumor agents. 280. Multidrug resistance-selective desmosdumotin B analogues.抗肿瘤药。280. 多药耐药性选择性地丝菌素 B 类似物。
J Med Chem. 2010 Sep 23;53(18):6699-705. doi: 10.1021/jm100846r.
引用本文的文献
1
Anticarcinogenic Potency of EF24: An Overview of Its Pharmacokinetics, Efficacy, Mechanism of Action, and Nanoformulation for Drug Delivery.EF24的抗癌效力：其药代动力学、疗效、作用机制及药物递送纳米制剂概述
Cancers (Basel). 2023 Nov 20;15(22):5478. doi: 10.3390/cancers15225478.
2
Natural and natural-like polyphenol compounds: antioxidant activity and potential for therapeutic application.天然及类天然多酚化合物：抗氧化活性及治疗应用潜力
Arch Med Sci. 2021 Apr 18;19(3):651-671. doi: 10.5114/aoms/135379. eCollection 2023.
3
Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry.查尔酮：药物化学中一种有前景的生物活性骨架。
Pharmaceuticals (Basel). 2022 Oct 11;15(10):1250. doi: 10.3390/ph15101250.
4
Chemoselective and metal-free reduction of α,β-unsaturated ketones by produced benzeneselenol from -(-butyl) Se-phenyl selenocarbonate.由-(-丁基)硒代苯基碳酸硒酯生成的苯硒酚对α,β-不饱和酮进行化学选择性和无金属还原。
RSC Adv. 2020 Sep 11;10(56):33706-33717. doi: 10.1039/d0ra07128e. eCollection 2020 Sep 10.
5
var. : Red Ginger's Medicinal Uses.变种：红姜的药用用途。
Molecules. 2022 Jan 25;27(3):775. doi: 10.3390/molecules27030775.
6
Synthesis and Biological Evaluation of Hydroxylated Monocarbonyl Curcumin Derivatives as Potential Inducers of Neprilysin Activity.作为中性内肽酶活性潜在诱导剂的羟基化单羰基姜黄素衍生物的合成与生物学评价
Biomedicines. 2021 Aug 3;9(8):955. doi: 10.3390/biomedicines9080955.
7
Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.（杂）芳基 2-(2-羟基芳基)环丙基酮的合成。
Molecules. 2020 Dec 5;25(23):5748. doi: 10.3390/molecules25235748.
8
Dehydrozingerone, a Curcumin Analog, as a Potential Anti-Prostate Cancer Inhibitor In Vitro and In Vivo.去氢姜酮，姜黄素类似物，在体外和体内作为一种潜在的抗前列腺癌抑制剂。
Molecules. 2020 Jun 12;25(12):2737. doi: 10.3390/molecules25122737.
9
Privileged Scaffold Chalcone: Synthesis, Characterization and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic and Chemoinformatics Approaches.特权支架查尔酮：采用光谱学和化学信息学方法的合成、表征及其与牛血清白蛋白的作用机制研究
ACS Omega. 2020 Jan 27;5(5):2267-2279. doi: 10.1021/acsomega.9b03479. eCollection 2020 Feb 11.
10
Electronic Effects of Substituents on -M(bpy-R)(CO) (M = Mn, Re) Complexes for Homogeneous CO Electroreduction.取代基对用于均相CO电还原的-M(bpy-R)(CO)（M = Mn，Re）配合物的电子效应
Front Chem. 2019 Jun 5;7:417. doi: 10.3389/fchem.2019.00417. eCollection 2019.
本文引用的文献
1
Prenylated benzophenones and xanthones from Hypericum scabrum.糙叶金丝桃中的异戊烯基化二苯甲酮和呫吨酮
J Nat Prod. 2004 Nov;67(11):1870-5. doi: 10.1021/np040024+.
2
Cancer chemopreventive activity of phenylpropanoids and phytoquinoids from Illicium plants.八角属植物中苯丙素类化合物和植物醌类化合物的癌症化学预防活性。
Cancer Lett. 2004 Oct 28;214(2):165-9. doi: 10.1016/j.canlet.2004.05.005.
3
New bioactive prenylflavonoids and dibenzocycloheptene derivative from roots of Dendrolobium lanceolatum.来自披针叶猴耳环根的新型生物活性异戊烯基黄酮和二苯并环庚烯衍生物。
J Nat Prod. 2004 Jun;67(6):968-72. doi: 10.1021/np030519j.
4
Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents.新型姜黄素类似物作为抗癌和抗血管生成剂的合成及生物学评价
Bioorg Med Chem. 2004 Jul 15;12(14):3871-83. doi: 10.1016/j.bmc.2004.05.006.
5
Antitumor agents 222. Synthesis and anti-androgen activity of new diarylheptanoids.抗肿瘤药物222.新型二芳基庚烷类化合物的合成及抗雄激素活性
Bioorg Med Chem. 2003 Nov 17;11(23):5083-90. doi: 10.1016/j.bmc.2003.08.029.
6
Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents.抗肿瘤剂。217. 姜黄素类似物作为新型雄激素受体拮抗剂及潜在的抗前列腺癌药物。
J Med Chem. 2002 Nov 7;45(23):5037-42. doi: 10.1021/jm020200g.
7
Antitumor agents. Part 214: synthesis and evaluation of curcumin analogues as cytotoxic agents.抗肿瘤剂。第214部分：姜黄素类似物作为细胞毒性剂的合成与评价
Bioorg Med Chem. 2002 Nov;10(11):3481-7. doi: 10.1016/s0968-0896(02)00249-3.
8
Cytotoxic isoflavones from Erythrina indica.刺桐中的细胞毒性异黄酮。
Phytochemistry. 2001 Dec;58(7):1113-20. doi: 10.1016/s0031-9422(01)00368-5.
9
A facile synthetic approach to prenylated flavanones: first total syntheses of (+/-)-bonannione A and (+/-)-sophoraflavanone A.一种简便的合成异戊烯基黄酮的方法：（±）-波那酮A和（±）-槐黄酮A的首次全合成。
J Nat Prod. 2001 Feb;64(2):196-9. doi: 10.1021/np0001124.
10
Mappain, a new cytotoxic prenylated stilbene from Macaranga mappa.麻疯树素，一种从红背桂中提取的新型具有细胞毒性的异戊烯基化芪类化合物。
J Nat Prod. 2001 Jan;64(1):103-5. doi: 10.1021/np000265r.
Zotero 插件