Tumor-specificity and Type of Cell Death Induced by Vitamin K2 Derivatives and Prenylalcohols
Fourteen vitamin K 2 (menaquinone (MK)-n, n=1~14) and ten prenylalcohol derivatives (n=1~10) with different numbers (n) of isoprenyl groups in the side chains were investigated for their cytotoxicity against nine human tumor cell lines and three human normal oral cells. Among the vitamin K 2 derivat...
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| Veröffentlicht in: | Anticancer research 2008-01, Vol.28 (1A), p.151-158 |
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| creator | SAKAGAMI, Hiroshi HASHIMOTO, Ken SUZUKI, Fumika ISHIHARA, Mariko KIKUCHI, Hirotaka KATAYAMA, Tadashi SATOH, Kazue |
| description | Fourteen vitamin K 2 (menaquinone (MK)-n, n=1~14) and ten prenylalcohol derivatives (n=1~10) with different numbers (n) of isoprenyl groups in
the side chains were investigated for their cytotoxicity against nine human tumor cell lines and three human normal oral cells.
Among the vitamin K 2 derivatives, MK-2 (n=2) showed the greatest cytotoxicity, followed by MK-1 (n=1) and MK-3 (n=3). MK-1, MK-2 and MK-3 showed
the highest tumor-specific index (TS= >2.0, 2.0 and >1.7, respectively). Among the prenylalcohols, geranylgeraniol (GG) (n=4)
showed the highest cytotoxicity, followed by farnesol (n=3) and geranylfarnesol (GF) (n=3). GG showed the highest tumor-specificity
(TS=1.8), followed by farnesol (TS=>1.4), GF (TS=> |
| format | Article |
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the side chains were investigated for their cytotoxicity against nine human tumor cell lines and three human normal oral cells.
Among the vitamin K 2 derivatives, MK-2 (n=2) showed the greatest cytotoxicity, followed by MK-1 (n=1) and MK-3 (n=3). MK-1, MK-2 and MK-3 showed
the highest tumor-specific index (TS= >2.0, 2.0 and >1.7, respectively). Among the prenylalcohols, geranylgeraniol (GG) (n=4)
showed the highest cytotoxicity, followed by farnesol (n=3) and geranylfarnesol (GF) (n=3). GG showed the highest tumor-specificity
(TS=1.8), followed by farnesol (TS=>1.4), GF (TS=> <1.3). However, the tumor-specificity of MK-2 and GG was much lower than
that of conventional chemotherapeutic agents. The human leukemic cell lines were the most sensitive, whereas the human glioblastoma
cell lines were the most resistant to MK-2 and GG. MK-2 did not induce internucleosomal DNA fragmentation in either the human
promyelocytic leukemia HL-60 or the human squamous cell carcinoma HSC-4 cell lines. GG induced marginal internucleosomal DNA
fragmentation in the HL-60 cells, but not in the HSC-4 cells. Both MK-2 and GG did not induce the formation of autophagosomes,
nor did they clearly change the intracellular concentration of three polyamines. Electron spin resonance (ESR) spectroscopy
showed that only MK-1 (n=1), as well as GGF (n=7) and GFF (n=8) which had lower cytotoxicity, produced radicals, suggesting
the lack of connection between cytotoxicity and radical production. The present study demonstrates that the presence of 1,4-naphtoquinone
structure (including α,β-unsaturated ketones) in vitamin K 2 derivatives confers on them the ability to induce non-apoptotic cell death.</description><identifier>ISSN: 0250-7005</identifier><identifier>EISSN: 1791-7530</identifier><identifier>PMID: 18383839</identifier><language>eng</language><publisher>Attiki: International Institute of Anticancer Research</publisher><subject>Biogenic Polyamines - metabolism ; Biological and medical sciences ; Cell Death - drug effects ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; HL-60 Cells ; Humans ; K562 Cells ; Medical sciences ; Neoplasms - drug therapy ; Neoplasms - metabolism ; Neoplasms - pathology ; Pentanols - pharmacology ; Tumors ; Vitamin K 2 - analogs & derivatives ; Vitamin K 2 - pharmacology ; Vitamins - pharmacology</subject><ispartof>Anticancer research, 2008-01, Vol.28 (1A), p.151-158</ispartof><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20165809$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18383839$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SAKAGAMI, Hiroshi</creatorcontrib><creatorcontrib>HASHIMOTO, Ken</creatorcontrib><creatorcontrib>SUZUKI, Fumika</creatorcontrib><creatorcontrib>ISHIHARA, Mariko</creatorcontrib><creatorcontrib>KIKUCHI, Hirotaka</creatorcontrib><creatorcontrib>KATAYAMA, Tadashi</creatorcontrib><creatorcontrib>SATOH, Kazue</creatorcontrib><title>Tumor-specificity and Type of Cell Death Induced by Vitamin K2 Derivatives and Prenylalcohols</title><title>Anticancer research</title><addtitle>Anticancer Res</addtitle><description>Fourteen vitamin K 2 (menaquinone (MK)-n, n=1~14) and ten prenylalcohol derivatives (n=1~10) with different numbers (n) of isoprenyl groups in
the side chains were investigated for their cytotoxicity against nine human tumor cell lines and three human normal oral cells.
Among the vitamin K 2 derivatives, MK-2 (n=2) showed the greatest cytotoxicity, followed by MK-1 (n=1) and MK-3 (n=3). MK-1, MK-2 and MK-3 showed
the highest tumor-specific index (TS= >2.0, 2.0 and >1.7, respectively). Among the prenylalcohols, geranylgeraniol (GG) (n=4)
showed the highest cytotoxicity, followed by farnesol (n=3) and geranylfarnesol (GF) (n=3). GG showed the highest tumor-specificity
(TS=1.8), followed by farnesol (TS=>1.4), GF (TS=> <1.3). However, the tumor-specificity of MK-2 and GG was much lower than
that of conventional chemotherapeutic agents. The human leukemic cell lines were the most sensitive, whereas the human glioblastoma
cell lines were the most resistant to MK-2 and GG. MK-2 did not induce internucleosomal DNA fragmentation in either the human
promyelocytic leukemia HL-60 or the human squamous cell carcinoma HSC-4 cell lines. GG induced marginal internucleosomal DNA
fragmentation in the HL-60 cells, but not in the HSC-4 cells. Both MK-2 and GG did not induce the formation of autophagosomes,
nor did they clearly change the intracellular concentration of three polyamines. Electron spin resonance (ESR) spectroscopy
showed that only MK-1 (n=1), as well as GGF (n=7) and GFF (n=8) which had lower cytotoxicity, produced radicals, suggesting
the lack of connection between cytotoxicity and radical production. The present study demonstrates that the presence of 1,4-naphtoquinone
structure (including α,β-unsaturated ketones) in vitamin K 2 derivatives confers on them the ability to induce non-apoptotic cell death.</description><subject>Biogenic Polyamines - metabolism</subject><subject>Biological and medical sciences</subject><subject>Cell Death - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>K562 Cells</subject><subject>Medical sciences</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - metabolism</subject><subject>Neoplasms - pathology</subject><subject>Pentanols - pharmacology</subject><subject>Tumors</subject><subject>Vitamin K 2 - analogs & derivatives</subject><subject>Vitamin K 2 - pharmacology</subject><subject>Vitamins - pharmacology</subject><issn>0250-7005</issn><issn>1791-7530</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpN0E1PwzAMBuAKgdgY_AWUC9wq5aNJuuM0viaQ4DC4ochNExqUtiNph_rv6WAg5IMPfvzK8kEyJXJOUskZPkymmHKcSoz5JDmJ8R1jIeY5O04mJGe7mk-T13VftyGNG6Odddp1A4KmROthY1Br0dJ4j64MdBVaNWWvTYmKAb24DmrXoHs6zoLbQue2Jn4vPgXTDB68bqvWx9PkyIKP5mzfZ8nzzfV6eZc-PN6ulouHtCJ51qUZsYJSMEYLkVnJOJU8JwVkFqwmBLISCkmlzVlpOSVYYFGMvjS4wJJmmM2Sy5_cTWg_ehM7Vbuox9uhMW0flcQZl5jt4Pke9kVtSrUJroYwqN-HjOBiDyBq8DZAo138cxQTwXP8z1Xurfp0wahYg_djLFMQaK7IQhFO2BfPfnaS</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>SAKAGAMI, Hiroshi</creator><creator>HASHIMOTO, Ken</creator><creator>SUZUKI, Fumika</creator><creator>ISHIHARA, Mariko</creator><creator>KIKUCHI, Hirotaka</creator><creator>KATAYAMA, Tadashi</creator><creator>SATOH, Kazue</creator><general>International Institute of Anticancer Research</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20080101</creationdate><title>Tumor-specificity and Type of Cell Death Induced by Vitamin K2 Derivatives and Prenylalcohols</title><author>SAKAGAMI, Hiroshi ; HASHIMOTO, Ken ; SUZUKI, Fumika ; ISHIHARA, Mariko ; KIKUCHI, Hirotaka ; KATAYAMA, Tadashi ; SATOH, Kazue</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-h184t-41f622aeec664f73527581ba4fafc11a4dab727f83df5210606b22ade0b072403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Biogenic Polyamines - metabolism</topic><topic>Biological and medical sciences</topic><topic>Cell Death - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>K562 Cells</topic><topic>Medical sciences</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - metabolism</topic><topic>Neoplasms - pathology</topic><topic>Pentanols - pharmacology</topic><topic>Tumors</topic><topic>Vitamin K 2 - analogs & derivatives</topic><topic>Vitamin K 2 - pharmacology</topic><topic>Vitamins - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SAKAGAMI, Hiroshi</creatorcontrib><creatorcontrib>HASHIMOTO, Ken</creatorcontrib><creatorcontrib>SUZUKI, Fumika</creatorcontrib><creatorcontrib>ISHIHARA, Mariko</creatorcontrib><creatorcontrib>KIKUCHI, Hirotaka</creatorcontrib><creatorcontrib>KATAYAMA, Tadashi</creatorcontrib><creatorcontrib>SATOH, Kazue</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Anticancer research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SAKAGAMI, Hiroshi</au><au>HASHIMOTO, Ken</au><au>SUZUKI, Fumika</au><au>ISHIHARA, Mariko</au><au>KIKUCHI, Hirotaka</au><au>KATAYAMA, Tadashi</au><au>SATOH, Kazue</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tumor-specificity and Type of Cell Death Induced by Vitamin K2 Derivatives and Prenylalcohols</atitle><jtitle>Anticancer research</jtitle><addtitle>Anticancer Res</addtitle><date>2008-01-01</date><risdate>2008</risdate><volume>28</volume><issue>1A</issue><spage>151</spage><epage>158</epage><pages>151-158</pages><issn>0250-7005</issn><eissn>1791-7530</eissn><abstract>Fourteen vitamin K 2 (menaquinone (MK)-n, n=1~14) and ten prenylalcohol derivatives (n=1~10) with different numbers (n) of isoprenyl groups in
the side chains were investigated for their cytotoxicity against nine human tumor cell lines and three human normal oral cells.
Among the vitamin K 2 derivatives, MK-2 (n=2) showed the greatest cytotoxicity, followed by MK-1 (n=1) and MK-3 (n=3). MK-1, MK-2 and MK-3 showed
the highest tumor-specific index (TS= >2.0, 2.0 and >1.7, respectively). Among the prenylalcohols, geranylgeraniol (GG) (n=4)
showed the highest cytotoxicity, followed by farnesol (n=3) and geranylfarnesol (GF) (n=3). GG showed the highest tumor-specificity
(TS=1.8), followed by farnesol (TS=>1.4), GF (TS=> <1.3). However, the tumor-specificity of MK-2 and GG was much lower than
that of conventional chemotherapeutic agents. The human leukemic cell lines were the most sensitive, whereas the human glioblastoma
cell lines were the most resistant to MK-2 and GG. MK-2 did not induce internucleosomal DNA fragmentation in either the human
promyelocytic leukemia HL-60 or the human squamous cell carcinoma HSC-4 cell lines. GG induced marginal internucleosomal DNA
fragmentation in the HL-60 cells, but not in the HSC-4 cells. Both MK-2 and GG did not induce the formation of autophagosomes,
nor did they clearly change the intracellular concentration of three polyamines. Electron spin resonance (ESR) spectroscopy
showed that only MK-1 (n=1), as well as GGF (n=7) and GFF (n=8) which had lower cytotoxicity, produced radicals, suggesting
the lack of connection between cytotoxicity and radical production. The present study demonstrates that the presence of 1,4-naphtoquinone
structure (including α,β-unsaturated ketones) in vitamin K 2 derivatives confers on them the ability to induce non-apoptotic cell death.</abstract><cop>Attiki</cop><pub>International Institute of Anticancer Research</pub><pmid>18383839</pmid><tpages>8</tpages></addata></record> |
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| subjects | Biogenic Polyamines - metabolism Biological and medical sciences Cell Death - drug effects Cell Line, Tumor Drug Screening Assays, Antitumor HL-60 Cells Humans K562 Cells Medical sciences Neoplasms - drug therapy Neoplasms - metabolism Neoplasms - pathology Pentanols - pharmacology Tumors Vitamin K 2 - analogs & derivatives Vitamin K 2 - pharmacology Vitamins - pharmacology |
| title | Tumor-specificity and Type of Cell Death Induced by Vitamin K2 Derivatives and Prenylalcohols |
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