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Antimicrobial and Antineoplastic Activities of Agelasine Analogs Modified in the Purine 2-Position
Agelasines are 7,9‐dialkylpurinium salts found in marine sponges (Agelas sp.), which display a variety of antimicrobial and cytotoxic effects. We have synthesized simplified agelasine analogs modified in the purine 2‐position and examined their antimicrobial and anticancer activities. The compounds...
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| Published in: | Archiv der Pharmazie (Weinheim) 2011-01, Vol.344 (1), p.50-55 |
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| cited_by | cdi_FETCH-LOGICAL-c5208-6678af740efc923c6031d05aa9fe1aa1a2012f72dfdd04804f4dd0db9f3760613 |
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| cites | cdi_FETCH-LOGICAL-c5208-6678af740efc923c6031d05aa9fe1aa1a2012f72dfdd04804f4dd0db9f3760613 |
| container_end_page | 55 |
| container_issue | 1 |
| container_start_page | 50 |
| container_title | Archiv der Pharmazie (Weinheim) |
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| creator | Roggen, Heidi Charnock, Colin Burman, Robert Felth, Jenny Larsson, Rolf Bohlin, Lars Gundersen, Lise-Lotte |
| description | Agelasines are 7,9‐dialkylpurinium salts found in marine sponges (Agelas sp.), which display a variety of antimicrobial and cytotoxic effects. We have synthesized simplified agelasine analogs modified in the purine 2‐position and examined their antimicrobial and anticancer activities. The compounds were screened against Staphylococcus aureus, Escherichia coli, Mycobacterium tuberculosis, Candida krusei, and Candida albicans, protozoa causing tropical diseases (Plasmodium falciparum, Leishmania infantum, Trypanosoma cruzi, and Trypanosoma brucei), a panel of human cancer cell lines (U‐937 GTB, RPMI 8226/s, CEM/s, and ACHN) as well as VERO and/or MRC‐5 cells. The results indicate that the introduction of a methyl group in the purine 2‐position is beneficial for antimycobacterial and antiprotozoal activity, and that amino groups may enhance activity against several cancer cell lines.
Agelasine analogs modified in the purine 2‐position have been synthesized and examined for biological activities against a variety of patogenic microorganisms as well as cancer cell lines. The introduction of a methyl group in the 2‐position appears to improve antimycobacterial activity as well as antiprotozoal activity against pathogens causing severe tropical diseases. A primary or secondary amino group in the purine 2‐position may enhance activity against several cancer cell lines. |
| doi_str_mv | 10.1002/ardp.201000148 |
| format | article |
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Agelasine analogs modified in the purine 2‐position have been synthesized and examined for biological activities against a variety of patogenic microorganisms as well as cancer cell lines. The introduction of a methyl group in the 2‐position appears to improve antimycobacterial activity as well as antiprotozoal activity against pathogens causing severe tropical diseases. A primary or secondary amino group in the purine 2‐position may enhance activity against several cancer cell lines.</description><identifier>ISSN: 0365-6233</identifier><identifier>ISSN: 1521-4184</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201000148</identifier><identifier>PMID: 21213351</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Agelas ; Agelasine ; Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial activity ; Anticancer acivitity ; Antifungal activity ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antimicrobial agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiparasitic Agents - chemical synthesis ; Antiparasitic Agents - chemistry ; Antiparasitic Agents - pharmacology ; Antiprotozoal activity ; Candida albicans ; Candida krusei ; Cell Line ; Cell Line, Tumor ; Cercopithecus aethiops ; Escherichia coli ; FARMACI ; Humans ; Leishmania infantum ; Marine ; Medical research ; Mycobacterium tuberculosis ; Neoplasms - drug therapy ; Neoplasms - pathology ; PHARMACY ; Plasmodium falciparum ; Protozoa ; Purines - chemical synthesis ; Purines - chemistry ; Purines - pharmacology ; Staphylococcus aureus ; Structure-Activity Relationship ; Trypanosoma brucei ; Trypanosoma cruzi ; Vero Cells</subject><ispartof>Archiv der Pharmazie (Weinheim), 2011-01, Vol.344 (1), p.50-55</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5208-6678af740efc923c6031d05aa9fe1aa1a2012f72dfdd04804f4dd0db9f3760613</citedby><cites>FETCH-LOGICAL-c5208-6678af740efc923c6031d05aa9fe1aa1a2012f72dfdd04804f4dd0db9f3760613</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21213351$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-141123$$DView record from Swedish Publication Index$$Hfree_for_read</backlink></links><search><creatorcontrib>Roggen, Heidi</creatorcontrib><creatorcontrib>Charnock, Colin</creatorcontrib><creatorcontrib>Burman, Robert</creatorcontrib><creatorcontrib>Felth, Jenny</creatorcontrib><creatorcontrib>Larsson, Rolf</creatorcontrib><creatorcontrib>Bohlin, Lars</creatorcontrib><creatorcontrib>Gundersen, Lise-Lotte</creatorcontrib><title>Antimicrobial and Antineoplastic Activities of Agelasine Analogs Modified in the Purine 2-Position</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><description>Agelasines are 7,9‐dialkylpurinium salts found in marine sponges (Agelas sp.), which display a variety of antimicrobial and cytotoxic effects. We have synthesized simplified agelasine analogs modified in the purine 2‐position and examined their antimicrobial and anticancer activities. The compounds were screened against Staphylococcus aureus, Escherichia coli, Mycobacterium tuberculosis, Candida krusei, and Candida albicans, protozoa causing tropical diseases (Plasmodium falciparum, Leishmania infantum, Trypanosoma cruzi, and Trypanosoma brucei), a panel of human cancer cell lines (U‐937 GTB, RPMI 8226/s, CEM/s, and ACHN) as well as VERO and/or MRC‐5 cells. The results indicate that the introduction of a methyl group in the purine 2‐position is beneficial for antimycobacterial and antiprotozoal activity, and that amino groups may enhance activity against several cancer cell lines.
Agelasine analogs modified in the purine 2‐position have been synthesized and examined for biological activities against a variety of patogenic microorganisms as well as cancer cell lines. The introduction of a methyl group in the 2‐position appears to improve antimycobacterial activity as well as antiprotozoal activity against pathogens causing severe tropical diseases. A primary or secondary amino group in the purine 2‐position may enhance activity against several cancer cell lines.</description><subject>Agelas</subject><subject>Agelasine</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>Anticancer acivitity</subject><subject>Antifungal activity</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiparasitic Agents - chemical synthesis</subject><subject>Antiparasitic Agents - chemistry</subject><subject>Antiparasitic Agents - pharmacology</subject><subject>Antiprotozoal activity</subject><subject>Candida albicans</subject><subject>Candida krusei</subject><subject>Cell Line</subject><subject>Cell Line, Tumor</subject><subject>Cercopithecus aethiops</subject><subject>Escherichia coli</subject><subject>FARMACI</subject><subject>Humans</subject><subject>Leishmania infantum</subject><subject>Marine</subject><subject>Medical research</subject><subject>Mycobacterium tuberculosis</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - pathology</subject><subject>PHARMACY</subject><subject>Plasmodium falciparum</subject><subject>Protozoa</subject><subject>Purines - chemical synthesis</subject><subject>Purines - chemistry</subject><subject>Purines - pharmacology</subject><subject>Staphylococcus aureus</subject><subject>Structure-Activity Relationship</subject><subject>Trypanosoma brucei</subject><subject>Trypanosoma cruzi</subject><subject>Vero Cells</subject><issn>0365-6233</issn><issn>1521-4184</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkctv1DAQxi1ERZeFK0cUiUM5kMXPPI5RSxekbVnxqsTFcmJ7ccnGwU4o_e-ZKO0KcYCTR57ffJr5PoSeEbwiGNPXKuh-RTHUmPDiAVoQQUnKScEfogVmmUgzytgxehzjNTAMU_EIHVNCCWOCLFBddYPbuyb42qk2UZ1Opp_O-L5VcXBNUjWD--kGZ2LibVLtDPxDHzDV-l1MLrx21hmduC4ZvplkO4apTdOtjzDmuyfoyKo2mqd37xJ9Pn_z6fRtunm_fndabdJGUFykWZYXyuYcG9uUlDUZZkRjoVRpDVGKKLiS2pxqqzXmBeaWQ6Hr0rI8wxlhS_Rq1o03ph9r2Qe3V-FWeuXkmftSSR92chwl4YSAJ0t0MuN98D9GEwe5d7Exbavg-DHKgtISM3AKyJf_JAkjIsOlwJPoi7_Qaz8GcAoowXmRw94cqNVMge0xBmMPuxIsp1jlFKs8xAoDz-9kx3pv9AG_zxGAcgZuXGtu_yMnqw9n2z_F03nWxcH8Osyq8F1mOcuFvLpcy3X5dXO-KT_KK_YbG7q8nw</recordid><startdate>201101</startdate><enddate>201101</enddate><creator>Roggen, Heidi</creator><creator>Charnock, Colin</creator><creator>Burman, Robert</creator><creator>Felth, Jenny</creator><creator>Larsson, Rolf</creator><creator>Bohlin, Lars</creator><creator>Gundersen, Lise-Lotte</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7QL</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H97</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>ADTPV</scope><scope>AOWAS</scope><scope>DF2</scope></search><sort><creationdate>201101</creationdate><title>Antimicrobial and Antineoplastic Activities of Agelasine Analogs Modified in the Purine 2-Position</title><author>Roggen, Heidi ; 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Pharm. Pharm. Med. Chem</addtitle><date>2011-01</date><risdate>2011</risdate><volume>344</volume><issue>1</issue><spage>50</spage><epage>55</epage><pages>50-55</pages><issn>0365-6233</issn><issn>1521-4184</issn><eissn>1521-4184</eissn><abstract>Agelasines are 7,9‐dialkylpurinium salts found in marine sponges (Agelas sp.), which display a variety of antimicrobial and cytotoxic effects. We have synthesized simplified agelasine analogs modified in the purine 2‐position and examined their antimicrobial and anticancer activities. The compounds were screened against Staphylococcus aureus, Escherichia coli, Mycobacterium tuberculosis, Candida krusei, and Candida albicans, protozoa causing tropical diseases (Plasmodium falciparum, Leishmania infantum, Trypanosoma cruzi, and Trypanosoma brucei), a panel of human cancer cell lines (U‐937 GTB, RPMI 8226/s, CEM/s, and ACHN) as well as VERO and/or MRC‐5 cells. The results indicate that the introduction of a methyl group in the purine 2‐position is beneficial for antimycobacterial and antiprotozoal activity, and that amino groups may enhance activity against several cancer cell lines.
Agelasine analogs modified in the purine 2‐position have been synthesized and examined for biological activities against a variety of patogenic microorganisms as well as cancer cell lines. The introduction of a methyl group in the 2‐position appears to improve antimycobacterial activity as well as antiprotozoal activity against pathogens causing severe tropical diseases. A primary or secondary amino group in the purine 2‐position may enhance activity against several cancer cell lines.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21213351</pmid><doi>10.1002/ardp.201000148</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_swepub_primary_oai_DiVA_org_uu_141123 |
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| subjects | Agelas Agelasine Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial activity Anticancer acivitity Antifungal activity Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antimicrobial agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiparasitic Agents - chemical synthesis Antiparasitic Agents - chemistry Antiparasitic Agents - pharmacology Antiprotozoal activity Candida albicans Candida krusei Cell Line Cell Line, Tumor Cercopithecus aethiops Escherichia coli FARMACI Humans Leishmania infantum Marine Medical research Mycobacterium tuberculosis Neoplasms - drug therapy Neoplasms - pathology PHARMACY Plasmodium falciparum Protozoa Purines - chemical synthesis Purines - chemistry Purines - pharmacology Staphylococcus aureus Structure-Activity Relationship Trypanosoma brucei Trypanosoma cruzi Vero Cells |
| title | Antimicrobial and Antineoplastic Activities of Agelasine Analogs Modified in the Purine 2-Position |
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