A convenient synthesis of bifunctional chelating agents based on diethylenetriaminepentaacetic acid and their coordination chemistry with yttrium(III)

Cummins, Clark H.; Rutter, Edward W.; Fordyce, William

doi:10.1021/bc00009a007

Cited by 43 publications

(47 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…111 In: The bifunctional chelating agent 1-(4-isothiocyanatobenzyl)diethylenetriamine penta acetic acid (SCN-Bz-DTPA) was synthesized according to the method of Cummins, et al 12) Fab-SCN-Bz-DTPA was prepared according to the procedure as reported previously, with slight modifications. 13 In, as previously reported.…”

Section: Radiolabeling Withmentioning

confidence: 99%

Noninvasive Detection of Cardiac Repair After Acute Myocardial Infarction in Rats by 111In Fab Fragment of Monoclonal Antibody Specific for Tenascin-C

et al. 2008

View full text Add to dashboard Cite

SUMMARYLeft ventricular (LV) remodeling after acute myocardial infarction (MI) causes heart failure, and thus it is important to evaluate cardiac repair as the early stage of LV remodeling. Tenascin-C (TNC), an extracellular matrix glycoprotein, is transiently and abundantly expressed in the heart during the early stage of tissue remodeling after MI. However, it is not expressed in healthy adult heart. This study was undertaken to develop a new noninvasive diagnostic technique to detect cardiac repair after acute MI using 111 In Fab fragment of a monoclonal antibody specific for TNC.111 In-anti-TNC-Fab was injected intravenously in 13 rats at 1 (D1, n = 3), 3 (D3, n = 5), and 5 (D5, n = 5) days after producing MI and in 5 sham-operated rats (S). We performed autoradiography and dual-isotope single-photon emission computed tomography imaging (SPECT) of 111 In-anti-TNC-Fab and 99mTc methoxyisobutyl isonitrile (MIBI). The radioactivity in the heart was significantly higher in D (D1, 0.45 ± 0.06% injected-dose/g; D3, 0.64 ± 0.12; D5, 0.38 ± 0.07) than S (0.27 ± 0.06, P < 0.01 versus D1 and D3, P < 0.05 versus D5). By autoradiography, higher radioactivities were observed in the infarcted area than in the noninfarcted area of MI hearts. Dual-isotope SPECT demonstrated the regional myocardial uptake of 111 In-anti-TNC-Fab, which was complementary to the perfusion image.The results of the present study indicated that we can localize the infarcted region in the heart by ex vivo and in vivo imaging methods using 111 In-anti-TNC-Fab, and suggested the potential usefulness of noninvasive detection of cardiac repair. (Int Heart J 2008; From the

show abstract

Section: Radiolabeling Withmentioning

confidence: 99%

Noninvasive Detection of Cardiac Repair After Acute Myocardial Infarction in Rats by 111In Fab Fragment of Monoclonal Antibody Specific for Tenascin-C

et al. 2008

View full text Add to dashboard Cite

show abstract

“…1,4,7,10-Tetraazacyclododecane-N,NЈ,NЉ,Nٞ -tetraacetic acid (Macrocyclics, Inc., Richardson, TX) was conjugated to cPAM4 IgG by a method described previously (62). A molar ratio of 3.3 1,4,7,10-tetraazacyclododecane-N,NЈ,NЉ,Nٞ -tetraacetic acid molecules:IgG was determined by an 111 In-binding assay (63). Radiolabeling of the cPAM4 with 111 In-chloride, performed as described previously (52), yielded a product containing 1.7% unbound radiolabel and Ͻ1% aggregated material.…”

Section: Methodsmentioning

confidence: 99%

Improved Targeting of Pancreatic Cancer

Karacay

Goldenberg

Yeldell

et al. 2004

Clinical Cancer Research

View full text Add to dashboard Cite

Purpose:The early detection and diagnosis of pancreatic cancer remains a major clinical challenge in which imaging procedures have a central role. The purpose of this study was to evaluate a pretargeting method with a bispecific PAM4 (bsPAM4; anti-MUC1) antibody for radioimmunoscintigraphy of experimental human pancreatic cancer.Experimental Design: A bispecific F(ab) 2 antibody was generated from chimeric PAM4 Fab and murine 734 (antiindium-diethylenetriaminepentaacetic acid) Fab fragments and then used in conjunction with 2 peptide haptens ( 111 In-IMP-156 and 99m Tc-IMP-192). Biodistribution studies and radioimmunoscintigraphic imaging properties of the radiolabeled bsPAM4, and pretargeted, radiolabeled peptides were examined in the CaPan1 human pancreatic tumor grown as s.c. xenografts in athymic nude mice. Tumor uptake and tumor:nontumor ratios were compared with a nontargeting irrelevant anti-CD20, bispecific rituximab, radiolabeled peptides alone, and with directly labeled PAM4.Results Conclusions: These studies demonstrate the feasibility of using the pretargeted, bispecific antibody technology for nuclear imaging of pancreatic cancer. The advantage of pretargeted bsPAM4 antibody as an imaging platform is the high specificity for pancreatic cancer as compared with the physicochemical parameters identified by current imaging technologies.

show abstract

“…Compound 4 was prepared by following a previously reported method (6). Thionyl chloride (2.0 mL, 27.41 mmol) was mixed with 40 mL of anhydrous methanol and stirred in an ice bath under nitrogen.…”

Section: Methodsmentioning

confidence: 99%

Maleimido Derivatives of Diethylenetriaminepentaacetic Acid and Triethylenetetraaminehexaacetic Acid: Their Synthesis and Potential for Specific Conjugation with Biomolecules

Ali

Quadri

1996

Bioconjugate Chem.

View full text Add to dashboard Cite

Immunoconjugates sometimes suffer changes in immunoreactivity and tumor targeting because the chelators used interfere with antigen binding. To try to circumvent such problems, two new homobifunctional chelating agents, 2,6-bis[p-[(beta-maleimidopropionyl) amino]benzyl]diethylenetriamine- N,N,N',N",N"-pentaacetic acid (MPBz-DTPA) and 2,9-bis [p-(beta-maleimidopropionyl)amino]benzyl] triethylenetetraamine-N,N,N',N',N",N"-hexaacetic acid (MPBz-TTHA), were synthesized for chelation of 111In and 90Y metal ions. Each of the new chelators contains two maleimido functional groups substituted at the carbon backbone. In this study, the overall chemical yields for MPBz-DTPA and MPBz-TTHA were approximately 5 and 4%, respectively. The intermediate and final compounds were purified by flash chromatography and fully characterized by 1H-NMR, 13C-NMR, and mass spectroscopy. Chemical modification of the maleimido group on each of these derivatives allowed specific conjugation with a sulfhydryl group at the hinge region of an antibody molecule and conjugation with other peptides. For instance, the two Fab' fragments, through their hinge-region sulfhydryl groups, could covalently attach to a homobifunctional chelator via thioether linkage to generate a Fab'-S-chelator-S-Fab' immunoconjugate. By design, immunoconjugates containing these new chelators will contain only one chelator derivative at a known region of antibody away from the antigen binding site. Consequently, these chelators may minimize changes in the immunoreactivity and improve tumor targeting of immunoconjugates that contain them.

show abstract

A convenient synthesis of bifunctional chelating agents based on diethylenetriaminepentaacetic acid and their coordination chemistry with yttrium(III)

Cited by 43 publications

References 8 publications

Noninvasive Detection of Cardiac Repair After Acute Myocardial Infarction in Rats by 111In Fab Fragment of Monoclonal Antibody Specific for Tenascin-C

Noninvasive Detection of Cardiac Repair After Acute Myocardial Infarction in Rats by 111In Fab Fragment of Monoclonal Antibody Specific for Tenascin-C

Improved Targeting of Pancreatic Cancer

Maleimido Derivatives of Diethylenetriaminepentaacetic Acid and Triethylenetetraaminehexaacetic Acid: Their Synthesis and Potential for Specific Conjugation with Biomolecules

Contact Info

Product

Resources

About