Synthesis and structural characterization of complexes of a DO3A-conjugated triphenylphosphonium cation with diagnostically important metal ions.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
Read More Add to Saved list
  • Author(s): Yang CT;Yang CT; Li Y; Liu S
  • Source:
    Inorganic chemistry [Inorg Chem] 2007 Oct 15; Vol. 46 (21), pp. 8988-97. Date of Electronic Publication: 2007 Sep 05.
  • Publication Type:
    Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 0366543 Publication Model: Print-Electronic Cited Medium: Print ISSN: 0020-1669 (Print) Linking ISSN: 00201669 NLM ISO Abbreviation: Inorg Chem Subsets: MEDLINE
    • Publication Information:
      Original Publication: [Easton, Pa.] American Chemical Society.
    • Subject Terms:
      Ions*; Chemistry/*methods ; Metals/*chemistry ; Organophosphorus Compounds/*chemistry; Acetates/chemistry ; Carboxylic Acids/chemistry ; Cations ; Chromatography, High Pressure Liquid/methods ; Crystallography, X-Ray/methods ; Magnetic Resonance Spectroscopy ; Molecular Conformation ; Molecular Structure ; Salts/chemistry ; Spectrometry, Mass, Electrospray Ionization ; Spectrophotometry, Infrared/methods
    • Abstract:
      To understand the coordination chemistry of a DO3A-conjugated triphenylphosphonium (TPP) cation, triphenyl(4-((4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)methyl)benzyl)phosphonium (DO3A-xy-TPP), with diagnostically important metal ions, In(DO3A-xy-TPP)+, Ga(DO3A-xy-TPP)+, and Mn(DO3A-xy-TPP) were prepared by reacting DO3A-xy-TPP with 1 equiv of the respective metal salt. All three complexes have been characterized by elemental analysis, IR, ESI-MS, NMR methods (for In(DO3A-xy-TPP)+ and Ga(DO3A-xy-TPP)+), and X-ray crystallography. Results from HPLC concordance experiments show that (111)In(DO3A-xy-TPP)+ and In(DO3A-xy-TPP)+ have the same composition. The solid-state structures of In(DO3A-xy-TPP)+ and Mn(DO3A-xy-TPP) are very similar with DO3A being heptadentate in bonding to In(III) and Mn(II) in a monocapped octahedral coordination geometry. Because of the smaller size of Ga(III), the DO3A in Ga(DO3A-xy-TPP)+ is only hexadentate with four amine-N and two carboxylate-O atoms bonding to Ga(III). One carboxylic acid group in DO3A is deprotonated to balance the positive charge of Ga(III). The coordination geometry of Ga(DO3A-xy-TPP)+ is best described as a distorted octahedron. The NMR data shows that the coordinated DO3A in In(DO3A-xy-TPP)+ and Ga(DO3A-xy-TPP)+ is symmetrical in aqueous solution. There is no dissociation of the acetate chelating arms in In(DO3A-xy-TPP)+ and Ga(DO3A-xy-TPP)+, providing indirect evidence for the high solution stability of (111)In(DO3A-xy-TPP)+ and (68)Ga(DO3A-xy-TPP)+.
    • References:
      J Nucl Med. 1999 Jul;40(7):1180-5. (PMID: 10405140)
      Adv Drug Deliv Rev. 2001 Jul 2;49(1-2):63-70. (PMID: 11377803)
      J Nucl Med. 2002 Feb;43(2):234-8. (PMID: 11850490)
      J Biomol Screen. 2002 Aug;7(4):383-9. (PMID: 12230893)
      Methods Mol Biol. 2003;223:543-54. (PMID: 12777750)
      Inorg Chem. 2003 Dec 29;42(26):8831-7. (PMID: 14686864)
      Acta Crystallogr A. 2004 Mar;60(Pt 2):134-41. (PMID: 14966324)
      Expert Rev Mol Med. 2002 Apr 11;4(9):1-19. (PMID: 14987393)
      J Nucl Med. 2004 Apr;45(4):636-43. (PMID: 15073261)
      Mol Aspects Med. 2004 Aug;25(4):365-451. (PMID: 15302203)
      Biochemistry (Mosc). 2005 Feb;70(2):222-30. (PMID: 15807662)
      J Nucl Med. 2005 May;46(5):878-86. (PMID: 15872363)
      Biochim Biophys Acta. 2006 Feb;1762(2):140-7. (PMID: 16054341)
      Inorg Chem. 2005 Dec 26;44(26):9704-13. (PMID: 16363839)
      Biochim Biophys Acta. 2006 May-Jun;1763(5-6):561-75. (PMID: 16750866)
      Dalton Trans. 2006 Jul 21;(27):3294-9. (PMID: 16820840)
      J Nucl Med. 2006 Aug;47(8):1359-66. (PMID: 16883017)
      Breast Cancer Res Treat. 1991 Mar;18(1):57-61. (PMID: 1854980)
      J Neurosurg. 1991 Jan;74(1):116-22. (PMID: 1984490)
      Methods Enzymol. 1997;276:307-26. (PMID: 27754618)
      Proc Natl Acad Sci U S A. 1979 Feb;76(2):650-4. (PMID: 284390)
      Cancer Res. 1987 Aug 15;47(16):4361-5. (PMID: 2886218)
      J Biol Chem. 1985 Nov 5;260(25):13844-50. (PMID: 4055760)
      Proc Natl Acad Sci U S A. 1982 Sep;79(17):5292-6. (PMID: 6752944)
      Proc Natl Acad Sci U S A. 1980 Feb;77(2):990-4. (PMID: 6965798)
      J Nucl Biol Med. 1994 Sep;38(3):521-6. (PMID: 7865551)
      Biochim Biophys Acta. 1996 Jun 13;1282(1):101-6. (PMID: 8679645)
      Annu Rev Physiol. 1998;60:619-42. (PMID: 9558479)
    • Grant Information:
      R21 HL083961-01 United States HL NHLBI NIH HHS; R21 HL083961 United States HL NHLBI NIH HHS; R01 CA115883 United States CA NCI NIH HHS; R21 EB003419 United States EB NIBIB NIH HHS; 1R01CA115883-01A2 United States CA NCI NIH HHS; R21 EB003419-01A2 United States EB NIBIB NIH HHS; R21 HL083961-02 United States HL NHLBI NIH HHS; R21 EB003419-02 United States EB NIBIB NIH HHS; R01 CA115883-02 United States CA NCI NIH HHS
    • Accession Number:
      0 (Acetates)
      0 (Carboxylic Acids)
      0 (Cations)
      0 (Ions)
      0 (Metals)
      0 (Organophosphorus Compounds)
      0 (Salts)
    • Publication Date:
      Date Created: 20070906 Date Completed: 20080116 Latest Revision: 20190108
    • Publication Date:
      20231215
    • Accession Number:
      PMC2529167
    • Accession Number:
      10.1021/ic7010452
    • Accession Number:
      17784751