设计,合成和生物活动评估含有异环的β-碳醇衍生物
Guiyun Wu1, Wenhang Wang1, Fulian Li1
1Guizhou Engineering Laboratory for Synthetic Drugs, College of Pharmacy, Guizhou University, Guiyang 550025, China.
Molecules (Basel, Switzerland)
|November 9, 2024
概括
一种新的β-卡博林衍生物,化合物8q,显示出对前列腺癌细胞 (PC-3) 的显著抗瘤潜力. 它通过诱导亡和反应性氧物种 (ROS) 积累,有效地抑制了增殖和迁移.
科学领域:
- 药用化学 医学化学
- 有机合成 有机合成
- 癌症生物学 癌症生物学
背景情况:
- 新型抗癌药物的开发对于有效的癌症治疗至关重要.
- β-卡博林衍生物代表着具有多样化的生物活性的一类有前途的化合物.
- 向前列腺癌,特别是耐药细胞系,仍然是一个重大的临床挑战.
研究的目的:
- 设计和合成具有潜在抗瘤活性的新型β-卡博林衍生物.
- 为了评估合成化合物的疗效与人类癌症细胞系的小组对比.
- 为了研究最强效的化合物在前列腺癌细胞中的作用机制.
主要方法:
- 合成含有异环的β-卡博林衍生物.
- 使用MTT测定对A549,K562,PC-3和T47D细胞系进行抗瘤活性查.
- 细胞增殖,迁移测定,亡分析,反应性氧物种 (ROS) 检测和PC-3细胞中化合物8q的细胞周期分析.
主要成果:
- 一系列β-卡博林衍生物成功合成和表征.
- 化合物8q对PC-3细胞具有显著的抑制活性,IC50为9.86μM.
- 化合物8q抑制了PC-3细胞的增殖和迁移,诱导了细胞亡,增加了ROS水平,并导致G0/G1细胞周期停止.
结论:
- 化合物8q是前列腺癌细胞生长和迁移的强有力的抑制剂.
- 化合物8q的抗瘤活性是通过亡诱导和ROS生成进行的.
- 这项研究强调了β-卡博林衍生物作为抗癌剂的治疗潜力,特别是对于前列腺癌.
相关概念视频
01:28Structures of Carboxylic Acid Derivatives
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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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01:26Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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01:202° Amines to N-Nitrosamines: Reaction with NaNO2
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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01:10Nomenclature of Aryl and Heterocyclic Amines
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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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