Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties

Dubey, Shiv Kumar; Sharma, Anuj Kumar; Narain, Upma; Misra, Krishna; Pati, Uttam

doi:10.1016/j.ejmech.2007.11.027

Cited by 85 publications

(49 citation statements)

References 19 publications

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“…Previous curcumin prodrugs have been synthesized with amino acids and piperic acid as promoieties. 29,30 Recently, polymeric prodrugs with drug molecules conjugated to a polymer backbone such as polyethylene glycol (PEG) and polyvinylpyrrolidone have shown promise in drug delivery. [31][32][33] The use of PEG as a promoiety to attach to drug molecules known as PEGylation is an accepted strategy for human therapy that takes advantage of the safety profile of PEG.…”

Section: Introductionmentioning

confidence: 99%

Effects of Different Carboxylic Ester Spacers on Chemical Stability, Release Characteristics, and Anticancer Activity of Mono-PEGylated Curcumin Conjugates

Wichitnithad

Nimmannit

Callery

et al. 2011

Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 99%

Effects of Different Carboxylic Ester Spacers on Chemical Stability, Release Characteristics, and Anticancer Activity of Mono-PEGylated Curcumin Conjugates

Wichitnithad

Nimmannit

Callery

et al. 2011

Journal of Pharmaceutical Sciences

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“…Most of the analogs were found to inhibit TrxR in the low micromolar range. Structure-activity relationship analysis revealed that analogs with furan moiety (44)(45)(46)(47) have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogs with TrxR. The compound 46 showed growth inhibitory activity against different TrxR over-expressed A549/R and MCF-7/R cancer cell lines.…”

Section: Modifications Of Aryl Sidementioning

confidence: 97%

“…The curcumin -glucoside was only cleaved by beta-glucosidases andgalactosidases, but not by pancreatic lipase or hepatic esterase, suggesting that these enzymes are crucial for the bioactivation and cytotoxicity of these glycoconjugates. Dubey et al [44] have synthesized the monoesters of curcumin, a symmetric diphenol with valine (18) and glycine (19) substituents, by solid phase synthesis and its diesters by solution phase method. The assessment of their anti-proliferative activities suggested that the diesters are relatively more active than curcumin itself against KB and HeLa cell lines probably due to their increased solubility, slow metabolism and better cellular uptake.…”

Section: Modifications Of Aryl Sidementioning

confidence: 99%

Perspectives on New Synthetic Curcumin Analogs and their Potential Anticancer Properties

Vyas¹,

Dandawate²,

Padhyé³

et al. 2013

Current Pharmaceutical Design

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Curcumin is the active component of dried rhizome of Curcuma longa, a perennial herb belonging to ginger family, cultivated extensively in south and southeastern tropical Asia. It is widely consumed in the Indian subcontinent, south Asia and Japan in traditional food recipes. Extensive research over last few decades has shown that curcumin is a potent anti-inflammatory agent with powerful therapeutic potential against a variety of cancers. It suppresses proliferation and metastasis of human tumors through regulation of various transcription factors, growth factors, inflammatory cytokines, protein kinases and other enzymes. It induces apoptotic cell death and also inhibits proliferation of cancer cells by cell cycle arrest. Pharmacokinetic data has shown that curcumin undergoes rapid metabolism leading to glucuronidation and sulfation in the liver and excretion in the feces, which accounts for its poor systemic bioavailability. The compound has, therefore, been formulated and administered using different drug delivery systems such as liposomes, micelles, polysaccharides, phospholipid complexes and nanoparticles that can overcome the limitation of bioavailability to some extent. Attempts to avoid rapid metabolism of curcumin until now have been met with limited success. This has prompted researchers to look for new synthetic curcumin analogs in order to overcome the drawbacks of limited bioavailability and rapid metabolism, and gain efficacy with reduced toxicity. In this review we provide a summarized account of novel synthetic curcumin formulations and analogs, and the recent progress in the field of cancer prevention and treatment.

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“…Several amino acid conjugates of curcumin have been recently prepared, and their antiproliferative properties have been briefly studied without report of their effect on any molecular target (15). Since the proteasome has been identified as a potential target of curcumin, we aimed to assess whether the amino acid conjugates of curcumin have any inhibition activity on the proteasome.…”

Section: Bioassay Of Curcumin Monoacetate and Curcumin Diacetatementioning

confidence: 99%

Evaluation of curcumin acetates and amino acid conjugates as proteasome inhibitors

Wan

Yang²,

Zhou³

et al. 2010

Int J Mol Med

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Abstract. Curcumin (diferuloylmethane) is the main active ingredient of turmeric, a traditional herbal medicine and food of south Asia. Curcumin has been found to have a wide range of biological activities, including antioxidant, anti-inflammatory, chemopreventive and chemotherapeutic activities. Curcumin is currently being tested in clinical trials for treatment of various types of cancers, including multiple myeloma, pancreatic cancer and colon cancer. Although no toxicity associated with curcumin (even at very high doses) has been observed, the effects of curcumin in other solid tumors have been modest, primarily due to poor water solubility and poor bioavailability in tissues remote from the gastrointestinal tract. Therefore, there is a need for the discovery of curcumin analogs with better water solubility or greater bioavailability for the treatment of solid tumors such as prostate cancer. In this study, curcumin acetates and amino acid conjugates of curcumin were studied in terms of their proteasome inhibitory and antiproliferative effects against several human cancer cell lines. It was found that the water soluble amino acid conjugates of curcumin showed a potent antiproliferative effect and are potent proteasome inhibitors. Docking studies of the curcumin amino acid conjugates for proteasome inhibition were carried out to explain their biological activities. It is suggested that they may serve as the water soluble analogs of curcumin.

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Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties

Cited by 85 publications

References 19 publications

Effects of Different Carboxylic Ester Spacers on Chemical Stability, Release Characteristics, and Anticancer Activity of Mono-PEGylated Curcumin Conjugates

Effects of Different Carboxylic Ester Spacers on Chemical Stability, Release Characteristics, and Anticancer Activity of Mono-PEGylated Curcumin Conjugates

Perspectives on New Synthetic Curcumin Analogs and their Potential Anticancer Properties

Evaluation of curcumin acetates and amino acid conjugates as proteasome inhibitors

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