Synthesis and Antitumor Activity of Some Curcumin Analogs

Youssef, Khairia M.; El‐Sherbeny, Magda A.

doi:10.1002/ardp.200400939

Cited by 61 publications

(38 citation statements)

References 36 publications

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“…This imparts a rigid confirmation that has led to a broad spectrum of antitumor activity. The second generation curcumin derivative 2,6-bis ((3-methoxy-4-hydroxyphenyl) methylene)-cyclohexanone (BMHPC) was cytotoxic toward ER-breast cancer cells (IC 50 of 5.0 μM) and displayed anti-angiogenic properties in human and murine endothelial cell lines [18,21,49,50,[52][53][54][55][56][57][58][59].…”

Section: Synthetic Derivativesmentioning

confidence: 99%

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Curcumin and its derivatives in breast cancer: Current developments and potential for the treatment of drug-resistant cancers

Cridge¹,

Larsen²,

Rosengren³

2013

Oncol Discov

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Curcumin, a spice found in curry powder, is receiving considerable attention as a possible chemopreventative and chemotherapeutic. This review considers the evidence for the use of curcumin as a treatment for breast cancer, particularly triple negative breast cancers (lacking ER, PR and HER2) which are resistant to many current treatments. Evidence suggests that curcumin suppresses the growth of breast cancers both in vitro and in vivo. In ER-cell lines curcumin causes apoptosis via a range of mechanisms at concentrations ranging between 1 µM and 7.6 µM depending on the cell line and system. In xenograft models, curcumin has been shown to be effective but is limited by its bioavailability. This can be improved by nanotechnologies such as micelles. Studies with micelles have shown that these systems increase the uptake and cytotoxicity of curcumin in vitro. In xenotransplantation models micelles improved bioavailability and increased the half-life of curcumin while showing increases in apoptosis in implanted tumours. The last area discussed is the development of curcumin derivatives. Many of these show increased cytotoxicity (less than 1 µM) and improved pharmacokinetic profiles in vivo. The most potent of these compounds developed to date are RL66 and RL71 with IC 50 values less than 1 µM across a range of breast cancer cell lines, decreased metastasis in a xenograft model, decreased angiogenesis markers and improved tumour growth inhibition as compared to curcumin. Overall, this review concludes that curcumin and its derivatives show future potential as a powerful broad-spectrum treatment for breast cancer.

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Section: Synthetic Derivativesmentioning

confidence: 99%

“…Compound, 8 and 18 (Table 3) bearing the n-alkyl piperidone group showed potent cytotoxic activity towards various breast cancer cells [57]. This structure was recently further modified by replacing the methylene groups and the two doi: 10. carbonyl groups in curcumin by N-methyl-4 piperidone.…”

Section: Synthetic Derivativesmentioning

confidence: 99%

Curcumin and its derivatives in breast cancer: Current developments and potential for the treatment of drug-resistant cancers

Cridge¹,

Larsen²,

Rosengren³

2013

Oncol Discov

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“…It also exhibited highest cytotoxicity against HCT-116 and MCF-7 cells whereas dehydroxy-hispolon (182) showed maximum cytotoxicity against prostate PC-3 cells. Youssef and co-workers [123] have reported synthesis of monocarbonyl cyclic and noncyclic curcumin analogs (186-188) amongst which 188 elicited highest activity toward nonsmall lung cancer cell line.…”

Section: Appended Curcumin Mimics-appendedmentioning

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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“…Monoketo curcumin analogues with a piperidone ring impart a rigid confirmation that has led to a broad spectrum of antitumor activity. Compound, 8 and 18 (Table 1) bearing the nalkyl piperidone group showed potent cytotoxic activity towards various breast cancer cells (Youssef & El-Sherbeny, 2005). This structure was recently further modified by replacing the methylene groups and the two carbonyl groups in curcumin by N-methyl-4 piperidone.…”

Section: Prodrugs Analogues and Synthetic Derivativesmentioning

confidence: 99%