Development of C-20 modified betulinic acid derivatives as antitumor agents

Kim, Jin Yung; Koo, Han-Mo; Kim, Darrick S. H. L.

doi:10.1016/s0960-894x(01)00460-7

Cited by 83 publications

(45 citation statements)

References 15 publications

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“…In the past, researchers found that the cytotoxicity of betulinic acid decreases by forming alkyl or aryl esters from 28-carboxylic group. (Kim et al, 1998(Kim et al, , 2001Kvasnica et al, 2005;Urban et al, , 2005. One of the explanations of this fact is that free carboxyl group is responsible for the activity and the hydrolysis of its esters is extremely difficult and requires extreme conditions which are caused by sterical hinderance of the neopentyl-type group.…”

Section: Derivatization Of Betulinic (1) and Pulsatillic Acid (2) In mentioning

confidence: 99%

“…This fact dramatically improves their therapeutic index for testing anti-HIV activity Fujioka et al, 1994, Mayaux et al, 1994. A comparison of activity of betulinic (1) and dihydrobetulinic acid (38) with their acetates is described in (Kim et al, 2001;Mukherjee et al, 2004). Tests with SK-MEL-2 and M14-MEL lines showed that the acetylation of hydroxyderivatives causes either a small decrease or no change in cytotoxicity (Kim et al, 2001).…”

Section: Derivatization Of Betulinic Acid (1) and Betulin (3) In Posimentioning

confidence: 99%

“…A comparison of activity of betulinic (1) and dihydrobetulinic acid (38) with their acetates is described in (Kim et al, 2001;Mukherjee et al, 2004). Tests with SK-MEL-2 and M14-MEL lines showed that the acetylation of hydroxyderivatives causes either a small decrease or no change in cytotoxicity (Kim et al, 2001). This fact is in good agreement with the work, where the influence of the 3-O-acetyl group on cytotoxicity of broader group of triterpenoides 65 -67 was studied (Mukherjee et al, 2004;Sarek et al, 2005).…”

Section: Derivatization Of Betulinic Acid (1) and Betulin (3) In Posimentioning

confidence: 99%

“…Another option to modify the isopropenyl side chain is substitution, respectively allylic oxidation. Introducing alcohol moieties into the location 30 might be carried out either by allylic bromination using NBS followed by nucleofilic substitution (Kim et al, 2001) or allylic oxidation followed with reduction (Biedermann et al, 2005). The most unique compound among these oxygenated derivatives is the unsaturated aldehyde 90, synthesized by allylic oxidation of acid 1 by selenium dioxide.…”

Section: Modification Of Skeleton Of Betulinic Acid (1) On the Isopromentioning

confidence: 99%

See 3 more Smart Citations

The Potential of Triterpenoids in the Treatment of Melanoma

Šarek¹,

Kvasnica²,

Vlk³

et al. 2011

Research on Melanoma - A Glimpse Into Current Directions and Future Trends

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Section: Derivatization Of Betulinic (1) and Pulsatillic Acid (2) In mentioning

confidence: 99%

Section: Derivatization Of Betulinic Acid (1) and Betulin (3) In Posimentioning

confidence: 99%

Section: Derivatization Of Betulinic Acid (1) and Betulin (3) In Posimentioning

confidence: 99%

Section: Modification Of Skeleton Of Betulinic Acid (1) On the Isopromentioning

confidence: 99%

See 2 more Smart Citations

The Potential of Triterpenoids in the Treatment of Melanoma

Šarek¹,

Kvasnica²,

Vlk³

et al. 2011

Research on Melanoma - A Glimpse Into Current Directions and Future Trends

View full text Add to dashboard Cite

“…Subsequent studies have shown that several other solid tumor-derived cancer cells, including lung cancer and colon cancer cells, are sensitive to apoptosis induction by BA. 2,3 On the other hand, BA does not induce apoptosis in normal human cells and is nontoxic in animal studies in concentrations up to 100 mg/kg of body weight. 1,2 Therefore, BA has been considered as a promising new agent in the treatment of solid tumors.…”

mentioning

confidence: 99%

Betulinic acid, a natural cytotoxic agent, fails to trigger apoptosis in human Burkitt's lymphoma‐derived B‐cell lines

Karpova

Sanmun

Henter

et al. 2005

Intl Journal of Cancer

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Betulinic acid (BA), a pentacyclic triterpene of natural origin, effectively induces apoptosis in neuroectodermal tumors and was recently shown to be a potent trigger of cell death in human leukemia-derived cell lines. To explore the potential of BA in the treatment of hematologic malignancies, we tested a panel of 10 Burkitt's lymphoma (BL)-derived B-cell lines for sensitivity to BA. The human Jurkat T leukemia cell line was included as a positive control. Our studies show that BA exerts cytotoxic effects in some of the BL cell lines tested, including DG75, a chemoresistant BL cell line. However, cell death was caspase-independent, as evidenced by a lack of protection by zVAD-fmk, a pancaspase inhibitor, and displayed signs of necrosis. Furthermore, BA-induced caspase activation was seen to a minor extent in only 1 of the 10 BL cell lines tested (Ramos, a p53-deficient cell line), but was readily detected in Jurkat cells. Together, these studies indicate that resistance to BA-induced apoptosis is a common feature of BLderived cell lines. ' 2005 Wiley-Liss, Inc.

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Platanic Acid‐Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

Ganaie

Shahid

Rashid

et al. 2021

Chemistry & Biodiversity

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A series of rationally designed platanic acid‐based compounds derived from naturally occurring betulinic acid were synthesized through a sequence of Lemieux‐Johnson oxidation and Aldol condensation reaction. All the compounds were screened for cytotoxicity against a panel of human cancer and normal cell lines using MTT assay. From the biological data, it was observed that some of these semi‐synthetic congeners exhibited potent biological profiles compared to platanic acid. One of the compounds with the p‐tolyl substitution was found to be most active in this study, and its cytotoxicity against two of the cell lines, MDA‐MB 231 and A‐549 were in tune with the standard compound, 5‐fluorouracil.

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Development of C-20 modified betulinic acid derivatives as antitumor agents

Cited by 83 publications

References 15 publications

The Potential of Triterpenoids in the Treatment of Melanoma

The Potential of Triterpenoids in the Treatment of Melanoma

Betulinic acid, a natural cytotoxic agent, fails to trigger apoptosis in human Burkitt's lymphoma‐derived B‐cell lines

Platanic Acid‐Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

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