ChemInform Abstract: 1,5‐Diphenyl‐1,4‐pentadiene‐3‐ones and Cyclic Analogues as Antioxidative Agents. Synthesis and Structure‐Activity Relationship.

Sardjiman, S.S.; Reksohadiprodjo, M.S.; Hakim, Lukman; Goot, H. Van Der; Timmerman, H.

doi:10.1002/chin.199747108

Cited by 4 publications

(6 citation statements)

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“…Previously, the curcumin analogues HGV-0 and GVT-0 have been shown to act as potent antiinflammatory agents [12]. Local inflammation plays a role carcinogenesis.…”

Section: Discussionmentioning

confidence: 99%

“…Two analogues of curcumin, hexagamavunone (HGV-0) and gamavutone-0 (GVT-0), were synthesized in 1954 using the Rumpel method with some modifications [12]. These compounds are reported to have antitumor activities [13].…”

Section: Introductionmentioning

confidence: 99%

“…These compounds are reported to have antitumor activities [13]. In addition, HGV-0 possesses anti-inflammatory activity through its inhibition of COX enzyme activity [12,13], with IC 50 values of 8.15 M and 8.02 M [12].…”

Section: Introductionmentioning

confidence: 99%

“…The other curcumin analogue, GVT-0, also has antioxidant, anti-inflammatory, antitumor, antibacterial, and antifungal activities [12]. Another report shows that GVT-0 has a potent anti-proliferative effect because it inhibits endothelial cell proliferation by 96.6 % at a concentration of 3 g/mL [14].…”

Section: Introductionmentioning

confidence: 99%

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Chemopreventive properties of curcumin analogues, hexagamavunone-0 and gamavutone-0, in rat colorectal cancer model

Yulianty¹,

Hakim²,

Sardjiman³

et al. 2017

Trop. J. Pharm Res

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Purpose: To examine the chemopreventive activity of curcumin analogues, hexagamavunone-0 (HGV-0) and gamavutone-0 (GVT-0), compared to curcumin in a colorectal cancer model in Wistar rats. Methods: Rats (n = 25) were assigned to one of five groups (n = 5 in each group). Colorectal cancer was induced in the control group with subcutaneous injection of 1,2-dimethylhydrazine (DMH) 60 mg/kg once a week for 15 weeks. In addition to DMH injection, treatment groups were treated with curcumin (20, 40, or 80 mg/kg),20, 40, or 80 mg/kg), and hexagamavunone 20, 40, or 80 mg/kg) orally twice a week for 15 weeks. The number and volume of nodules in the colorectal area were observed after laparatomy. Histopathological analysis was performed using H & E staining and immunohistochemistry with antibodies against adenomatous polyposis coli (APC) and cyclooxygenase 2 (COX-2). Results: All treatments reduced colorectal nodule volume, but only HGV-0 significantly decreased the numbers of nodules compared to DMH controls (p < 0.05). The reduction was 96.1 % with 40 mg/kg HGV-0. Mutated APC expression was inhibited by curcumin, GVT-0, and HGV-0 at a dose of 40 mg/kg, whereas COX-2 expression was mostly inhibited by

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“…Previously, the curcumin analogues HGV-0 and GVT-0 have been shown to act as potent antiinflammatory agents [12]. Local inflammation plays a role carcinogenesis.…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Chemopreventive properties of curcumin analogues, hexagamavunone-0 and gamavutone-0, in rat colorectal cancer model

Yulianty¹,

Hakim²,

Sardjiman³

et al. 2017

Trop. J. Pharm Res

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“…Some of the analogs that we focus on are PGV-0, Hexagamavunone-5 (HGV-5) and Hexagamavunone-7 (HGV-7). PGV-0 is a promising anti-inflammatory agent, HGV-5 has a potent antioxidant activity and HGV-7 is more potent as antibacterial agent against S. pneumonia than PGV-0 and curcumin (Sardjiman, 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tetrahydrohexagamavunon-5 and Tetrahydrohexagamavunon-7

Ritmaleni

Praditya

Wibowo

et al. 2015

Indonesian J. Pharm.

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Synthesis of Tetrahydrohexagamavunon-5 (THHGV-5) and Tetrahydrohexagamavunone-7 (THHGV-7) were prepared by catalytic hydrogenation reaction on Hexagamavunon-5 (HGV-5) and Hexagamavunone-7 (HGV-7) by using gas H 2 as source of hydrogen gas, Pd/C 10 % as metal catalyst and methanol as solvent at room temperature. According to previous study, Pd/C catalyst is more specific than other metal catalyst to reduce α,β-unsaturated double bond without reduction of its carbonyl functional group.

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In Silico Pharmacokinetics Study of 2,5-Dibenzylidenecyclopentanone Analogs as Mono-Ketone Versions of Curcumin

Marbun,

Hakim,

Sri Octa Ujiantari

et al. 2023

BIO Web Conf.

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The absorption-distribution-metabolism-excretion (ADME) profile is a crucial parameter that indicates the pharmacokinetics of the drug. The pharmacokinetic properties of a drug represent the fate of the drug in the body. Curcumin is a main compound in turmeric produced by plants of the Curcuma longa species, and has several pharmacological effects in animal and human clinical studies. However, preclinical and clinical studies have shown that curcumin has pharmacokinetic limitations such as poor bioavailability and rapid metabolism which restrict its widespread use. Therefore, various modifications and synthesis of some analogs using curcumin as a lead compound with variations in the main structure and attached substituents have been carried out to explore the pharmacological effects as drug candidates. One of the widely developed methods is the modification of curcumin’s main structure, specifically the conversion from diketone to mono-ketone.In 1997, 2,5-dibenzylidene cyclopentanone analogs were synthesized and their biological activity were performed. However, there is no further information related their pharmacokinetic properties. Therefore, those properties were predicted by performing ADME calculation in two online servers, ADMETsar 2.0 and ADMETlab 2.0.. By utilizing the online servers ADMETsar 2.0, and ADMETLab 2.0 for in-silico screening of pharmacokinetic properties, from the 17 compounds, it was found that the variation among pharmacokinetic aspects was observed, either decreasing or increasing drug likeness properties of 2,5-dibenzylidene cyclopentanone analogs compared to curcumin. In addition, the interaction those analogs with protein or enzymes involved during ADME process such as blood plasma protein (albumin), p-Glycoprotein, and CYP3A4 was evaluated by performing molecular docking.. The docking results showed a sufficiently positive correlation with ADME screening outcomes.

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ChemInform Abstract: 1,5‐Diphenyl‐1,4‐pentadiene‐3‐ones and Cyclic Analogues as Antioxidative Agents. Synthesis and Structure‐Activity Relationship.

Cited by 4 publications

References 1 publication

Chemopreventive properties of curcumin analogues, hexagamavunone-0 and gamavutone-0, in rat colorectal cancer model

Chemopreventive properties of curcumin analogues, hexagamavunone-0 and gamavutone-0, in rat colorectal cancer model

Synthesis of Tetrahydrohexagamavunon-5 and Tetrahydrohexagamavunon-7

In Silico Pharmacokinetics Study of 2,5-Dibenzylidenecyclopentanone Analogs as Mono-Ketone Versions of Curcumin

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