Monocarbonyl Analogs of Curcumin with Potential to Treat Colorectal Cancer

Curcumin has a plethora of biological properties, making this compound potentially effective in the treatment of several diseases, including cancer. However, curcumin clinical use is compromised by its poor pharmacokinetics, being crucial to find novel analogs with better pharmacokinetic and pharmac...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry & biodiversity 2023-03, Vol.20 (3), p.e202300222-n/a
Main Authors: Clariano, Marta, Marques, Vanda, Vaz, João, Awam, Salma, Afonso, Marta B., Jesus Perry, Maria, Rodrigues, Cecília MP
Format: Article
Language:English
Subjects:
Analogs
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Apoptosis
Bioavailability
Biological properties
Cancer
Colorectal cancer
Colorectal carcinoma
Colorectal Neoplasms - drug therapy
Curcumin
curcumin monocarbonyl analogs
Evaluation
Hepatocytes
Humans
Liquid chromatography
NMR
Nuclear magnetic resonance
Pharmacokinetics
Pharmacology
Spectroscopy
Stability analysis
Toxicity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Curcumin has a plethora of biological properties, making this compound potentially effective in the treatment of several diseases, including cancer. However, curcumin clinical use is compromised by its poor pharmacokinetics, being crucial to find novel analogs with better pharmacokinetic and pharmacological properties. Here, we aimed to evaluate the stability, bioavailability and pharmacokinetic profiles of monocarbonyl analogs of curcumin. A small library of monocarbonyl analogs of curcumin 1a–q was synthesized. Lipophilicity and stability in physiological conditions were both assessed by HPLC‐UV, while two different methods assessed the electrophilic character of each compound monitored by NMR and by UV‐spectroscopy. The potential therapeutic effect of the analogs 1a–q was evaluated in human colon carcinoma cells and toxicity in immortalized hepatocytes. Our results showed that the curcumin analog 1e is a promising agent against colorectal cancer, with improved stability and efficacy/safety profile. Curcumin, a natural bioactive compound derived from Curcuma longa Linn., with antitumor activity. Curcumin's clinical use is compromised by its poor stability and bioavailability. Novel monocarbonyl analogs (1a–q) with improved pharmacokinetic properties were developed. 1e is a promising analog, being more stable and effective than curcumin as antitumoral agent while displaying lower toxicity in non‐tumor cells.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202300222