Synthesis and evaluation of curcumin-related compounds for anticancer activity

Wei, Xingchuan; Du, Zhiyun; Zheng, Xi; Cui, Xiaojie; Conney, Allan H.; Zhang, Kun

doi:10.1016/j.ejmech.2012.04.005

Cited by 86 publications

(61 citation statements)

References 48 publications

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“…Our previous study and another previous study indicated that cyclohexanone-containing analogues of curcumin have more potent anticancer activities than curcumin (23,24). Further modification of cyclohexanone-containing curcumin analogues by replacing the ortho-hydroxylmethoxyl benzene with a pyridine ring strongly enhanced the anticancer activities of these curcumin analogues (23).…”

Section: Discussionmentioning

confidence: 99%

“…Our previous study reported the synthesis and evaluation of five series of curcumin-related compounds (a total of 61 compounds) for their inhibitory effects on cultured prostate, pancreatic and colon cancer cells (23). The present study focused on pyridine analogues of curcumin, which are a subset of active compounds from our previous study.…”

Section: Discussionmentioning

confidence: 99%

“…Twelve pyridine analogues of curcumin ( Fig. 1) were synthesized by coupling the appropriate substituted benzaldehyde with cyclohexanone, cyclopentanone, tetrahydropyran-4-one or tetrahydrothiopyran-4-one, as previously described (23). Characterization of the compounds (2E,6E)-2,6-bis(pyridin-2/3/4-methylene)cyclohexanone (AN1/2/3), (2E,5E)-2,5-bis(pyridin-2/3/4-methyl ene)cyclopentanone (BN1/2/3), (3E, 5E)-3, 5-bis(pyri din-2/3/4-methylene)-tetrahydropyran-4-one (EN1/2/3) and (3E,5E)-3,5-bis(pyridin-2/3/4-methylene)-tetrahydrothio pyran-4-one (FN1/2/3) was previously described in detail (23).…”

Section: Methodsmentioning

confidence: 99%

“…It was determined that these pyridine analogues exhibited stronger inhibitory effects than curcumin on the growth of a number of human cancer cell lines, including human prostate cancer PC-3 cells (23). Therefore, the aim of the present study was to investigate the effects and mechanisms of several pyridine curcumin analogues in CWR-22Rv1 human prostate cancer cells, as CWR-22Rv1 cells exhibit ARs and thus were considered suitable to investigate AR activity.…”

Section: Introductionmentioning

confidence: 99%

“…In our previous study, we synthesized a series of 12 pyridine analogues of curcumin with cyclohexanone, cyclopentanone, tetrahydropyran-4-one or tetrahydrothiopyran-4-one linkers, and determined their anticancer activities in cultured human cancer cells (23). It was determined that these pyridine analogues exhibited stronger inhibitory effects than curcumin on the growth of a number of human cancer cell lines, including human prostate cancer PC-3 cells (23).…”

Section: Introductionmentioning

confidence: 99%

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Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Zhou

Zhao

et al. 2016

Oncology Letters

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Abstract. The concentrations required for curcumin to exert its anticancer activity (IC 50 , 20 µM) are difficult to achieve in the blood plasma of patients, due to the low bioavailability of the compound. Therefore, much effort has been devoted to the development of curcumin analogues that exhibit stronger anticancer activity and a lower IC 50 than curcumin. The present study investigated twelve pyridine analogues of curcumin, labeled as groups AN, BN, EN and FN, to determine their effects in CWR-22Rv1 human prostate cancer cells. The inhibitory effects of these compounds on testosterone (TT)-induced androgen receptor (AR) activity was determined by performing an AR-linked luciferase assay and by TT-induced expression of prostate-specific antigen.The results of the current study suggested that the FN group of analogues had the strongest inhibitory effect of growth on CWR-22Rv1 cultured cells, and were the most potent inhibitor of AR activity compared with curcumin, and the AN, BN and EN analogues. Thus, the results of the present study indicate the inhibition of the AR pathways as a potential mechanism for the anticancer effect of curcumin analogues in human prostate cancer cells. Furthermore, curcumin analogues with pyridine as a distal ring and tetrahydrothiopyran-4-one as a linker may be good candidates for the development of novel drugs for the treatment of prostate cancer, by targeting the AR signaling pathway. IntroductionProstate cancer is the second most common cause of cancer-related mortality in American men. The androgen receptor (AR) is a ligand-activated steroid hormone receptor that regulates normal prostate development and function (1). It is also critical in the development and progression of prostate cancer (2). Current therapeutic strategies for prostate cancer, such as androgen ablation therapy, inhibit AR function (3). A combination of androgen synthesis suppression and AR inhibition may be used as a more aggressive form therapy (4). Therefore, identification of the chemical agents and mechanisms that inhibit AR signaling warrant further investigation for the development of novel prostate cancer therapeutics.Curcumin is a non-nutritive yellow pigment found in turmeric, a rhizome-derivative of the plant Curcuma longa Linn. Numerous studies have demonstrated the anticancer activity of curcumin and curcumin analogues in animal models (5-10), as well as the effects on cell growth and apoptosis in vitro (11)(12)(13)(14)(15)(16)(17)(18)(19). However, it should be noted that the clinical efficacy of curcumin is limited, possibly due to its low bioavailability (20)(21)(22).In our previous study, we synthesized a series of 12 pyridine analogues of curcumin with cyclohexanone, cyclopentanone, tetrahydropyran-4-one or tetrahydrothiopyran-4-one linkers, and determined their anticancer activities in cultured human cancer cells (23). It was determined that these pyridine analogues exhibited stronger inhibitory effects than curcumin on the growth of a number of human cancer cell lines, including human pros...

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Zhou

Zhao

et al. 2016

Oncology Letters

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Curcuminoids in Multi‐Component Synthesis

Ajavakom

Yutthaseri

Chantanatrakul

et al. 2017

Journal of Heterocyclic Chem

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The introduction of a 1,3‐dicarbonyl unit in curcuminoid derivatives for multi‐component reactions (MCRs) to furnish six‐membered heterocyclic compounds has been reviewed. Attention has focused on the assembly of the three‐component Biginelli reactions relating to curcumin or tetrahydrocurcumin (THC), aromatic aldehydes and urea as substrates. The hybrid molecules of two bioactive agents were designed and synthesized by using these MCRs concepts. The four‐component modified Hantzsch condensation was the latest development of this synthetic route. The possible mechanism of the MCRs of both curcumin and THC were also summarized.

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Facile synthesis of deuterated and [¹⁴C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools

Gordon

Graham

Schneider

2013

J. Label Compd. Radiopharm

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Curcumin is a dietary diphenol with antioxidant, antinflammatory and antitumor activity. We describe facile procedures for the synthesis of [14C2]curcumin (4 mCi/mmol), [d6]curcumin, [d3]curcumin, [13C5]curcumin, and [d6]bicyclopentadione, the major oxidative metabolite of curcumin. We also describe synthesis of the labeled building blocks [14C]vanillin, [d3]vanillin, and [13C5]acetylacetone. The overall molar yields of the labeled products were 52% ([14C]) and 47% ([d3]) for vanillin and 25% ([14C2]) and 27% ([d6]) for curcumin. The compounds can be used as radiotracers in biotransformation studies and as isotopic standards for mass spectrometry-based quantification in pharmacokinetic analyses.

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Synthesis and evaluation of curcumin-related compounds for anticancer activity

Cited by 86 publications

References 48 publications

Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Curcuminoids in Multi‐Component Synthesis

Facile synthesis of deuterated and [¹⁴C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools

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Synthesis and evaluation of curcumin-related compounds for anticancer activity

Cited by 86 publications

References 48 publications

Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Pyridine analogues of curcumin exhibit high activity for inhibiting CWR-22Rv1 human prostate cancer cell growth and androgen receptor activation

Curcuminoids in Multi‐Component Synthesis

Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools

Contact Info

Product

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Facile synthesis of deuterated and [¹⁴C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools