Synthesis，anti-melanoma activity and acute toxicity of aporphine alkaloids in zebrafish

WAN Yili; ZHONG Hui; CHEN Li; SUN Jianbo

doi:10.11665/j.issn.1000-5048.20210503

Journal of China Pharmaceutical University > 2021 > 52(5): 529-535. > DOI: 10.11665/j.issn.1000-5048.20210503

WAN Yili, ZHONG Hui, CHEN Li, SUN Jianbo. Synthesis，anti-melanoma activity and acute toxicity of aporphine alkaloids in zebrafish[J]. Journal of China Pharmaceutical University, 2021, 52(5): 529-535. DOI: 10.11665/j.issn.1000-5048.20210503

Citation:

PDF (6925 KB)

Synthesis，anti-melanoma activity and acute toxicity of aporphine alkaloids in zebrafish

School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, China

Funds: This study was supported by the National Natural Science Foundation of China (No.31870325, No.31500277)

More Information

Received Date: March 28, 2021
Revised Date: September 13, 2021

Graphical Abstract

Abstract

Abstract

In this study, 10 aporphine alkaloids were synthesized with 1, 2-methylenedioxy substituent in ring A and 9, 10, 11-position with different substituents in ring D. Their structures were determined by ESI-MS,¹³C NMR and ¹H NMR.The potencial antitumor activity of these compounds against B16F10 melanoma cells were evaluated by MTT assay, and their structure-activity relationship was further analyzed.Meanwhile, zebrafish acute toxicity test was conducted to evaluate the safety of the active compounds.The results showed that some compounds had strong inhibitory activity on tumor cells, and could significantly inhibit the proliferation of B16F10 melanoma cells.Compound IVa has the best anti-melanoma activity with wide safety range, and can be used as a lead compound for further study on anti-proliferation of B16F10 melanoma cells.
- aporphine alkaloids,
- synthesis,
- melanoma,
- safety evaluation,
- structure activity relationship

FullText(HTML)

References (13)

References

[1]	. Chin Tradit Herb Drugs（中草药），2018，49（3）：712-724.
[2]	Lin XW，Wang RQ，Tan YF，et al. Advances on pharmacokinetic researches on aporphine alkaloids［J］. Prog Pharm Sci（药学进展），2020，44（6）：451-458.
[3]	Liu X，Sun Y，Dou LM，et al. Research progress in anti-diabetic activities of aporphine alkaloids［J］. Prog Pharm Sci（药学进展），2017，41（9）：704-709.
[4]	Zhao QZ，Zhao YM. Progress in biologlcal activities of aporphinoid alkaloids［J］. Nat Prod Res Dev（天然产物研究与开发），2006，18（2）：316-324.
[5]	Zhang A，Zhang Y，Branfman AR，et al. Advances in development of dopaminergic aporphinoids［J］. J Med Chem，2007，50（2）：171-181.
[6]	Liu YJ，Liu JX，Di DL. Progress on anticancer activity of aporphine alkaloids［J］. Chin Tradit Herb Drugs（中草药），2012，43（4）：806-814.
[7]	Wang B，Zhao YJ，Zhao YL，et al. Exploring aporphine as anti-inflammatory and analgesic lead from Dactylicapnos scandens［J］. Org Lett，2020，22（1）：257-260.
[8]	Wang R，Zhou J，Shi G，et al. Aporphine and phenanthrene alkaloids with antioxidant activity from the roots of Stephania tetrandra［J］. Fitoterapia，2020，143：104551.
[9]	Tran TD，Pham NB，Fechner G，et al. Chemical investigation of drug-like compounds from the Australian tree，Neolitseadealbata［J］. Bioorg Med Chem Lett，2010，20（19）：5859-5863.
[10]	Jin Q，Yang D，Dai Z，et al. Antitumor aporphine alkaloids from Thalictrum wangii［J］. Fitoterapia，2018，128：204-212.
[11]	Bai Z，Shang FY，Dai WG，et al. Synthesis and antitumor activities of NO-donating rhein derivatives［J］. J China Pharm Univ（中国药科大学学报），2021，52（1）：38-43.
[12]	Liu L，Pei S，Wu H，et al. Drug screening model of treating pigmentation disorders in tyrpla transgenic zebrafish［J］. J China Pharm Univ（中国药科大学学报），2016，47（6）：740-743.
[13]	Dai MZ，Huang YF，Peng Y，et al. Advances in zebrafish experimental research on developmental toxicity and teratogenicity［J］. Acta Lab Animalis Sci Sin（中国实验动物学报），2020，28（1）：137-142.

[1]	ZHANG Xueling, LI Na, CHEN Li. Progress of research on celastrol derivatives as anti-tumor agents[J]. Journal of China Pharmaceutical University, 2024, 55(6): 826-836. DOI: 10.11665/j.issn.1000-5048.2023041802
[2]	ZHANG Wanyue, LIU Wei, XU Hang, GAO Xiangdong. Advanced structure analysis and structure-activity relationship of polysaccharide SGP-2 from Sarcandra glabra[J]. Journal of China Pharmaceutical University, 2021, 52(5): 630-635. DOI: 10.11665/j.issn.1000-5048.20210517
[3]	LIU Haomiao, HU Xiaowen, ZHOU Jinpei, ZHANG Huibin. Advances of G protein coupled receptor 119 agonists and their structure-activity relationship[J]. Journal of China Pharmaceutical University, 2013, 44(1): 11-19. DOI: 10.11665/j.issn.1000-5048.20130102
[4]	ZHENG Kai-bo, SUN Cheng-bin, MAO Hai-li, YANG Zai-bo. Progress in the research of chemical structural modification of ursolic acid and structure-activity relationship[J]. Journal of China Pharmaceutical University, 2009, 40(6): 580-584.
[5]	Progress of the Classification of β-lactamases and Its Relationship Between Structure and Function[J]. Journal of China Pharmaceutical University, 2003, (4): 90-94.
[6]	Structure-Cytotoxic Activity Relationships of Diterpenoid Tanshinones from Salvias[J]. Journal of China Pharmaceutical University, 2002, (1): 8-14.
[7]	Synthesis, Analgesic Activity and Structure-Activity Relationship of 4-N-Cyclohexyl Analogs of Some Fentanyl Derivatives[J]. Journal of China Pharmaceutical University, 1993, (3): 139-144.
[8]	Structural-Activity Relations Study on the Derivatives of 3,4-Dimethoxyphenylenediamine[J]. Journal of China Pharmaceutical University, 1992, (4): 217-220.
[9]	DETERMINATION OF HYDROLYSIS RATE AND PRELIMINARY STRUCTURE-ACTIVITY RELATIONSHIP OF THIOHYDANTOIN DERIVATIVES[J]. Journal of China Pharmaceutical University, 1989, (4): 199-202.
[10]	RELATIONSHIP BETWEEN STRUCTURE AND ANTIBACTERIAL ACTIVITIES OF TANSHINONES AND RELATED COMPOUNDS[J]. Journal of China Pharmaceutical University, 1988, (4): 258-262.

Cited By

Cited by

Periodical cited type(1)

苏琦，张珂，黄淑琪，朱希强，刘晓鹏，姜宁. 逆境胁迫对药用植物药效成分积累的影响. 湖北民族大学学报(自然科学版). 2022(02): 129-134+180 .

Other cited types(0)

Get Citation

PDF

XML

Article views (240) PDF downloads (558) Cited by(1)

Turn off MathJax

Article Contents

Abstract

References

Synthesis，anti-melanoma activity and acute toxicity of aporphine alkaloids in zebrafish

Abstract

References

Related Articles

Cited by

Periodical cited type(1)

Other cited types(0)

Catalog

Synthesis，anti-melanoma activity and acute toxicity of aporphine alkaloids in zebrafish

Abstract

References

Related Articles

Cited by

Periodical cited type(1)

Other cited types(0)

Catalog

Export File

Citation

Format

Content