The synthesis of 18β-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells

18β-Glycyrrhetinic acid (GA), 3β-hydroxyl-11-oxo-olean-12-ene-29-oic acid, has been found to inhibit growth and to induce apoptosis in cancer cells. Through structural modification, 16 GA derivatives (12 novel compounds) with modified structures at the C 3 and C 29 positions were synthesized. The an...

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Published inBioorganic & medicinal chemistry Vol. 15; no. 16; pp. 5432 - 5439
Main Authors Liu, Dan, Song, Dandan, Guo, Gang, Wang, Rui, Lv, Jinling, Jing, Yongkui, Zhao, Linxiang
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 15.08.2007
Elsevier Science
Subjects
18β-Glycyrrhetinic acid
Antineoplastic agents
Apoptosis
Biological and medical sciences
General aspects
Medical sciences
Pharmacology. Drug treatments
Structure–activity relationship
Synthesis
18β-Glycyrrhetinic acid
Synthesis
Structure–activity relationship
Apoptosis
Antineoplastic agent
Human
Terpenoid
Growth
Leukemia
Oxime
Malignant hemopathy
Enoxolone
In vitro
HL60 cell line
Dose activity relation
Oleanane derivatives
Cell line
Structure activity relation
Structure- activity relationship
Triterpene
Inhibition
Chemical synthesis
Tumor cell
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Abstract 18β-Glycyrrhetinic acid (GA), 3β-hydroxyl-11-oxo-olean-12-ene-29-oic acid, has been found to inhibit growth and to induce apoptosis in cancer cells. Through structural modification, 16 GA derivatives (12 novel compounds) with modified structures at the C 3 and C 29 positions were synthesized. The antiproliferative effects and apoptosis induction abilities of these compounds were determined in human leukemia HL-60 cells. The replacement of the hydroxyl group of GA with a carbonyl group or an oxime group at C 3 position does not influence the antiproliferative effect. However, the antiproliferative and apoptosis induction abilities of the compounds with a replaced alkoxyimino group at position C 3 and a free C 29 carboxyl group are markedly increased.
AbstractList 18β-Glycyrrhetinic acid (GA), 3β-hydroxyl-11-oxo-olean-12-ene-29-oic acid, has been found to inhibit growth and to induce apoptosis in cancer cells. Through structural modification, 16 GA derivatives (12 novel compounds) with modified structures at the C 3 and C 29 positions were synthesized. The antiproliferative effects and apoptosis induction abilities of these compounds were determined in human leukemia HL-60 cells. The replacement of the hydroxyl group of GA with a carbonyl group or an oxime group at C 3 position does not influence the antiproliferative effect. However, the antiproliferative and apoptosis induction abilities of the compounds with a replaced alkoxyimino group at position C 3 and a free C 29 carboxyl group are markedly increased.
Author Song, Dandan
Lv, Jinling
Guo, Gang
Zhao, Linxiang
Jing, Yongkui
Liu, Dan
Wang, Rui
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  organization: Shenyang Pharmaceutical University, Shenyang 110016, PR China
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  givenname: Linxiang
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  fullname: Zhao, Linxiang
  email: linxiang.zhao@vip.sina.com
  organization: Shenyang Pharmaceutical University, Shenyang 110016, PR China
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10.1021/jo00376a046
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10.1016/S0040-4039(01)84734-1
10.1007/BF00272743
10.1055/s-1972-21955
10.1039/JR9650006655
10.1248/cpb.48.1681
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Issue 16
Keywords 18β-Glycyrrhetinic acid
Synthesis
Structure–activity relationship
Apoptosis
Antineoplastic agent
Human
Terpenoid
Growth
Leukemia
Oxime
Malignant hemopathy
Enoxolone
In vitro
HL60 cell line
Dose activity relation
Oleanane derivatives
Cell line
Structure activity relation
Structure- activity relationship
Triterpene
Inhibition
Chemical synthesis
Tumor cell
Language English
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Snippet 18β-Glycyrrhetinic acid (GA), 3β-hydroxyl-11-oxo-olean-12-ene-29-oic acid, has been found to inhibit growth and to induce apoptosis in cancer cells. Through...
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StartPage 5432
SubjectTerms 18β-Glycyrrhetinic acid
Antineoplastic agents
Apoptosis
Biological and medical sciences
General aspects
Medical sciences
Pharmacology. Drug treatments
Structure–activity relationship
Synthesis
Title The synthesis of 18β-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells
URI https://dx.doi.org/10.1016/j.bmc.2007.05.057
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