Ursolic acid derivative induces apoptosis in glioma cells through down-regulation of cAMP

Fan, Haitao; Geng, Li; Yang, Fan; Dong, Xushuai; He, Dong

doi:10.1016/j.ejmech.2019.04.059

Cited by 23 publications

(17 citation statements)

References 38 publications

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“…Among all these semisynthetic analogues, compounds 57 and 58 ( Figure 5 ) displayed excellent in vitro antiproliferative activities against Bel7402 cancer cells with IC 50 values of 0.02 µM and 0.01 µM, respectively [ 95 ]. Fan et al [ 96 ] synthesized a series of ursolic acid-based indole derivatives with compound 59 (p< 0.05) ( Figure 5 ), showing promising therapeutic effects against the growth of U251 and C6 glioma cells at a concentration of 10 μM. This compound inhibited glioma cell development, induced apoptosis, and cell cycle arrest in the G0/G1 phase with decreasing population in the G2/M and S phases via the down-regulation metabolic pathways.…”

Section: Indolementioning

confidence: 99%

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Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery

et al. 2021

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Pentacyclic triterpenoids are well-known phytochemicals with various biological activities commonly found in plants as secondary metabolites. The wide range of biological activities exhibited by triterpenoids has made them the most valuable sources of pharmacological agents. A number of novel triterpenoid derivatives with many skeletal modifications have been developed. The most important modifications are the formation of analogues or derivatives with nitrogen-containing heterocyclic scaffolds. The derivatives with nitrogen-containing heterocyclic compounds are among the most promising candidate for the development of novel therapeutic drugs. About 75% of FDA-approved drugs are nitrogen-containing heterocyclic moieties. The unique properties of heterocyclic compounds have encouraged many researchers to develop new triterpenoid analogous with pharmacological activities. In this review, we discuss recent advances of nitrogen-containing heterocyclic triterpenoids as potential therapeutic agents. This comprehensive review will assist medicinal chemists to understand new strategies that can result in the development of compounds with potential therapeutic efficacy.

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Section: Indolementioning

confidence: 99%

“…This compound inhibited glioma cell development, induced apoptosis, and cell cycle arrest in the G0/G1 phase with decreasing population in the G2/M and S phases via the down-regulation metabolic pathways. This compound is a potential anticancer agent for the treatment of glioma [ 96 ].…”

Section: Indolementioning

confidence: 99%

Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery

et al. 2021

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Section: Chemistry Of Uamentioning

confidence: 99%

“…The anticancer potential of the compound against glioma cells was studied. The compound demonstrated a good inhibition of cell proliferation and induced apoptosis when compared to the parent compound, UA [172]. An aromatic heterocyclic compound containing carbazole has attracted attention due its potential anticancer activity [173].…”

Section: Modification Of Miscellaneous Groupsmentioning

confidence: 99%

Ursolic Acid-Based Derivatives as Potential Anti-Cancer Agents: An Update

Khwaza

Oyedeji

Aderibigbe

2020

IJMS

133

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Ursolic acid is a pharmacologically active pentacyclic triterpenoid derived from medicinal plants, fruit, and vegetables. The pharmacological activities of ursolic acid have been extensively studied over the past few years and various reports have revealed that ursolic acid has multiple biological activities, which include anti-inflammatory, antioxidant, anti-cancer, etc. In terms of cancer treatment, ursolic acid interacts with a number of molecular targets that play an essential role in many cell signaling pathways. It suppresses transformation, inhibits proliferation, and induces apoptosis of tumor cells. Although ursolic acid has many benefits, its therapeutic applications in clinical medicine are limited by its poor bioavailability and absorption. To overcome such disadvantages, researchers around the globe have designed and developed synthetic ursolic acid derivatives with enhanced therapeutic effects by structurally modifying the parent skeleton of ursolic acid. These structurally modified compounds display enhanced therapeutic effects when compared to ursolic acid. This present review summarizes various synthesized derivatives of ursolic acid with anti-cancer activity which were reported from 2015 to date.

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“…Chemical modi cations on ring A of triterpenoids may lead to derivatives with cytotoxic activity [13][14][15]. Recently, raising attention is focused on the introduction of C2-benzylidene moiety into triterpene core which resulted in the derivatives with improved anti-in ammatory [16], anticancer [17][18][19] and antidiabetic [20] activities. Among them, 2-(4-nitrobenzylidene)-betulinic acid was active against ve different human cancer cell lines with IC 50 range from 1.36 to 3.5 μM [21].…”

Section: Introductionmentioning

confidence: 99%

Modification at A-Ring and Cytotoxic Activity of Betulonic Acid and its N-Methylpyperazinyl Amide

Giniyatullina¹,

Petrova

et al. 2021

Preprint

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Since cancer remains one of the most prevalent diseases today, there is an urgent need for the development of new agents. Triterpenoids may act in multiple pathways displaying antiproliferative, antiangiogenic, anti-inflammatory, and pro-apoptotic activities that place them as promising multifunctional agents in treating cancer. In this paper a series of betulonic acid and its N-methylpyperazinyl amide derivatives, especially holding C2-nicotinoylidene/furfurylidene/fluorobenzylidene fragments, have been synthesized and evaluated for their cytotoxic activity against the NCI-60 cancer cell line panel. N-Methylpiperazinyl amides of betulinic acid 11 and 4-pyridinoylidene-betulinic acid 9 as well as betulonic acid C2-4-pyridinoylidene- 14 or furfurylidene 16 derivatives were found to be the leading compounds with GI50 values of 0.49 μM for leukemia CCRF-CEM, 1.60 μM and 1.36 μM for colon cancer HCT-116 and 1.66 μM for melanoma LOX IMVI cell lines, respectively. The activity displayed for these compounds was higher than for the standard drug doxorubicin against colon cancer HCT-15 and ovarian cancer NCI/ADR-RES cell lines. Cell cycle analysis indicates that compound 11 promotes cytotoxic activity through the apoptosis induction both in conditionally normal (HEK293) and in cancer (A549, MCF-7) cells, whereas compound 14 exhibits both cytostatic and cytotoxic activity, dependently on cell line evaluated. In particular, in HEK293 cells the compound 14 induces mainly apoptotic cell death, while in A549 and MCF-7 cells cytostatic effect is dependent on cell cycle arrest in G2/M phase.Our results suggest that betulinic acid N-methylpyperazinyl amide 11 is the promising compound for the future drug development antitumor studies.

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Ursolic acid derivative induces apoptosis in glioma cells through down-regulation of cAMP

Cited by 23 publications

References 38 publications

Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery

Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery

Ursolic Acid-Based Derivatives as Potential Anti-Cancer Agents: An Update

Modification at A-Ring and Cytotoxic Activity of Betulonic Acid and its N-Methylpyperazinyl Amide

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