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1.
Bioorg Khim ; 39(2): 206-11, 2013.
Article in Russian | MEDLINE | ID: mdl-23964521

ABSTRACT

The reaction of betulonic acid chloride with 4-amino-2,2,6,6-tetramethylpeperidine-1-oxyl, 3-amino-2,2,5,5-tetramethylpyrrolidine-1-oxyl and 3-aminomethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl gave corresponding triterpenoid amides. It was found that new derivatives exhibit cytotoxic activity against tumor cells CEM-13, U-937, MT-4. CCID50 value for most activity compound--N-[3-oxolup-20(29)-en-30-yl]-(2,2,6,6-tetramethylpiperidine-4-yl)-1-oxyl--was 5.7-33.1 microM.


Subject(s)
Amides/chemical synthesis , Oleanolic Acid/analogs & derivatives , Terpenes/chemical synthesis , Amides/chemistry , Amides/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Humans , Oleanolic Acid/chemical synthesis , Oleanolic Acid/chemistry , Oleanolic Acid/pharmacology , Spin Labels , Terpenes/chemistry , Terpenes/pharmacology
2.
Bioorg Khim ; 39(6): 749-52, 2013.
Article in Russian | MEDLINE | ID: mdl-25696937

ABSTRACT

Betulonic acid amides containing a nitroxyl radical moiety possess antiholestatic effects in mice. Introduction ofpiperidine nitroxide moiety into lupan core increases its hepatoprotective activity. Oral administration of piperidine nitroxide derivative in dose 50 mg/kg doesn't stimulate transplanted tumor growth and raises a lifespan of mice.


Subject(s)
Carcinoma, Lewis Lung/drug therapy , Hepatitis/drug therapy , Oleanolic Acid/analogs & derivatives , Piperidines/administration & dosage , Pyrrolidines/administration & dosage , Amides/administration & dosage , Amides/chemistry , Animals , Apoptosis/drug effects , Carcinoma, Lewis Lung/pathology , Hepatitis/pathology , Humans , Mice , Nitrogen Oxides/chemistry , Oleanolic Acid/administration & dosage , Oleanolic Acid/chemistry , Piperidines/chemistry , Pyrrolidines/chemistry
3.
Bioorg Khim ; 33(6): 624-8, 2007.
Article in Russian | MEDLINE | ID: mdl-18173125

ABSTRACT

Derivatives of the available plant triterpenes glycyrrhetic acid and betulin (betulin succinates and amides of betulonic and 18beta-glycyrrhetic acids containing fragments of long-chain amino acids and a peptide) were synthesized. The inhibitory action of these compounds on the growth of MT-4, MOLT-4, CEM. and Hep G2 tumor cells and their effect on the apoptosis of these cells were studied. It was shown that betulonic acid amides are more effective inhibitors of the tumor cell growth than the corresponding amides of glycyrrhetic acid. It was also found that betulonic acid amides containing fragments of caprylic, pelargonic, and undecanoic acids are more effective inhibitors of tumor cell growth than betulinic acid. The 17-dipeptide derivative of betulonic acid N-{N-[3-oxo-20(29)-lupen-28-oyl]-9-aminononanoyl}-3-amino-3-phenylpropionic acid exhibited the maximum inhibitory activity toward the tumor cells studied. Data on the induction of apoptosis in tumor cells by betulin derivatives at a concentration of 10 microg/ml were obtained by flow cytometry. The amides of betulonic acid proved to be the most effective inducers of apoptosis.


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Glycyrrhetinic Acid/analogs & derivatives , Terpenes/chemistry , Triterpenes/chemistry , Antineoplastic Agents/chemical synthesis , Apoptosis , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Plants
4.
Bull Exp Biol Med ; 142(1): 69-72, 2006 Jul.
Article in English, Russian | MEDLINE | ID: mdl-17369906

ABSTRACT

We studied the effects of four synthetic amides of betulonic acid containing amino acid fragments (d,l-alpha-alanine, beta-alanine, and their methyl esters) on the rate of growth and metastatic dissemination of transplantable Lewis lung carcinoma in C57Bl/6 mice. The test compounds were administered intragastrically in a single dose of 500 mg/kg. 3-[-oxo-20(29)-lupen-28-oilamino]-propionic acid suppressed primary tumor growth (by 26%) and decreased the number of lung metastases (by more than 2 times). Antitumor and antimetastatic activity of triterpenoids decreased after methylation of the amino acid fragment in betulonic acid.


Subject(s)
Antineoplastic Agents/therapeutic use , Carcinoma, Lewis Lung/drug therapy , Neoplasm Metastasis/prevention & control , Oleanolic Acid/analogs & derivatives , Alanine/chemistry , Animals , Antineoplastic Agents/chemistry , Carcinoma, Lewis Lung/pathology , Male , Mice , Mice, Inbred C57BL , Neoplasm Metastasis/pathology , Oleanolic Acid/chemistry , Oleanolic Acid/therapeutic use
5.
Vestn Ross Akad Med Nauk ; (2): 26-30, 2005.
Article in Russian | MEDLINE | ID: mdl-15776963

ABSTRACT

The purpose of the study was to investigate, in the Vero cell culture, the antiviral activity of vegetable tritrpens derivatives and ribavirin analogues against the viruses of measles, herpes simple (type 1), cytomegaloviruses and filoviruses. The toxicity and antiviral activity of compounds were determined after coloring of cells with crystal violate. Additionally, the combined action of triterpens' derivatives and ribavirin was investigated. The studied compounds showed relatively low antiviral activity, nonetheless, further research of vegetable triterpens and their derivatives as well as ribavirin analogues would be promising.


Subject(s)
Antiviral Agents/pharmacology , Cytomegalovirus/drug effects , Filoviridae/drug effects , Herpesvirus 1, Human/drug effects , Morbillivirus/drug effects , Ribavirin/pharmacology , Triterpenes/pharmacology , Animals , Chlorocebus aethiops , Colorimetry , Cytomegalovirus/growth & development , Filoviridae/growth & development , Herpesvirus 1, Human/growth & development , Humans , In Vitro Techniques , Lung/embryology , Morbillivirus/growth & development , Vero Cells
7.
Biomed Khim ; 49(1): 96-104, 2003.
Article in Russian | MEDLINE | ID: mdl-14569879

ABSTRACT

In modeling system of the initiated oxidation of methyl oleate the antioxidation activity of a series of dipeptide derivatives of betulonic and glycyrrhetic acids, natural quinones (ubiquinone, philloquinone and menadione) and the kinetic effects of their combined action with alpha-tocopherol were studied. The same extreme character of the dependence of inhibitory action on the concentration of all investigated substances was found. Combined addition of triterpenoids or quinones together with alpha-tocopherol attenuated their effect. The mechanism of intermolecular interactions of tocopherol with quinones and triterpenoids is offered. The biological importance of these effects is discussed.


Subject(s)
Antioxidants/chemistry , Dipeptides/chemistry , Oleanolic Acid/analogs & derivatives , Quinones/chemistry , Triterpenes/chemistry , alpha-Tocopherol/chemistry , Depression, Chemical , Glycyrrhetinic Acid/analogs & derivatives , Glycyrrhetinic Acid/chemistry , Kinetics , Oleanolic Acid/chemistry , Oleic Acids/chemistry , Oxidation-Reduction , Structure-Activity Relationship , Ubiquinone/chemistry , Vitamin K 1/chemistry , Vitamin K 3/chemistry
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