Berberine derivatives with a long alkyl chain branched by hydroxyl group and methoxycarbonyl group at 9-position show improved anti-proliferation activity and membrane permeability in A549 cells

Liu, Yi; Zhu, Kexin; Cao, Lei; Xie, Zhifu; Gu, Min; Lü, Wei; Li, Jingya; Nan, Fangfang

doi:10.1038/s41401-019-0346-1

Cited by 14 publications

(13 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, the assessment of berberine derivatives with cis-substituents at positions C9 and C13 [ 117 , 118 ] or 13-[CH2CO-Cys-(Bzl)-OBzl]-berberine [ 119 ] and a series of berberine derivatives with modified position 9-O [ 120 , 121 ] was described. The methylene-dioxy and methoxyl groups in berberine seem to be especially important for the anticancer activity exhibited by its derivatives [ 122 ].…”

Section: Challenge To New Derivatives and Formulations Of Berberinmentioning

confidence: 99%

Biological Activity of Berberine—A Summary Update

Och

Podgórski

Nowak

2020

Toxins

121

View full text Add to dashboard Cite

Berberine is a plant metabolite belonging to the group of isoquinoline alkaloids with strong biological and pharmacological activity. Currently, berberine is receiving considerable interest due to its anticancer activity based on many biochemical pathways, especially its proapoptotic and anti-inflammatory activity. Therefore, the growing number of papers on berberine demands summarizing the knowledge and research trends. The efficacy of berberine in breast and colon cancers seems to be the most promising aspect. Many papers focus on novel therapeutic strategies based on new formulations or search for new active derivatives. The activity of berberine is very important as regards sensitization and support of anticancer therapy in combination with well-known but in some cases inefficient therapeutics. Currently, the compound is being assessed in many important clinical trials and is one of the most promising and intensively examined natural agents.

show abstract

Section: Challenge To New Derivatives and Formulations Of Berberinmentioning

confidence: 99%

Biological Activity of Berberine—A Summary Update

Och

Podgórski

Nowak

2020

Toxins

121

View full text Add to dashboard Cite

show abstract

“…Esters, amides, and sulfonates of BBR have also been developed for small-molecule cancer immunotherapy, such as 2,3-methylenedioxy-9-((2,2,3,3-tetramethylcyclopropane-1-carbonyl) oxy)-10-methoxyprotoberberine chloride and 2,3-methylenedioxy-9-(2-(adamantan-1-yl) acetoxy)-10-methoxyberberine chloride ( Wang et al, 2018 ). BBR derivatives with a long alkyl chain branched by hydroxyl and methoxycarbonyl groups at position 9 showed 3.6-fold higher intracellular concentrations and 60-fold increased anti-proliferation activity against A549 cells compared with BBR ( Liu et al, 2020c ). 9-O-gernylberberrubine bromide and 9-O-farnesylberberrubine bromide showed greater growth inhibition, cell cycle regulation, and migration reduction ( Chang et al, 2021 ).…”

Section: Anticancer Effect Of Bbr Derivativesmentioning

confidence: 96%

Apoptosis Induction, a Sharp Edge of Berberine to Exert Anti-Cancer Effects, Focus on Breast, Lung, and Liver Cancer

et al. 2022

View full text Add to dashboard Cite

Cancer is the leading cause of death and one of the greatest barriers to increased life expectancy worldwide. Currently, chemotherapy with synthetic drugs remains one of the predominant ways for cancer treatment, which may lead to drug resistance and normal organ damage. Increasing researches have suggested that apoptosis, a type of programmed cell death, is a promising way for cancer therapy. Furthermore, natural products are important sources for finding new drugs with high availability, low cost and low toxicity. As a well-known isoquinoline alkaloid, accumulating evidence has revealed that berberine (BBR) exerts potential pro-apoptotic effects on multiple cancers, including breast, lung, liver, gastric, colorectal, pancreatic, and ovarian cancers. The related potential signal pathways are AMP-activated protein kinase, mitogen-activated protein kinase, and protein kinase B pathways. In this review, we provide a timely and comprehensive summary of the detailed molecular mechanisms of BBR in treating three types of cancer (breast, lung and liver cancer) by inducing apoptosis. Furthermore, we also discuss the existing challenges and strategies to improve BBR’s bioavailability. Hopefully, this review provides valuable information for the comprehension of BBR in treating three types of cancer and highlight the pro-apoptotic effects of BBR, which would be beneficial for the further development of this natural compound as an effective clinical drug for treating cancers.

show abstract

“…The series of 9-O-lipophilic derivatives synthesised by Liu et al [124] were designed to improve both the cell permeability and anticancer activity of berberine. Of the long alkyl chain derivatives bearing hydroxyl or methoxycarbonyl branch group, compound 20 was identified as a prototype lead compound with intracellular loading capacity of 3.6-fold better than berberine.…”

Section: The Berberine-o-derivativesmentioning

confidence: 99%

Recent Advances in Berberine Inspired Anticancer Approaches: From Drug Combination to Novel Formulation Technology and Derivatization

Habtemariam

2020

Molecules

View full text Add to dashboard Cite

Berberine is multifunctional natural product with potential to treat diverse pathological conditions. Its broad-spectrum anticancer effect through direct effect on cancer cell growth and metastasis have been established both in vitro and in vivo. The cellular targets that account to the anticancer effect of berberine are incredibly large and range from kinases (protein kinase B (Akt), mitogen activated protein kinases (MAPKs), cell cycle checkpoint kinases, etc.) and transcription factors to genes and protein regulators of cell survival, motility and death. The direct effect of berberine in cancer cells is however relatively weak and occur at moderate concentration range (10–100 µM) in most cancer cells. The poor pharmacokinetics profile resulting from poor absorption, efflux by permeability-glycoprotein (P-gc) and extensive metabolism in intestinal and hepatic cells are other dimensions of berberine’s limitation as anticancer agent. This communication addresses the research efforts during the last two decades that were devoted to enhancing the anticancer potential of berberine. Strategies highlighted include using berberine in combination with other chemotherapeutic agents either to reduce toxic side effects or enhance their anticancer effects; the various novel formulation approaches which by order of magnitude improved the pharmacokinetics of berberine; and semisynthetic approaches that enhanced potency by up to 100-fold.

show abstract

Berberine derivatives with a long alkyl chain branched by hydroxyl group and methoxycarbonyl group at 9-position show improved anti-proliferation activity and membrane permeability in A549 cells

Cited by 14 publications

References 43 publications

Biological Activity of Berberine—A Summary Update

Biological Activity of Berberine—A Summary Update

Apoptosis Induction, a Sharp Edge of Berberine to Exert Anti-Cancer Effects, Focus on Breast, Lung, and Liver Cancer

Recent Advances in Berberine Inspired Anticancer Approaches: From Drug Combination to Novel Formulation Technology and Derivatization

Contact Info

Product

Resources

About