Monocarbonyl Analogs of Curcumin with Potential to Treat Colorectal Cancer. Issue 3 (6th March 2023)

• Record Type: Journal Article
• Authors: Clariano, Marta; Marques, Vanda; Vaz, João; Awam, Salma; Afonso, Marta B.; Jesus Perry, Maria; Rodrigues, Cecília MP
• Is Part Of: Chemistry & biodiversity. Volume 20:Issue 3(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-03-06
• Subjects: curcumin -- curcumin monocarbonyl analogs -- cancer -- apoptosis; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.202300222
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract: 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. Abstract : 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.