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Article: Complexation of antimony (SbV) with guanosine 5′-monophosphate and guanosine 5′-diphospho-D-mannose: Formation of both mono- and bis-adducts

TitleComplexation of antimony (SbV) with guanosine 5′-monophosphate and guanosine 5′-diphospho-D-mannose: Formation of both mono- and bis-adducts
Authors
Issue Date2005
PublisherElsevier Inc. The Journal's web site is located at http://www.elsevier.com/locate/jinorgbio
Citation
Journal Of Inorganic Biochemistry, 2005, v. 99 n. 12, p. 2257-2263 How to Cite?
AbstractIn spite of the extensive use of pentavalent antimony chemotherapy, the mechanism of its anti-leishmania action is still not clear. Here, we report the interactions of SbV, including the clinically used drug stibogluconate, with guanosine 5′-monophosphate (5′-GMP) and guanosine 5′-diphospho-d-mannose (5′-GDP-mannose) in aqueous solution. The deprotonated hydroxyl groups (-OH) of the ribose ring are shown to be the binding site for SbV, probably via chelation. Both mono- and bis-adducts were formed as determined by NMR, high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS), and both of them are stable in the pH range of 4 to around 9.5. The formation of the mono-adduct (k1 = 1.67 × 10-3 and 3.43 × 10-3 mM-1 min-1 for Sb(5′-GMP) and Sb(5′-GDP-mannose), respectively, at 298 K) was 10-fold faster than that of the bis-adduct (k2 = 0.16 × 10-3 and 0.21 × 10-3 mM-1 min-1, for Sb(5′-GMP) 2 and Sb(5′-GDP-mannose)2, respectively), and the mono-adduct was the major species in solution with the [bis-adduct]/[mono- adduct] < 0.5. The reactions of stibogluconate with 5′-GMP and 5′-GDP-mannose were slower than that of antimonate under similar conditions. © 2005 Elsevier Inc. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/167977
ISSN
2015 Impact Factor: 3.205
2015 SCImago Journal Rankings: 0.983
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChai, Yen_US
dc.contributor.authorYan, Sen_US
dc.contributor.authorWong, ILKen_US
dc.contributor.authorChow, LMCen_US
dc.contributor.authorSun, Hen_US
dc.date.accessioned2012-10-08T03:13:39Z-
dc.date.available2012-10-08T03:13:39Z-
dc.date.issued2005en_US
dc.identifier.citationJournal Of Inorganic Biochemistry, 2005, v. 99 n. 12, p. 2257-2263en_US
dc.identifier.issn0162-0134en_US
dc.identifier.urihttp://hdl.handle.net/10722/167977-
dc.description.abstractIn spite of the extensive use of pentavalent antimony chemotherapy, the mechanism of its anti-leishmania action is still not clear. Here, we report the interactions of SbV, including the clinically used drug stibogluconate, with guanosine 5′-monophosphate (5′-GMP) and guanosine 5′-diphospho-d-mannose (5′-GDP-mannose) in aqueous solution. The deprotonated hydroxyl groups (-OH) of the ribose ring are shown to be the binding site for SbV, probably via chelation. Both mono- and bis-adducts were formed as determined by NMR, high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS), and both of them are stable in the pH range of 4 to around 9.5. The formation of the mono-adduct (k1 = 1.67 × 10-3 and 3.43 × 10-3 mM-1 min-1 for Sb(5′-GMP) and Sb(5′-GDP-mannose), respectively, at 298 K) was 10-fold faster than that of the bis-adduct (k2 = 0.16 × 10-3 and 0.21 × 10-3 mM-1 min-1, for Sb(5′-GMP) 2 and Sb(5′-GDP-mannose)2, respectively), and the mono-adduct was the major species in solution with the [bis-adduct]/[mono- adduct] < 0.5. The reactions of stibogluconate with 5′-GMP and 5′-GDP-mannose were slower than that of antimonate under similar conditions. © 2005 Elsevier Inc. All rights reserved.en_US
dc.languageengen_US
dc.publisherElsevier Inc. The Journal's web site is located at http://www.elsevier.com/locate/jinorgbioen_US
dc.relation.ispartofJournal of Inorganic Biochemistryen_US
dc.subject.mesh5'-Guanylic Acid - Chemistryen_US
dc.subject.meshAnimalsen_US
dc.subject.meshAntimony - Chemistry - Pharmacologyen_US
dc.subject.meshAntimony Sodium Gluconate - Chemistry - Pharmacologyen_US
dc.subject.meshAntiprotozoal Agents - Chemistry - Pharmacologyen_US
dc.subject.meshChromatography, High Pressure Liquiden_US
dc.subject.meshGuanosine Diphosphate Mannose - Chemistryen_US
dc.subject.meshHumansen_US
dc.subject.meshKineticsen_US
dc.subject.meshLeishmania - Drug Effects - Metabolismen_US
dc.subject.meshLeishmaniasis - Drug Therapyen_US
dc.subject.meshMagnetic Resonance Spectroscopyen_US
dc.subject.meshSpectrometry, Mass, Electrospray Ionizationen_US
dc.titleComplexation of antimony (SbV) with guanosine 5′-monophosphate and guanosine 5′-diphospho-D-mannose: Formation of both mono- and bis-adductsen_US
dc.typeArticleen_US
dc.identifier.emailSun, H:hsun@hkucc.hku.hken_US
dc.identifier.authoritySun, H=rp00777en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/j.jinorgbio.2005.08.015en_US
dc.identifier.pmid16214217-
dc.identifier.scopuseid_2-s2.0-28444457462en_US
dc.identifier.hkuros121031-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-28444457462&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume99en_US
dc.identifier.issue12en_US
dc.identifier.spage2257en_US
dc.identifier.epage2263en_US
dc.identifier.isiWOS:000234100900002-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChai, Y=36785415300en_US
dc.identifier.scopusauthoridYan, S=7401744858en_US
dc.identifier.scopusauthoridWong, ILK=7102513945en_US
dc.identifier.scopusauthoridChow, LMC=7202533071en_US
dc.identifier.scopusauthoridSun, H=7404827446en_US

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