Chemical Name: Trisodium hydrogen [cyclo[L-arginylglycyl-L-aspartyl-3-(aminomethyl)-5-[6-[6-(diazenyl-kappaN2)-3-pyridylcarboxamido]hexanamido]benzoyl-D-valylato(2-)]][N-[2-hydroxy-1,1-bis[(hydroxy-kappaO)methyl]ethyl]glycinato(2-)-kappaN,kappaO][3,3',3''-(phosphinidyne-kappaP)tris(benzenesulfonato)(3-)]technetate(4-)-99Tc
CAS No. 206763-88-4
项目整合开发状态: Phase III
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The title ternary ligand technetium-99m complex was formed as a mixture of two isomeric forms by reaction of the hydrazinonicotinamide-derivatized cyclic peptide (I) with trisodium triphenylphosphine-3,3',3''-trisulfonate (II) and tricine (III) in the presence of 99mTc pertechnetate and SnCl2.The 99Tc analogue was similarly prepared for spectroscopic characterization by using (n-Bu4N)(99TcOCl4) or (NH4)(99TcO4).
📄 详细内容
合成路线:The title compound was then obtained by complexation of hydrazone (IX) with phosphine (II) and tricine (III) in the presence of Na99mTcO4 and SnCl2.Under these conditions,the hydrazone protecting group hydrolyzed to the required hydrazine.Some shortcomings caused by SnCl2 could be omitted using a non-SnCl2-containing formulation in the presence of mannitol and pluronic acid as surfactant agents.
参考文献标题:Towards developing A non-SnCl2 formulation for RP444,a new radiopharmaceutical for thrombus imaging
文献作者:Liu,S.; Edwards,D.S.; Harris,A.R.; Ziegler,M.C.; Poirier,M.J.; Ewels,B.A.; Diluzio,W.R.; Hui,P.
参考来源:J Pharm Sci 2001,90(2),114
合成路线:In order to stabilize the hydrazino compound (I),a stable hydrazone derivative was prepared by two alternative procedures.Condensation of 6-hydrazinonicotinic acid (IV) with sodium 2-formylbenzenesulfonate (V) gave the hydrazone acid (VI),which was further converted to the succinimidyl active ester (VII) by treatment with N-hydroxysuccinimide and DCC.Coupling of succinimidyl ester (VII) with the aminocaproyl cyclic peptide (VIII) then gave the target hydrazone derivative (IX).Alternatively,(IX) was also prepared by condensation of the hydrazino peptide (I) with sodium 2-formylbenzenesulfonate (V).
参考文献标题:Synthesis of stable hydrazones of a hydrazinonicotinyl-modified peptide for the preparation of 99mTc-labeled radiopharmaceuticals
文献作者:Harris,T.D.; et al.
参考来源:Bioconjugate Chem 1999,10(5),808
合成路线:The title compound was then obtained by complexation of hydrazone (IX) with phosphine (II) and tricine (III) in the presence of Na99mTcO4 and SnCl2.Under these conditions,the hydrazone protecting group hydrolyzed to the required hydrazine.Some shortcomings caused by SnCl2 could be omitted using a non-SnCl2-containing formulation in the presence of mannitol and pluronic acid as surfactant agents.
参考文献标题:99mTc-Labeling of hydrazones of a hydrazinonicotinamide conjugated cyclic peptide
文献作者:Edwards,D.S.; et al.
参考来源:Bioconjugate Chem 1999,10(5),803
合成路线:The title ternary ligand technetium-99m complex was formed as a mixture of two isomeric forms by reaction of the hydrazinonicotinamide-derivatized cyclic peptide (I) with trisodium triphenylphosphine-3,3',3''-trisulfonate (II) and tricine (III) in the presence of 99mTc pertechnetate and SnCl2.The 99Tc analogue was similarly prepared for spectroscopic characterization by using (n-Bu4N)(99TcOCl4) or (NH4)(99TcO4).
参考文献标题:Technetium complexes of a hydrazinonicotinamide-conjugated cyclic peptide and 2-hydrazinopyridine: synthesis and characterization
文献作者:Liu,S.; Edwards,D.S.; Harris,A.R.; Heminway,S.J.; Barrett,J.A.
参考来源:Inorg Chem 1999,38(6),1326