Towards the synthesis of new sequestring hexadentate bisphosphonic ligands for iron ion chelation

References

• Koleini, N.; Shapiro, J. S.; Geier, J.; Ardehali, H. Ironing out Mechanisms of Iron Homeostasis and Disorders of Iron Deficiency. J. Clin. Invest. 2021, 131, e148671. DOI:10.1172/JCI148671.
   PubMed Web of Science ®Google Scholar
• Liang, H.; Wu, X.; Zhao, G.; Feng, K.; Ni, K.; Sun, X. Renal Clearable Ultrasmall Single-Crystal Fe Nanoparticles for Highly Selective and Effective Ferroptosis Therapy and Immunotherapy. J. Am. Chem. Soc. 2021, 143, 15812–15823. DOI:10.1021/jacs.1c07471.
   PubMed Web of Science ®Google Scholar
• Torti, S. V.; Torti, F. M. Iron and Cancer: More Ore to be Mined. Nat. Rev. Cancer 2013, 13, 342–355. DOI:10.1038/nrc3495.
   PubMed Web of Science ®Google Scholar
• Dixon, S. J.; Stockwell, B. R. The Role of Iron and Reactive Oxygen Species in Cell Death. Nat. Chem. Biol. 2014, 10, 9–17. DOI:10.1038/nchembio.1416.
   PubMed Web of Science ®Google Scholar
• Kontoghiorghes, G. J.; Pattichi, K.; Hadjigavriel, M.; Kolnagou, A. Transfusional Iron Overload and Chelation Therapy with Deferoxamine and Deferiprone (L1). Transfus. Sci. 2000, 23, 211–223. DOI:10.1016/S0955-3886(00)00089-8.
   PubMedGoogle Scholar
• Mobarra, N.; Shanaki, M.; Ehteram, H.; Nasiri, H.; Sahmani, M.; Saeidi, M.; Goudarzi, M.; Pourkarim, H.; Azad, M. A Review on Iron Chelators in Treatment of Iron Overload Syndromes. Int. J. Hematol. Oncol. Stem Cell Res. 2016, 10, 239–247.
   PubMedGoogle Scholar
• Khan, A.; Singh, P.; Srivastava, A. Synthesis, Nature and Utility of Universal Iron Chelator – Siderophore: A Review. Microbiol. Res. 2018, 212-213, 103–111. DOI:10.1016/j.micres.2017.10.012.
   PubMed Web of Science ®Google Scholar
• Wang, Y.; Duran, E.; Nacionales, D.; Valencia, A.; Wostenberg, C.; Marinez, E. R. Carbamate Triserine Lactone Receptors for Anion Recognition. Tetrahedron Lett. 2008, 49, 6410–6412. DOI:10.1016/j.tetlet.2008.08.081.
   Web of Science ®Google Scholar
• Rastetter, W. H.; Erickson, T. J.; Venuti, M. C. Synthesis of Iron Chelators. Enterobactin, Enantioenterobactin, and a Chiral Analog. J. Org. Chem. 1981, 46, 3579–3590. DOI:https://doi.org/10.1021/jo00331a001.
   Web of Science ®Google Scholar
• Guttman, S. Synthèse De la Sér4-Ile8-Oxytocine, Une Eventuelle Hormone Hypophysaire De Certains Poissons (Isotocine). Helv. Chim. Acta 1962, 45, 2622–2627. DOI:10.1002/hlca.19620450733.
   Web of Science ®Google Scholar
• Klahn, P.; Zscherp, R.; Jimidar, C. C. Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis. Synthesis 2022, 54, 3499–3557. DOI:10.1055/a-1783-0751.
   Web of Science ®Google Scholar
• Gumienna-Kontecka, E.; Silvagni, R.; Lipinski, R.; Lecouvey, M.; Cesare Marincola, F.; Crisponi, G.; Nurchi, V. M.; Leroux, Y.; Kozlowski, H. Bisphosphonate Chelating Agents: Complexation of Fe(III) and Al(III) by 1-Phenyl-1-Hydroxymethylene Bisphosphonate and Its Analogues. Inorg. Chim. Acta 2002, 339, 111–118. DOI:10.1016/S0020-1693(02)00918-0.
   Web of Science ®Google Scholar
• Turhanen, P. A.; Vepsäläinen, J. J.; Peräniemi, S. Advanced Material and Approach for Metal Ions Removal from Aqueous Solutions. Sci. Rep. 2015, 5, 8992. DOI:10.1038/srep08992.
   PubMed Web of Science ®Google Scholar
• Abu-Shandi, K.; Winkler, H.; Janiak, C. Structure and Mössbauer Study of the First Mixed-Valence Iron Diphosphonate: 2∞[{FeII/III (H2O)2. }{FeIII/IICl}2(µ4-O3. P-C(Oh){(Ch2)4nh3}-Po3)2]·4h2o. Z. Anorg. Allg. Chem. 2006, 632, 629–633. DOI:10.1002/zaac.200500483.
   Web of Science ®Google Scholar
• Galezowska, J.; Gumienna-Kontecka, E. Phosphonates, Their Complexes and Bio-Applications: A Spectrum of Surprising Diversity. Coord. Chem. Rev. 2012, 256, 105–124. DOI:10.1016/j.ccr.2011.07.002.
   Web of Science ®Google Scholar
• Deluchat, V.; Bollinger, J.-C.; Serpaud, B.; Caullet, C. Divalent Cations Speciation with Three Phosphonate Ligands in the pH-Range of Natural Waters. Talanta 1997, 44, 897–907. DOI:10.1016/S0039-9140(96)02136-4.
   PubMed Web of Science ®Google Scholar
• Russell, R. G. G. Bisphosphonates: The First 40 Years. Bone 2011, 49, 2–19. DOI:10.1016/j.bone.2011.04.022.
   PubMed Web of Science ®Google Scholar
• Koehne, I.; Pietschnig, R. Synthesis of Geminal Bis- and Tetrakisphosphonate Ester Derivatives and Their Coordination Behavior towards Ca(II) Ions. Eur. J. Inorg. Chem. 2022, 2022, e202200194. DOI:10.1002/ejic.202200194.
   Web of Science ®Google Scholar
• Hormi, O. E. O.; Pajunen, E. O.; Avail, A.-K. C.; Pennanen, P.; Näsman, J. H.; Sundell, M. A Cheap One-Pot Approach to Tetraethyl Methylenediphosphonate. Synth. Commun. 1990, 20, 1865–1867. DOI:10.1080/00397919008053112.
   Web of Science ®Google Scholar
• Corey, E. J.; Bhattacharyya, S. Total Synthesis of Enterobactin, a Macrocyclic Iron Transporting Agent of Bacteria. Tetrahedron Lett. 1977, 18, 3919–3922. DOI:10.1016/S0040-4039(01)83390-6.
   Google Scholar
• Tor, Y.; Libman, J.; Shanzer, A.; Lifson, S. Biomimetic Ferric Ion Carriers. A Chiral Analog of Enterobactin. J. Am. Chem. Soc. 1987, 109, 6517–6518. DOI:10.1021/ja00255a050.
   Web of Science ®Google Scholar
• Winkelmann, G. CRC Handbook of Microbial Iron Chelates. 1991.
   Google Scholar
• Loomis, L. D.; Raymond, K. N. Solution Equilibria of Enterobactin and Metal-Enterobactin Complexes. Inorg. Chem. 1991, 30, 906–911. DOI:10.1021/ic00005a008.
   Web of Science ®Google Scholar
• Shanzer, A.; Libman, J.; Lifson, S.; Felder, C. E. Origin of the Iron(III) Binding and Conformational Properties of Enterobactin. J. Am. Chem. Soc. 1986, 108, 7609–7619. DOI:10.1021/ja00284a026.
   PubMed Web of Science ®Google Scholar
• Shanzer, A.; Libman, J.; Frolow, F. A Novel Series of Macrocyclic Lactones. J. Am. Chem. Soc. 1981, 103, 7339–7340. DOI:10.1021/ja00414a051.
   Web of Science ®Google Scholar
• Ramirez, R. J. A.; Karamanukyan, L.; Ortiz, S.; Gutierrez, C. G. A Much Improved Synthesis of the Siderophore Enterobactin. Tetrahedron Lett. 1997, 38, 749–752. DOI:10.1016/S0040-4039(96)02452-5.
   Web of Science ®Google Scholar
• Meyer, J. M.; Hohnadel, D.; Hallé, F. Cepabactin from Pseudomonas cepacia, a New Type of Siderophore. J. Gen. Microbiol. 1989, 135, 1479–1487. DOI:10.1099/00221287-135-6-1479.
   PubMedGoogle Scholar
• Meyer, M.; Telford, J. R.; Cohen, S. M.; White, D. J.; Xu, J.; Raymond, K. N. High-Yield Synthesis of the Enterobactin Trilactone and Evaluation of Derivative Siderophore Analogs. J. Am. Chem. Soc. 1997, 119, 10093–10103. DOI:10.1021/ja970718n.
   Web of Science ®Google Scholar
• Deleuze, H.; Maillard, B. Une Méthode Simple Et Efficace De Préparation Des Dihydrures Organotanniques. J. Organomet. Chem. 1995, 490, C14–C17. DOI:10.1016/0022-328X(94)05356-G.
   Google Scholar
• Theodorou, V.; Ragoussis, V.; Strongilos, A.; Zelepos, E.; Eleftheriou, A.; Dimitriou, M. A Convenient Method for the Preparation of Primary Amines Using Tritylamine. Tetrahedron Lett. 2005, 46, 1357–1360. DOI:10.1016/j.tetlet.2004.12.098.
   Web of Science ®Google Scholar
• Zervas, L.; Theodoropoulos, D. M. N-Tritylamino Acids and Peptides. A New Method of Peptide Synthesis. J. Am. Chem. Soc. 1956, 78, 1359–1363. DOI:10.1021/ja01588a027.
   Web of Science ®Google Scholar
• Degenhardt, C. R.; Burdsall, D. C. Synthesis of Ethenylidenebis (Phosphonic Acid) and Its Tetraalkyl Esters. J. Org. Chem. 1986, 51, 3488–3490. DOI:10.1021/jo00368a017.
   Web of Science ®Google Scholar
• Sturtz, G.; Guervenou, J. Synthesis Of Novel Functionalized gem-Bisphosphonates. Synthesis 1991, 1991, 661–662. DOI:10.1055/s-1991-26539.
   Google Scholar
• Guervenou, J.; Sturtz, G. Synthese De Conjugues Gem-Bisphosphoniques De Derives De la Cortisone. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 88, 1–13. DOI:10.1080/10426509408036901.
   Web of Science ®Google Scholar
• d‘Hardemare, A. D M.; Alnaga, N.; Serratrice, G.; Pierre, J.-L. Oxinobactin, a Siderophore Analogue to Enterobactin Involving 8-Hydroxyquinoline Subunits: Synthesis and Iron Binding Ability. Bioorg. Med. Chem. Lett. 2008, 18, 6476–6478. DOI:10.1016/j.bmcl.2008.10.060.
   PubMed Web of Science ®Google Scholar
• Coutrot, P.; Grison, C.; Charbonnier-Gérardin, C. Synthese De Peptides Modifies Incorporant Un Motif Phosphore n Ou c Terminal. Tetrahedron 1992, 48, 9841–9868. DOI:10.1016/S0040-4020(01)92278-1.
   Google Scholar
• Fabulet, O.; Sturtz, G. Synthesis of Gem-Bisphosphonic Doxorobicin Conjugates. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 101, 225–234. DOI:10.1080/10426509508042521.
   Web of Science ®Google Scholar
• Justyna, K.; Małolepsza, J.; Kusy, D.; Maniukiewicz, W.; Błażewska, K. M. The McKenna Reaction - Avoiding Side Reactions in Phosphonate Deprotection. Beilstein J. Org. Chem. 2020, 16, 1436–1446. DOI:10.3762/bjoc.16.119.
   PubMedGoogle Scholar
• Gutierrez, A. J.; Prisbe, E. J.; Rohloff, J. C. Dealkylation of Phosphonate Esters with Chlorotrimethylsilane. Nucleosides. Nucleotides Nucleic Acids. 2001, 20, 1299–1302. DOI:10.1081/NCN-100002541.
   PubMed Web of Science ®Google Scholar
• Lecouvey, M.; Leroux, Y. Synthesis of 1-Hydroxy-1,1-Bisphosphonates. Heteroatom Chem. 2000, 11, 556–561. DOI:10.1002/1098-1071(2000)11:7 < 556::AID-HC15 > 3.0.CO;2-N.
   Web of Science ®Google Scholar