Mitochondrial targeting derivatives of honokiol enhanced selective antitumor activity in NCI-H446 cells and decreased in vivo toxicity in Caenorhabditis elegans
Mitochondria, responsible for ATP production and apoptosis regulation, play a key role in cancer cells. Honokiol regulates apoptosis through the endogenous mitochondrial pathway but does not specifically target tumor cells. We designed 28 novel derivatives of honokiol using triple-function delocaliz...
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| Published in | European journal of medicinal chemistry Vol. 264; p. 115996 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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ISSY-LES-MOULINEAUX
Elsevier
15.01.2024
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| Abstract | Mitochondria, responsible for ATP production and apoptosis regulation, play a key role in cancer cells. Honokiol regulates apoptosis through the endogenous mitochondrial pathway but does not specifically target tumor cells. We designed 28 novel derivatives of honokiol using triple-function delocalized lipophilic cations such as berberine and F16 as mitochondrion-targeting carriers. While all derivatives exhibited enhanced cytotoxicity toward tumor cells compared to honokiol, the derivative 2E-3-F16 exhibited a substantial tumor cell selectivity between NCI-H446 cancer cells and HBE cells by one order of magnitude and enhanced the sensitivity of A549 cells to cisplatin. Mechanistically, it targeted mitochondria and induced apoptosis by preventing tumor cells from entering the G0/G1 phases as well as inducing an abnormal elevation of reactive oxygen species, thereby decreasing the mitochondrial membrane potential level. It also showed lower toxicity toward Caenorhabditis elegans than honokiol. This study provides a possible method for developing mitochondrion-targeting antitumor drugs with high efficiency and low toxicity based on natural products. |
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| AbstractList | Mitochondria, responsible for ATP production and apoptosis regulation, play a key role in cancer cells. Honokiol regulates apoptosis through the endogenous mitochondrial pathway but does not specifically target tumor cells. We designed 28 novel derivatives of honokiol using triple-function delocalized lipophilic cations such as berberine and F16 as mitochondrion-targeting carriers. While all derivatives exhibited enhanced cytotoxicity toward tumor cells compared to honokiol, the derivative 2E-3-F16 exhibited a substantial tumor cell selectivity between NCI-H446 cancer cells and HBE cells by one order of magnitude and enhanced the sensitivity of A549 cells to cisplatin. Mechanistically, it targeted mitochondria and induced apoptosis by preventing tumor cells from entering the G0/G1 phases as well as inducing an abnormal elevation of reactive oxygen species, thereby decreasing the mitochondrial membrane potential level. It also showed lower toxicity toward Caenorhabditis elegans than honokiol. This study provides a possible method for developing mitochondrion-targeting antitumor drugs with high efficiency and low toxicity based on natural products. Mitochondria, responsible for ATP production and apoptosis regulation, play a key role in cancer cells. Honokiol regulates apoptosis through the endogenous mitochondrial pathway but does not specifically target tumor cells. We designed 28 novel derivatives of honokiol using triple-function delocalized lipophilic cations such as berberine and F16 as mitochondrion-targeting carriers. While all derivatives exhibited enhanced cytotoxicity toward tumor cells compared to honokiol, the derivative 2E-3-F16 exhibited a substantial tumor cell selectivity between NCI-H446 cancer cells and HBE cells by one order of magnitude and enhanced the sensitivity of A549 cells to cisplatin. Mechanistically, it targeted mitochondria and induced apoptosis by preventing tumor cells from entering the G0/G1 phases as well as inducing an abnormal elevation of reactive oxygen species, thereby decreasing the mitochondrial membrane potential level. It also showed lower toxicity toward Caenorhabditis elegans than honokiol. This study provides a possible method for developing mitochondrion-targeting antitumor drugs with high efficiency and low toxicity based on natural products. |
| ArticleNumber | 115996 |
| Author | Lou, Hongxiang Cui, Wenbo Zhang, Yue Fan, Peihong Zhang, Jiaozhen Miao, Huicong Zhang, Tao |
| Author_xml | – sequence: 1 givenname: Huicong surname: Miao fullname: Miao, Huicong organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China – sequence: 2 givenname: Wenbo surname: Cui fullname: Cui, Wenbo organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China – sequence: 3 givenname: Tao surname: Zhang fullname: Zhang, Tao organization: Shandong Qidu Pharmaceut Res Inst, Shandong Prov Key Lab Neuroprotect Drugs, Zibo 255400, Peoples R China – sequence: 4 givenname: Yue surname: Zhang fullname: Zhang, Yue organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China – sequence: 5 givenname: Jiaozhen surname: Zhang fullname: Zhang, Jiaozhen organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China – sequence: 6 givenname: Hongxiang surname: Lou fullname: Lou, Hongxiang email: louhongxiang@sdu.edu.cn organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China – sequence: 7 givenname: Peihong surname: Fan fullname: Fan, Peihong email: fanpeihong@sdu.edu.cn organization: Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Dept Nat Prod Chem,Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38086195$$D View this record in MEDLINE/PubMed |
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| Keywords | Mitochondria targeting METABOLITES TISSUE Honokiol F16 MECHANISMS FLAVONOIDS SAPONINS TRIGONELLA-FOENUM-GRAECUM ANTIOXIDANT Antitumor DLCs FENUGREEK SEEDS CHLOROPHYLL CONSTITUENTS |
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| Title | Mitochondrial targeting derivatives of honokiol enhanced selective antitumor activity in NCI-H446 cells and decreased in vivo toxicity in Caenorhabditis elegans |
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