Synthesis and studies of anticancer properties of lupane-type triterpenoid derivatives containing a cisplatin fragment

Emmerich, Daniel J.; Vanchanagiri, Kranthi; Baratto, Leopoldo Clemente; Schmidt, Harry; Paschke, Ralf

doi:10.1016/j.ejmech.2014.01.031

Cited by 30 publications

(19 citation statements)

References 21 publications

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“…Similarly, viability of normal fibroblast was even more affected by BA and BATRIS in comparison to cancer cells. This data opposed to previously observed high selectivity of BA for cancer cells [32] and definitely require further confirmation in diverse types of normal cells. Conjugate BATRISPt was found to be less toxic to primary cells in comparison to maternal drugs.…”

Section: Cytotoxicity Of Batrisptcontrasting

confidence: 99%

“…The obtained data showed that decreased efficacy of conjugate compound BATRISPt might be caused by the activation of some cytoprotective mechanism inside of the cell, which in final point neutralizes the toxicity of the treatment. Data presented herein are in concordance with recently reported results, where different betulinic acid derivatives conjugated with PtCl2-fragment were tested [32]. However, strong selectivity of some of these synthetic compounds apart from lower cytotoxicity indicated that they might have potential as anticancer agents.…”

Section: Mechanism Of Actionsupporting

confidence: 92%

“…[25,26]. However, investigations on betulinic acid in the last few years have been pointed toward the field of antitumor properties [27][28][29][30][31].We recently reported the synthesis and characterization of the new series of betulinic acid-cisplatin conjugates, which are both apoptosis inducing agents [32]. However, their cytotoxicity was found to be lower than parental drugs cisplatin and betulinic acid.…”

mentioning

confidence: 99%

“…We recently reported the synthesis and characterization of the new series of betulinic acid-cisplatin conjugates, which are both apoptosis inducing agents [32]. However, their cytotoxicity was found to be lower than parental drugs cisplatin and betulinic acid.…”

mentioning

confidence: 99%

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(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity

et al. 2017

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Synthesis of platinum(II) conjugate with acetylated betulinic acid tris(hydroxymethyl) aminomethane ester (BATRIS) is presented (BATRISPt). HR-ESI-MS and multinuclear NMR spectroscopy, as well as elemental analysis were used for characterization of BATRISPt. Cytotoxicity (3-(4,5-dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), crystal violet (CV), and sulforhodamine B (SRB) assays) of BA, BATRIS, BATRISPt, and cisplatin were assessed on seven different tumor cell lines: melanoma B16, colon HCT116 and DLD-1, adenocarcinoma HeLa, breast MCF-7, and anaplastic thyroid tumor 8505C and SW1736; as well as normal MRC-5 fibroblasts. Furthermore, the effect of the mentioned compounds on the apoptosis (Annexin V/PI assay) and autophagy induction (acridine orange (AO) assay) as well as caspase 3, 8, and 9 activation were investigated on the selected B16 melanoma cell line. BATRISPt showed lower activity than BA, BATRIS, or cisplatin. All tested compounds triggered apoptosis in B16 cells. Induction of autophagy was observed in B16 cells exposed only to BATRIS. On the other hand, new conjugate activates caspases 8 and 9 in B16 cells with higher impact than BATRIS or cisplatin alone.Inorganics 2017, 5, 56 2 of 13 instance, how such compounds can be delivered, metabolized, and how and to which magnitude they may enter the tumor cells. On the other side, two components covalently linked to each other-double drug [13], presumably-may possess different behavior than single components alone.Even lower in activity than paclitaxel or doxorubicin [14,15], a cell-type-specific antitumor active compound betulinic acid (BA) has drawn more attention in the last few years and is still explored by many groups [16][17][18][19][20][21][22][23][24]. BA is a naturally occurring pentacyclic triterpenoid which is isolated from the bark of several species of plants (e.g., white birch). Betulinic acid and its derivatives present compounds with numerous biological activities-for instance, antioxidant, antiviral, antimicrobial, anti-inflammatory, antidiabetic, immunomodulatory, etc. [25,26]. However, investigations on betulinic acid in the last few years have been pointed toward the field of antitumor properties [27][28][29][30][31].We recently reported the synthesis and characterization of the new series of betulinic acid-cisplatin conjugates, which are both apoptosis inducing agents [32]. However, their cytotoxicity was found to be lower than parental drugs cisplatin and betulinic acid. Herein we report on the synthesis, characterization, and in vitro activity of acetylated betulinic acid derivative tris(hydroxymethyl)aminomethane (TRIS) ester conjugated with PtCl 3 -fragment.

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Section: Cytotoxicity Of Batrisptcontrasting

confidence: 99%

Section: Mechanism Of Actionsupporting

confidence: 92%

mentioning

confidence: 99%

mentioning

confidence: 99%

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(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity

et al. 2017

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“…The water-soluble derivative NVX-207 revealed high activity in dogs suffering from persistent pre-treated tumors (Willmann, 2009). Platinum complexes might be promising in conjugation with betulinic acid concerning the treatment of certain resistant cancer types (Emmerich, 2014).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of (6-aminomethylnicotinate)Dichloridoplatinum(II) Conjugates with Lupane-Type Triterpenes

Effenberger-Neidnicht¹,

Schobert²,

Biersack³

2014

j pharmaceut sci pharmacol

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6-aminomethylnicotinate)Pt(II) complexes of betulin and betulinic acid derivatives were prepared, characterized and tested for growth inhibitory activity in different human tumor cell lines. While the tumor selective character of betulinic acid was conserved, two Pt(II) complexes (5a, 5b) surpassed the activity of betulinic acid (1a) or cisplatin in multi-drug resistant KB-V1/Vbl cervix carcinoma cells. Complex 5a also displayed stronger activity than betulinic acid in HL-60 leukemia cells. All platinum conjugates 5a-c were highly tumor selective and showed no toxicity in non-malignant fibroblast cells.

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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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Synthesis and studies of anticancer properties of lupane-type triterpenoid derivatives containing a cisplatin fragment

Cited by 30 publications

References 21 publications

(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity

(18-Crown-6)potassium(I) Trichlorido[28-acetyl-3-(tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and In Vitro Antitumor Activity

Synthesis and Anticancer Activity of (6-aminomethylnicotinate)Dichloridoplatinum(II) Conjugates with Lupane-Type Triterpenes

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

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