title: Synthesis of Bioconjugate Sesterterpenoids with Phospholipids and Polyunsaturated Fatty Acids.
abstract: A series of sesterterpenoid bioconjugates with phospholipids and polyunsaturated fatty acids (PUFAs) have been synthesized for biological activity testing as antiproliferative agents in several cancer cell lines. Different substitution analogues of the original lipidic ether edelfosine (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine) are obtained varying the sesterterpenoid in position 1 or 2 of the glycerol or a phosphocholine or PUFA unit in position 3. Simple bioconjugates of sesterterpenoids and eicosapentaenoic acid (EPA) have been obtained too. All synthetic derivatives were tested against the human tumour cell lines HeLa (cervix) and MCF-7 (breast). Some compounds showed good IC50 (0.3 and 0.2 μM) values against these cell lines.
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. anagm@usal.es.
authors.forename: Ana
authors.initials: A
authors.lastname: Gil-Mesón
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. alexmaron@usal.es.
authors.forename: Alejandro M
authors.initials: AM
authors.lastname: Roncero
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. ignaciotobal@usal.es.
authors.forename: Ignacio E
authors.initials: IE
authors.lastname: Tobal
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. pbb@usal.es.
authors.forename: Pilar
authors.initials: P
authors.lastname: Basabe
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. ddm@usal.es.
authors.forename: David
authors.initials: D
authors.lastname: Díez
authors.affiliation: Instituto de Biología Molecular y Celular del Cáncer, Centro de Investigación del Cáncer, CSIC-Universidad de Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain. fmollin@usal.es.|Laboratory of Cell Death and Cancer Therapy, Department of Cellular and Molecular Medicine, Centro de Investigaciones Biológicas, CSIC, C/Ramiro de Maeztu 9, 28040 Madrid, Spain. fmollin@usal.es.
authors.forename: Faustino
authors.initials: F
authors.lastname: Mollinedo
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. ismarcos@usal.es.
authors.forename: Isidro S
authors.initials: IS
authors.lastname: Marcos
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D005260:Female; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D010742:Phospholipid Ethers; D010743:Phospholipids / Q000737:chemistry*; D054830:Sesterterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D005231:Fatty Acids, Unsaturated; D010742:Phospholipid Ethers; D010743:Phospholipids; D054830:Sesterterpenes; C026659:edelfosine
keywords: PUFAs; antitumoural; bioconjugates; edelfosine; ether lipidics; sesterterpenolides