DOTA-tris(acid)-amido-dPEG®₁₂-TFP ester

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DOTA-tris(acid)-amido-dPEG®12-TFP ester, product number 11162, contains a DOTA-tris(acid) group combined with a long discrete polyethylene glycol (dPEG®) spacer and functionalized with 2,3,5,6-tetrafluorophenyl (TFP) ester. The dPEG® linker is 40 atoms (46.3 Å) long.

Polyethylene glycol (PEG) is frequently used to impart water solubility and flexibility to molecules and to reduce or eliminate immunogenicity of molecules. In vivo, PEG increases the hydrodynamic volume of molecules to which it is conjugated, because each ethylene glycol unit in a PEG chain can interact with up to three molecules of water through hydrogen bonding. Renal clearance of PEGylated conjugates is decreased or eliminated by the increased hydrodynamic volume. Reduced renal clearance means that lower doses of therapeutic agents can be administered.

Large, disperse PEG (Đ > 1) often is used to obtain the benefits of PEGylation described above. However, research over the past several years has proven that large, disperse PEG is not always needed. Moreover, in many cases, large, disperse PEG may work against the intended goals by, for example, reducing ligand affinity for a receptor or inhibiting cell internalization. By contrast, Quanta BioDesign produces only single molecular weight (that is, discrete) PEG products (that is Đ = 1). Our smaller dPEG® products avoid problems associated with large PEGs, while their discrete nature simplifies analysis of the dPEG® product and of conjugates formed with the dPEG® product. Click here and here to learn more about the advantages of dPEG® products.

The macrocycle 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) is a highly popular, effective bifunctional chelator that is used in radiopharmaceutical applications that require trivalent isotopes of yttrium or lanthanides. The four acetate groups on the macrocycle are unprotected. Therefore, this DOTA compound should be conjugated to the target molecule at the end of the synthetic process when no further reactions will be carried out. To learn more, read DOTA-tris(TBE) or DOTA-tris(acid)? Choose wisely.

The TFP ester reacts specifically and efficiently with amines. See, TFP Esters Have More Hydrolytic Stability and Greater Reactivity than NHS Esters to understand the advantages of TFP esters over N-hydroxysuccinimide (NHS) esters.

If you need bulk product in a larger package size than our standard sizes, please contact us for a quote. Our commercial capabilities permit us to manufacture this product at any scale that you need.

Application References:

  1. Hermanson, G. T. Chapter 2, Functional Targets for Bioconjugation. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, 127-228, specifically pages 191-192, discussing iodoacetates and bromoacetates reacting with thiols. Click here now for a review of Greg’s book and a link to purchase it.
  2. Hermanson, G. T. Chapter 12, Isotopic Labeling Techniques. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, 507-534, specifically pages 508-509, discussing DOTA.
  3. Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, 787-838.
  4. De León-Rodríguez, L. M.; Kovacs, Z. The Synthesis and Chelation Chemistry of DOTA−Peptide Conjugates. Bioconjugate Chem. 2008, 19(2), 391–402. https://doi.org/10.1021/bc700328s.
  5. Brechbiel, M. W. Bifunctional chelates for metal nuclides. The Quarterly Journal of Nuclear Medicine and Molecular Imaging 2008, 52(2), 166-173. https://www.minervamedica.it/en/journals/nuclear-med-molecular-imaging/article.php?cod=R39Y2008N02A0166 (accessed Feb 7, 2019).
  6. Mier, W.; Haberkorn, U.; Eisenhut, M. Synthesis and Isolation of Active Esters of DOTA. Journal of Labelled Compounds and Radiopharmaceuticals 2001, 44 (S1), S814–S816. https://doi.org/10.1002/jlcr.25804401286.

Additional information

Weight .5 oz
Dimensions .75 × .75 × 2 in

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