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Chiral ligand-exchange chromatography as the screening method for proposed modifications in exametazime synthesis to enhance diastereoselectivity
dc.creator | Nikolić, N | |
dc.creator | Veselinović, D | |
dc.creator | Vladimirov, S | |
dc.creator | Karljiković-Rajić, Katarina | |
dc.creator | Lingeman, H | |
dc.date.accessioned | 2019-09-02T10:59:29Z | |
dc.date.available | 2019-09-02T10:59:29Z | |
dc.date.issued | 2004 | |
dc.identifier.issn | 0731-7085 | |
dc.identifier.uri | https://farfar.pharmacy.bg.ac.rs/handle/123456789/534 | |
dc.description.abstract | Tc-99m(V)-d,l-HM-PAO complex is well-known radiopharmaceutical for regional cerebral blood flow imaging. The proposed modifications in exametazime, hexamethylpropyleneamine oxime (HM-PAO) (4,8-diaza-3,6,6,9-tetramethylundecane-2,10-dione bisoxime) synthesis, for reduction of intermediary reactant diiminebisoxime (DI) (4,8-diaza-3,6,6,9-tetramethylundecane-3,8-diene-2,10-dione bisoxime) concerned two reductants (NaBH4 and KBH4), two solvents (ethanol and 2-propanol), and three mole ratios of reactant/reductants (1:1, 1:1.5, and 1:2). The simultaneous analysis of diastereo-enantiomeric HM-PAO content, as well as the content of starting DI, in different reduction mixtures were pet-formed using chiral ligand-exchange chromatography (CLEC). The separation of the samples of investigated reduction mixtures, obtained in the second step of HM-PAO synthesis, has been accomplished by using an achiral sorbent (RP- 18) and a chiral mobile phase (CMP) containing copper(II) complex with N,N-ditnethyl-L-phenylalanine (L-DM-PhA) as initial complex for CLEC. With 12 different reduction conditions, the obtained ratios of diastereoisomers d,l-HM-PAO: mesa-HM-PAO varied from 69.2:30.8 to 15.9:84.1, in comparison to the reduction in routine synthesis of HM-PAO which gives an equal mixture of diastereoisomers. The ternary mixed complexes formation recorded spectrophotometrically on addition of HM-PAO or DI to the mobile phase with binary complex Cu(L-DM-PhA)(2), due to the evidence of bathochromic shift of 46 nm for lambda(max) with significant difference in absorptivity contributes to separation mechanism. | en |
dc.publisher | Elsevier Science BV, Amsterdam | |
dc.rights | restrictedAccess | |
dc.source | Journal of Pharmaceutical and Biomedical Analysis | |
dc.subject | exametazime (HM-PAO) synthesis | en |
dc.subject | diastereoselective reduction | en |
dc.subject | chiral ligand-exchange chromatography (CLEC) | en |
dc.subject | diastereo-enantio separation | en |
dc.title | Chiral ligand-exchange chromatography as the screening method for proposed modifications in exametazime synthesis to enhance diastereoselectivity | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Веселиновић, Д; Карљиковић-Рајић, Катарина; Николић, Н; Владимиров, С; Лингеман, Х; | |
dc.citation.volume | 34 | |
dc.citation.issue | 2 | |
dc.citation.spage | 285 | |
dc.citation.epage | 293 | |
dc.citation.other | 34(2): 285-293 | |
dc.citation.rank | M22 | |
dc.identifier.wos | 000189331400005 | |
dc.identifier.doi | 10.1016/S0731-7085(03)00551-X | |
dc.identifier.pmid | 15013142 | |
dc.identifier.scopus | 2-s2.0-0842287434 | |
dc.type.version | publishedVersion |