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Glycosyl and polyalcoholic prodrugs of lonidamine
Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs 4, 7, and 25 together with their log P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after...
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| Published in: | Bioorganic & medicinal chemistry 2008-04, Vol.18 (7), p.2445-2450 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c415t-f58120d80160ab13e48eb4aa50bdc32c6c21f394d63201a095f6acd9da48f7a73 |
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| cites | cdi_FETCH-LOGICAL-c415t-f58120d80160ab13e48eb4aa50bdc32c6c21f394d63201a095f6acd9da48f7a73 |
| container_end_page | 2450 |
| container_issue | 7 |
| container_start_page | 2445 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 18 |
| creator | Giorgioni, G. Ruggieri, S. Di Stefano, A. Sozio, P. Cinque, B. Di Marzio, L. Santoni, G. Claudi, F. |
| description | Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.
Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations. |
| doi_str_mv | 10.1016/j.bmcl.2008.02.046 |
| format | article |
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4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.
Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2008.02.046</identifier><identifier>PMID: 18321702</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Absorption ; Administration, Oral ; Alcohols - chemistry ; Animals ; Anticancer ; Antineoplastic agents ; Antineoplastic Agents - blood ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacokinetics ; Biological and medical sciences ; Cell Line, Tumor ; General aspects ; Glycosides - chemistry ; Humans ; Hydrolysis ; Indazoles - blood ; Indazoles - chemical synthesis ; Indazoles - pharmacokinetics ; Lonidamine ; Medical sciences ; Models, Chemical ; Pharmacology. Drug treatments ; Polyalcoholic ; Polyhydric ; Prodrug ; Prodrugs - chemical synthesis ; Prodrugs - metabolism ; Rats ; Solubility ; Structure-Activity Relationship ; Synthesis ; Water - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2008-04, Vol.18 (7), p.2445-2450</ispartof><rights>2008 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-f58120d80160ab13e48eb4aa50bdc32c6c21f394d63201a095f6acd9da48f7a73</citedby><cites>FETCH-LOGICAL-c415t-f58120d80160ab13e48eb4aa50bdc32c6c21f394d63201a095f6acd9da48f7a73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20253561$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18321702$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Giorgioni, G.</creatorcontrib><creatorcontrib>Ruggieri, S.</creatorcontrib><creatorcontrib>Di Stefano, A.</creatorcontrib><creatorcontrib>Sozio, P.</creatorcontrib><creatorcontrib>Cinque, B.</creatorcontrib><creatorcontrib>Di Marzio, L.</creatorcontrib><creatorcontrib>Santoni, G.</creatorcontrib><creatorcontrib>Claudi, F.</creatorcontrib><title>Glycosyl and polyalcoholic prodrugs of lonidamine</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.
Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.</description><subject>Absorption</subject><subject>Administration, Oral</subject><subject>Alcohols - chemistry</subject><subject>Animals</subject><subject>Anticancer</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - blood</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacokinetics</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>General aspects</subject><subject>Glycosides - chemistry</subject><subject>Humans</subject><subject>Hydrolysis</subject><subject>Indazoles - blood</subject><subject>Indazoles - chemical synthesis</subject><subject>Indazoles - pharmacokinetics</subject><subject>Lonidamine</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Pharmacology. Drug treatments</subject><subject>Polyalcoholic</subject><subject>Polyhydric</subject><subject>Prodrug</subject><subject>Prodrugs - chemical synthesis</subject><subject>Prodrugs - metabolism</subject><subject>Rats</subject><subject>Solubility</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><subject>Water - chemistry</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LxDAQhoMouq7-AQ_Si95aJ1_dFrzIoquw4EXBW0iTVLOkzZpshf57W7boTU9zeeaddx6ELjBkGHB-s8mqRrmMABQZkAxYfoBmmOUspQz4IZpBmUNalOztBJ3GuAHADBg7Rie4oAQvgMwQXrle-di7RLY62XrXS6f8h3dWJdvgdejeY-LrxPnWatnY1pyho1q6aM6nOUevD_cvy8d0_bx6Wt6tU8Uw36U1LzABXQxFQVaYGlaYiknJodKKEpUrgmtaMp1TAlhCyetcKl1qyYp6IRd0jq73uUONz87EnWhsVMY52RrfRbEY_i1Kzv4FcUkpoWwEyR5UwccYTC22wTYy9AKDGI2KjRiNitGoACKGC8PS5ZTeVY3RvyuTwgG4mgAZlXR1kK2y8YcjQDjlOR642z1nBmlf1gQRlTWtMtoGo3ZCe_tXj28SXZM3</recordid><startdate>20080401</startdate><enddate>20080401</enddate><creator>Giorgioni, G.</creator><creator>Ruggieri, S.</creator><creator>Di Stefano, A.</creator><creator>Sozio, P.</creator><creator>Cinque, B.</creator><creator>Di Marzio, L.</creator><creator>Santoni, G.</creator><creator>Claudi, F.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080401</creationdate><title>Glycosyl and polyalcoholic prodrugs of lonidamine</title><author>Giorgioni, G. ; Ruggieri, S. ; Di Stefano, A. ; Sozio, P. ; Cinque, B. ; Di Marzio, L. ; Santoni, G. ; Claudi, F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-f58120d80160ab13e48eb4aa50bdc32c6c21f394d63201a095f6acd9da48f7a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Absorption</topic><topic>Administration, Oral</topic><topic>Alcohols - chemistry</topic><topic>Animals</topic><topic>Anticancer</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - blood</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacokinetics</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>General aspects</topic><topic>Glycosides - chemistry</topic><topic>Humans</topic><topic>Hydrolysis</topic><topic>Indazoles - blood</topic><topic>Indazoles - chemical synthesis</topic><topic>Indazoles - pharmacokinetics</topic><topic>Lonidamine</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Pharmacology. Drug treatments</topic><topic>Polyalcoholic</topic><topic>Polyhydric</topic><topic>Prodrug</topic><topic>Prodrugs - chemical synthesis</topic><topic>Prodrugs - metabolism</topic><topic>Rats</topic><topic>Solubility</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Giorgioni, G.</creatorcontrib><creatorcontrib>Ruggieri, S.</creatorcontrib><creatorcontrib>Di Stefano, A.</creatorcontrib><creatorcontrib>Sozio, P.</creatorcontrib><creatorcontrib>Cinque, B.</creatorcontrib><creatorcontrib>Di Marzio, L.</creatorcontrib><creatorcontrib>Santoni, G.</creatorcontrib><creatorcontrib>Claudi, F.</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>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Giorgioni, G.</au><au>Ruggieri, S.</au><au>Di Stefano, A.</au><au>Sozio, P.</au><au>Cinque, B.</au><au>Di Marzio, L.</au><au>Santoni, G.</au><au>Claudi, F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glycosyl and polyalcoholic prodrugs of lonidamine</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-04-01</date><risdate>2008</risdate><volume>18</volume><issue>7</issue><spage>2445</spage><epage>2450</epage><pages>2445-2450</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.
Polyhydric alcohol derivatives of the anticancer agent lonidamine (LND) have been synthesized. The increased water solubility showed by prodrugs
4,
7, and
25 together with their log
P values (2.19, 2.55, and 2.54, respectively) and chemical stability might be beneficial for prodrugs absorption after oral administration. Moreover, the new prodrugs undergo enzymatic hydrolysis in plasma and release LND demonstrating that they are promising candidates for in vivo investigations.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>18321702</pmid><doi>10.1016/j.bmcl.2008.02.046</doi><tpages>6</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2008-04, Vol.18 (7), p.2445-2450 |
| issn | 0960-894X 0968-0896 1464-3405 1464-3391 |
| language | eng |
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| source | Elsevier |
| subjects | Absorption Administration, Oral Alcohols - chemistry Animals Anticancer Antineoplastic agents Antineoplastic Agents - blood Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacokinetics Biological and medical sciences Cell Line, Tumor General aspects Glycosides - chemistry Humans Hydrolysis Indazoles - blood Indazoles - chemical synthesis Indazoles - pharmacokinetics Lonidamine Medical sciences Models, Chemical Pharmacology. Drug treatments Polyalcoholic Polyhydric Prodrug Prodrugs - chemical synthesis Prodrugs - metabolism Rats Solubility Structure-Activity Relationship Synthesis Water - chemistry |
| title | Glycosyl and polyalcoholic prodrugs of lonidamine |
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