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dc.creatorNikolić, N
dc.creatorVeselinović, D
dc.creatorVladimirov, S
dc.creatorKarljiković-Rajić, Katarina
dc.creatorLingeman, H
dc.date.accessioned2019-09-02T10:59:29Z
dc.date.available2019-09-02T10:59:29Z
dc.date.issued2004
dc.identifier.issn0731-7085
dc.identifier.urihttps://farfar.pharmacy.bg.ac.rs/handle/123456789/534
dc.description.abstractTc-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.publisherElsevier Science BV, Amsterdam
dc.rightsrestrictedAccess
dc.sourceJournal of Pharmaceutical and Biomedical Analysis
dc.subjectexametazime (HM-PAO) synthesisen
dc.subjectdiastereoselective reductionen
dc.subjectchiral ligand-exchange chromatography (CLEC)en
dc.subjectdiastereo-enantio separationen
dc.titleChiral ligand-exchange chromatography as the screening method for proposed modifications in exametazime synthesis to enhance diastereoselectivityen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractВеселиновић, Д; Карљиковић-Рајић, Катарина; Николић, Н; Владимиров, С; Лингеман, Х;
dc.citation.volume34
dc.citation.issue2
dc.citation.spage285
dc.citation.epage293
dc.citation.other34(2): 285-293
dc.citation.rankM22
dc.identifier.wos000189331400005
dc.identifier.doi10.1016/S0731-7085(03)00551-X
dc.identifier.pmid15013142
dc.identifier.scopus2-s2.0-0842287434
dc.identifier.rcubconv_1472
dc.type.versionpublishedVersion


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