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Literature DB >> 18359632

A novel bifunctional maleimido CHX-A'' chelator for conjugation to thiol-containing biomolecules.

Heng Xu¹, Kwamena E Baidoo, Karen J Wong, Martin W Brechbiel.

Abstract

A novel bifunctional maleimido CHX-A'' DTPA chelator 5 was developed and conjugated to the monoclonal antibody trastuzumab (Herceptin) and subsequently radiolabeled with (111)In. The resulting (111)In labeled immunoconjugate 2 was demonstrated to bind to SKOV-3 ovarian cancer cells comparably to an isothiocyanato CHX-A'' DTPA modified native trastuzumab, 1. Through efficient thiol-maleimide chemistry, antibodies, peptides or other targeting vectors can now be modified with an established radioactive metal chelating agent CHX-A'' DTPA for imaging and/or therapies of cancer.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2008 PMID： 18359632 PMCID： PMC2346453 DOI： 10.1016/j.bmcl.2008.03.022

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

19 in total

1. Spectrophotometric method for the determination of a bifunctional DTPA ligand in DTPA-monoclonal antibody conjugates.

Authors: C G Pippin; T A Parker; T J McMurry; M W Brechbiel
Journal: Bioconjug Chem Date: 1992 Jul-Aug Impact factor: 4.774

2. Maleimidocysteineamido-DOTA derivatives: new reagents for radiometal chelate conjugation to antibody sulfhydryl groups undergo pH-dependent cleavage reactions.

Authors: M R Lewis; J E Shively
Journal: Bioconjug Chem Date: 1998 Jan-Feb Impact factor: 4.774

3. Alpha-emitting bismuth cyclohexylbenzyl DTPA constructs of recombinant humanized anti-CD33 antibodies: pharmacokinetics, bioactivity, toxicity and chemistry.

Authors: T K Nikula; M R McDevitt; R D Finn; C Wu; R W Kozak; K Garmestani; M W Brechbiel; M J Curcio; C G Pippin; L Tiffany-Jones; M W Geerlings; C Apostolidis; R Molinet; M W Geerlings; O A Gansow; D A Scheinberg
Journal: J Nucl Med Date: 1999-01 Impact factor: 10.057

4. Evaluation of the in vivo biodistribution of yttrium-labeled isomers of CHX-DTPA-conjugated monoclonal antibodies.

Authors: H Kobayashi; C Wu; T M Yoo; B F Sun; D Drumm; I Pastan; C H Paik; O A Gansow; J A Carrasquillo; M W Brechbiel
Journal: J Nucl Med Date: 1998-05 Impact factor: 10.057

5. Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA.

Authors: C Wu; H Kobayashi; B Sun; T M Yoo; C H Paik; O A Gansow; J A Carrasquillo; I Pastan; M W Brechbiel
Journal: Bioorg Med Chem Date: 1997-10 Impact factor: 3.641

6. Maleimido derivatives of diethylenetriaminepentaacetic acid and triethylenetetraaminehexaacetic acid: their synthesis and potential for specific conjugation with biomolecules.

Authors: M S Ali; S M Quadri
Journal: Bioconjug Chem Date: 1996 Sep-Oct Impact factor: 4.774

7. Reassessment of diethylenetriaminepentaacetic acid (DTPA) as a chelating agent for indium-111 labeling of polypeptides using a newly synthesized monoreactive DTPA derivative.

Authors: Y Arano; T Uezono; H Akizawa; M Ono; K Wakisaka; M Nakayama; H Sakahara; J Konishi; A Yokoyama
Journal: J Med Chem Date: 1996-08-30 Impact factor: 7.446

Review 8. Targeting of radio-isotopes for cancer therapy.

Authors: Diane E Milenic; Martin W Brechbiel
Journal: Cancer Biol Ther Date: 2004-04-03 Impact factor: 4.742

Review 9. Safety and efficacy of radioimmunotherapy with yttrium 90 ibritumomab tiuxetan (Zevalin).

Authors: Hossein Borghaei; Russell J Schilder
Journal: Semin Nucl Med Date: 2004-01 Impact factor: 4.446

10. Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate).

Authors: R Jue; J M Lambert; L R Pierce; R R Traut
Journal: Biochemistry Date: 1978-12-12 Impact factor: 3.162

5 in total

A novel bifunctional maleimido CHX-A'' chelator for conjugation to thiol-containing biomolecules.

1. Spectrophotometric method for the determination of a bifunctional DTPA ligand in DTPA-monoclonal antibody conjugates.

2. Maleimidocysteineamido-DOTA derivatives: new reagents for radiometal chelate conjugation to antibody sulfhydryl groups undergo pH-dependent cleavage reactions.

3. Alpha-emitting bismuth cyclohexylbenzyl DTPA constructs of recombinant humanized anti-CD33 antibodies: pharmacokinetics, bioactivity, toxicity and chemistry.

4. Evaluation of the in vivo biodistribution of yttrium-labeled isomers of CHX-DTPA-conjugated monoclonal antibodies.

5. Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA.

6. Maleimido derivatives of diethylenetriaminepentaacetic acid and triethylenetetraaminehexaacetic acid: their synthesis and potential for specific conjugation with biomolecules.

7. Reassessment of diethylenetriaminepentaacetic acid (DTPA) as a chelating agent for indium-111 labeling of polypeptides using a newly synthesized monoreactive DTPA derivative.

Review 8. Targeting of radio-isotopes for cancer therapy.

Review 9. Safety and efficacy of radioimmunotherapy with yttrium 90 ibritumomab tiuxetan (Zevalin).

10. Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate).

1. Strategies for the preparation of bifunctional gadolinium(III) chelators.

2. Evaluation of a maleimido derivative of CHX-A'' DTPA for site-specific labeling of affibody molecules.

Review 3. Dosimetry of yttrium-labelled radiopharmaceuticals for internal therapy: 86Y or 90Y imaging?

Review 4. An Overview of Targeted Alpha Therapy with ²²⁵Actinium and ²¹³Bismuth.

5. First-in-human phase 0 study of ¹¹¹In-CHX-A"-DTPA trastuzumab for HER2 tumor imaging.

Review 8. Targeting of radio-isotopes for cancer therapy.

Review 9. Safety and efficacy of radioimmunotherapy with yttrium 90 ibritumomab tiuxetan (Zevalin).

Review 3. Dosimetry of yttrium-labelled radiopharmaceuticals for internal therapy: 86Y or 90Y imaging?

Review 4. An Overview of Targeted Alpha Therapy with 225Actinium and 213Bismuth.

Review 4. An Overview of Targeted Alpha Therapy with ²²⁵Actinium and ²¹³Bismuth.