Structural simplification of evodiamine: Discovery of novel tetrahydro-β-carboline derivatives as potent antitumor agents

Ma, Zonglin; Huang, Ya‐Hui; Wan, Kun; Zhu, Fugui; Sheng, Chunquan; Chen, Shuqiang; Liu, Dan; Dong, Guoqiang

doi:10.1016/j.bmcl.2021.127954

Cited by 6 publications

(2 citation statements)

References 27 publications

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“…Evodiamine, an indolequinone alkaloid derived from Chinese herbal medicine Evodia rutaecarpa , represents a promising antitumor lead compound. − Previously, a number of evodiamine derivatives were designed, − and we identified 3-fluoro-10-hydroxylevodiamine (compound 2 in Figure B) with excellent in vitro antitumor activity . However, compound 2 possesses poor water solubility and limited in vivo antitumor activity, which has hampered further development in clinical treatment.…”

Section: Introductionmentioning

confidence: 97%

Design of Evodiamine–Glucose Conjugates with Improved In Vivo Antitumor Activity

Wu,

Chen,

Chen

et al. 2024

J. Med. Chem.

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Natural product evodiamine is a multitargeting antitumor lead compound. However, clinical development of evodiamine derivatives was hampered by poor water solubility and limited in vivo antitumor potency. Herein, a series of evodiamine−glucose conjugates were designed by additional targeting glucose transporter-1 (GLUT1). Compared with the lead compound, conjugate 8 exhibited obvious enhancement in water solubility and in vivo antitumor efficacy. Furthermore, the effect of GLUT1 targeting also led to lower cytotoxicity to normal cells. Antitumor mechanism studies manifested that conjugate 8 acted by Top1/Top2 dual inhibition, apoptosis induction, and G 2 /M cell cycle arrest, which selectively targeted tumor cells with a high expression level of GLUT1. Thus, evodiamine−glucose conjugates showed promising features as potential antitumor agents.

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Section: Introductionmentioning

confidence: 97%

Design of Evodiamine–Glucose Conjugates with Improved In Vivo Antitumor Activity

Wu,

Chen,

Chen

et al. 2024

J. Med. Chem.

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“…[2] β-Carboline scaffold is distributed widely in nature. Examples include seeds [3] and fruits [4] of Peganum harmala L, roots of Psammosilene tunicoides, [5] Evodiae fructus herb, [6] Picrasma quassioides, [7] Vochysia divergens, [8] marine sponge Hyritos reticulatus, [9] marine tunicate Cnemidocarpa stolonifera, [10] and marine bryozoan Pterocella vesiculosa. [11] Owing to their important biological activities, [12] many of these alkaloids were also prepared synthetically.…”

Section: Introductionmentioning

confidence: 99%

The Progress in Pictet‐Spengler β‐Carboline Synthesis under Green Conditions

Mousa,

Adly,

Mahmoud

et al. 2024

ChemistrySelect

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Abstractβ‐Carboline ring is widely distributed in nature and several β‐carboline alkaloids were extracted from marine creatures, bacteria, fungi, food stuffs, plants, and mammals. Synthetic β‐carbolines derivatives were reported to exhibit various biological activities. This review highlighted the recent progress achieved in the last decade in the Pictet‐Spengler synthesis of β‐carboline derivatives with a special focus on the green methods and green catalysts used for the synthesis.

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Strategy to Construct Polycyclic Scaffolds via Formal Aza‐Diels‐Alder Reaction of Dihydro‐β‐Carboline with Heterodiene Precursor

et al. 2023

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Structural simplification of evodiamine: Discovery of novel tetrahydro-β-carboline derivatives as potent antitumor agents

Cited by 6 publications

References 27 publications

Design of Evodiamine–Glucose Conjugates with Improved In Vivo Antitumor Activity

Design of Evodiamine–Glucose Conjugates with Improved In Vivo Antitumor Activity

The Progress in Pictet‐Spengler β‐Carboline Synthesis under Green Conditions

Strategy to Construct Polycyclic Scaffolds via Formal Aza‐Diels‐Alder Reaction of Dihydro‐β‐Carboline with Heterodiene Precursor

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