Synthesis, anticancer, and antibacterial activities of piplartine derivatives on cell cycle regulation and growth inhibition

Kumar, Jonnala Ujwal; Shankaraiah, G.; Kumar, R Sateesh Chandra; Pitke, Vikrant Vinay; Rao, Guo-Wu; Poornima, B.; Babu, K. Suresh; Sreedhar, Amere Subbarao

doi:10.1080/10286020.2013.769965

Cited by 7 publications

(5 citation statements)

References 22 publications

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“…Piplartine was modified on heterocyclic ring via Baylis-Hillman reaction. The derivatives were determined anticancer activity [46]. In HeLa and IMR-32 cells, amides S11e13 were demonstrated to enforced cell cycle inhibition arresting cells in G2-M phase of the cell cycle ( Fig.…”

Section: Synthetic Tmca Amides As Antitumor Agentsmentioning

confidence: 99%

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Zhao

Song

Xie

et al. 2019

European Journal of Medicinal Chemistry

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a b s t r a c t TMCA (3,4,5-trimethoxycinnamic acid) ester and amide are privileged structural scaffolds in drug discovery which are widely distributed in natural products and consequently produced diverse therapeutically relevant pharmacological functions. Owing to the potential of TMCA ester and amide analogues as therapeutic agents, researches on chemical syntheses and modifications have been carried out to druglike candidates with broad range of medicinal properties such as antitumor, antiviral, CNS (central nervous system) agents, antimicrobial, anti-inflammatory and hematologic agents for a long time. At the same time, SAR (structure-activity relationship) studies have draw greater attention among medicinal chemists, and many of the lead compounds were derived for various disease targets. However, there is an urgent need for the medicinal chemists to further exploit the precursor in developing chemical entities with promising bioactivity and druggability. This review concisely summarizes the synthesis and biological activity for TMCA ester and amide analogues. It also comprehensively reveals the relationship of significant biological activities along with SAR studies.

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Section: Synthetic Tmca Amides As Antitumor Agentsmentioning

confidence: 99%

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Zhao

Song

Xie

et al. 2019

European Journal of Medicinal Chemistry

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“…Moreover, piperine and piperlongumine, two piperamide compounds, exhibit activity across a range of bacteria, including Gram-positive and Gram-negative species [16]. Synthetic piplartine derivatives also exhibit antibiotic activity against S. aureus and Pseudomonas aeruginosa [17].…”

Section: Introductionmentioning

confidence: 99%

Toxicity and Teratogenic Potential of Piplartine from Piper tuberculatum Jacq. during Embryonic Development in Mice (Mus musculus)

Silva,

Miranda,

da Silva

et al. 2024

DDC

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Piplartine, also known as piperlongumine, is a natural and biologically active amide alkaloid found in various Piper species within the Piperaceae family. It possesses numerous beneficial properties that can be leveraged in the development of nanotechnological and pharmaceutical products. However, information on the effects of piplartine on mammalian embryonic development is scarce. This study aims to assess the general toxicity and teratogenic potential of piplartine during the embryonic development of mice. Pregnant mice received daily treatments of 25, 50, or 100 mg/kg of piplartine via gavage from the sixth day of gestation (implantation) to the eighteenth. On the eighteenth day, the mice were euthanized, and whole organs, blood samples (for hematological and biochemical analyses), and bone marrow cells (for DNA fragmentation and cell cycle assays) were collected. The uterus was examined for implantation sites and embryo resorptions. Additionally, fetuses were collected to assess for fetal anomalies. Piplartine did not result in maternal or embryo-fetal toxicity, induce fetal anomalies, cause hematological and biochemical alterations, or lead to DNA fragmentation. The oral administration of piplartine is safe and does not exhibit toxicity or teratogenic effects in mice. This finding opens avenues for the development of piplartine-based biotechnological products for therapeutic interventions in disease treatment.

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“…Previous reports indicate that PPL also has functions at the molecular level and evokes apoptotic cell death through the alteration of differing pathways, such as phosphatidylinositol 3-kinase (PI3K)/serine/threonine protein kinase (Akt) and mammalian target of rapamycin (mTOR) (PI3K/Akt/mTOR), nuclear factor kappa B (NF-κB), Janus kinase-signal transducer and activator of transcription-3 (JAK1, 2/STAT3), and JNK, in cancer-derived cell lines [21]. Regarding the synthetic derivatives of PPL, there are reports of bioactivity against two different human tumor cell lines, human neuroblastoma (IMR-32) and cervical cancer (HeLa) cells [22], while in a study on a PPL analog, the ester, ( E )-benzhydryl 3-(3,4,5-trimethoxyphenyl) acrylate, was shown to be cytotoxic against U87MG cell line [23].…”

Section: Introductionmentioning

confidence: 99%

NFBTA: A Potent Cytotoxic Agent against Glioblastoma

et al. 2019

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Piplartine (PPL), also known as piperlongumine, is a biologically active alkaloid extracted from the Piper genus which has been found to have highly effective anticancer activity against several tumor cell lines. This study investigates in detail the antitumoral potential of a PPL analogue; (E)-N-(4-fluorobenzyl)-3-(3,4,5-trimethoxyphenyl) acrylamide (NFBTA). The anticancer potential of NFBTA on the glioblastoma multiforme (GBM) cell line (U87MG) was determined by 3-(4,5-dimethyl-2-thia-zolyl)-2, 5-diphenyl-2H-tetrazolium bromide (MTT), and lactate dehydrogenase (LDH) release analysis, and the selectivity index (SI) was calculated. To detect cell apoptosis, fluorescent staining via flow cytometry and Hoechst 33258 staining were performed. Oxidative alterations were assessed via colorimetric measurement methods. Alterations in expressions of key genes related to carcinogenesis were determined. Additionally, in terms of NFBTA cytotoxic, oxidative, and genotoxic damage potential, the biosafety of this novel agent was evaluated in cultured human whole blood cells. Cell viability analyses revealed that NFBTA exhibited strong cytotoxic activity in cultured U87MG cells, with high selectivity and inhibitory activity in apoptotic processes, as well as potential for altering the principal molecular genetic responses in U87MG cell growth. Molecular docking studies strongly suggested a plausible anti-proliferative mechanism for NBFTA. The results of the experimental in vitro human glioblastoma model and computational approach revealed promising cytotoxic activity for NFBTA, helping to orient further studies evaluating its antitumor profile for safe and effective therapeutic applications.

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Synthesis, anticancer, and antibacterial activities of piplartine derivatives on cell cycle regulation and growth inhibition

Cited by 7 publications

References 22 publications

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Toxicity and Teratogenic Potential of Piplartine from Piper tuberculatum Jacq. during Embryonic Development in Mice (Mus musculus)

NFBTA: A Potent Cytotoxic Agent against Glioblastoma

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