Synthetic derivatives of natural cinnamic acids as potential anti‐colorectal cancer agents

Falbo, Federica; Gemma, Sandra; Koch, Adrian; Mazzotta, Sarah; Carullo, Gabriele; Ramunno, Anna; Butini, Stefania; Schneider‐Stock, Regine; Campiani, Giuseppe; Aiello, Francesca

doi:10.1111/cbdd.14415

Chem Biol Drug Des

2023

DOI: 10.1111/cbdd.14415

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Synthetic derivatives of natural cinnamic acids as potential anti‐colorectal cancer agents

Federica Falbo,

Sandra Gemma,

Adrian Koch

et al.

Abstract: Cinnamic acid and its derivatives represent attractive building blocks for the development of pharmacological tools. A series of piperoniloyl and cinnamoyl‐based amides (6‐9 a‐f) have been synthesized and assayed against a wide panel of colorectal cancer (CRC) cells, with the aim of finding promising anticancer agents. Among all twenty‐four synthesized molecules, 7a, 7e‐f, 9c, and 9f displayed the best antiproliferative activity. The induced G1 cell cycle arrest and the increase in apoptotic cell death was see… Show more

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Cited by 3 publications

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Improving trans‐cinnamic acid production in a model cyanobacterium

Hunstiger,

Ma,

Paton

et al. 2024

Biotechnology Progress

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Abstracttrans‐Cinnamic acid (tCA) is a precursor in the synthesis of many high‐value compounds with bio‐active qualities useful in applications like medicine, polymers, and cosmetics. Currently tCA is produced by industrial chemical synthesis from fossil fuels or cost‐prohibitive isolation from terrestrial plants. Cyanobacteria, a type of photosynthetic bacteria, can be readily engineered to convert sunlight and carbon dioxide into metabolites of interest at relatively high amounts compared to terrestrial plants. The purpose of this study is to advance the industrial and commercial value of cyanobacteria as a biological factory for renewable production of tCA. Production of tCA has previously been demonstrated in the model cyanobacterium Synechocystis sp. PCC 6803 (S. 6803) via expression of non‐native phenylalanine ammonia lyase (PAL) from various organisms. This project focuses on developing and characterizing a new high‐titer strain of S. 6803 expressing a plant PAL gene controlled by an inducible promoter. We assessed production in shake flasks under constant light, a 12 h:12 h light:dark cycle, and environmental photobioreactors (ePBRs) with a sinusoidal, rapidly fluctuating light environment. Our strain demonstrates a four‐fold increase in tCA production to ~500 mg L−1 by 14 days compared to previously reported titers in S. 6803 under shake flask cultivation and a 30–50% improved average tCA production per culture density (60 mg·L−1·OD730−1) in ePBRs over comparable previously reported culture methods. Our study progresses S. 6803 tCA bioproduction into higher culture volumes, up to 500 mL, while further validating the strength of an inducible system for tCA production in S. 6803.

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Improving trans‐cinnamic acid production in a model cyanobacterium

Hunstiger,

Ma,

Paton

et al. 2024

Biotechnology Progress

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A Review of Cinnamic Acid’s Skeleton Modification: Features for Antibacterial-Agent-Guided Derivatives

Annuur,

Triana,

Ernawati

et al. 2024

Molecules

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Antimicrobial resistance has emerged as a significant danger to global health, and the need for more effective antimicrobial resistance (AMR) control has been highlighted. Cinnamic acid is abundant in plant products and is a potential starting material for further modification, focusing on the development of new antimicrobial compounds. In the following review, we describe the classification of critical antibacterial-guided reactions applied to the main skeleton structure of cinnamic acid derivatives over the last decade. Of all of the main parts of cinnamic acids, the phenyl ring and the carboxylic group significantly affect antibacterial activity. The results presented in the following review can provide valuable insights into considerable features in the organic modification of cinnamic acids related to antibacterial medication development and the food industry.

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Common Mitochondrial Targets of Curcumin and Cinnamic Acid, the Membrane-Active Natural Phenolic Compounds

Fedotcheva,

Beloborodova,

Fedotcheva

2024

Pharmaceutics

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Background: Research has shown the multiple actions of curcumin on different cell systems, including enzymes and mitochondria. The detected effects of curcumin on mitochondria are diverse, ranging from protective to toxic. Objectives: In this present work, the influence of curcumin, as well as cinnamic acid, which is a microbial metabolite and a possible product of the microbial breakdown of curcumin, on isolated mitochondria, was investigated. Methods: Membrane potential, swelling, respiration, and calcium retention capacity were studied using selective electrodes, fluorescence and spectral methods. Results: It was found that curcumin at low concentrations (10–20 μM) activated the opening of the calcium-dependent permeability transition pore (mPTP) and decreased the calcium retention capacity and threshold concentrations necessary for the mPTP opening. Moreover, curcumin caused a concentration-dependent stepwise decrease in the membrane potential, accompanied by the activation of respiration and a decrease in oxidative phosphorylation, which indicates that curcumin is a typical mitochondrial uncoupler. The uncoupling effect strongly depended on the concentration of curcumin, which also increased, stepwise, from weak uncoupling at 25 µM to complete uncoupling at 75–100 µM. Cinnamic acid had similar effects, with the exception of the depolarizing effect, at concentrations that were an order of magnitude higher. Conclusions: Presumably, the uncoupling action of curcumin is a priming event that modulates any energy- and redox-dependent mitochondrial functions, from positive stimulation to toxic disorder. This effect can also underlie the curcumin-induced changes in different cellular processes and be achieved by targeted delivery of curcumin to certain cells, bypassing the microbiota.

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Synthetic derivatives of natural cinnamic acids as potential anti‐colorectal cancer agents

Cited by 3 publications

References 34 publications

Improving trans‐cinnamic acid production in a model cyanobacterium

Improving trans‐cinnamic acid production in a model cyanobacterium

A Review of Cinnamic Acid’s Skeleton Modification: Features for Antibacterial-Agent-Guided Derivatives

Common Mitochondrial Targets of Curcumin and Cinnamic Acid, the Membrane-Active Natural Phenolic Compounds

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