2-Iodobenzoate - Explore the Science & Experts | ideXlab

Scan Science and Technology

Contact Leading Edge Experts & Companies


The Experts below are selected from a list of 327 Experts worldwide ranked by ideXlab platform

2-Iodobenzoate – Free Register to Access Experts & Abstracts

Michael R Zalutsky – One of the best experts on this subject based on the ideXlab platform.

  • observations on the effects of residualization and dehalogenation on the utility of n succinimidyl ester acylation agents for radioiodination of the internalizing antibody trastuzumab
    Molecules, 2019
    Co-Authors: Satish K Chitneni, Eftychia Koumarianou, Ganesan Vaidyanathan, Michael R Zalutsky

    Trastuzumab is an antibody used for the treatment of human epidermal growth factor receptor 2 (HER2)-overexpressing breast cancers. Since trastuzumab is an internalizing antibody, two factors could play an important role in achieving high uptake and prolonged retention of radioactivity in HER2-positive tumors after radioiodination—residualizing capacity after receptor-mediated internalization and susceptibility to dehalogenation. To evaluate the contribution of these two factors, trastuzumab was radiolabeled using the residualizing reagent N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate ([*I]SGMIB) and the nonresidualizing reagent N-succinimidyl-3-[*I]iodobenzoate ([*I]SIB), both of which are highly dehalogenation-resistant. Paired-label uptake and intracellular retention of [125I]SGMIB-trastuzumab and [131I]SIB-trastuzumab was compared on HER2-expressing BT474 human breast carcinoma cells. Tumor uptake and normal tissue distribution characteristics for the two labeled conjugates were assessed in mice bearing BT474M1 xenografts. The internalization and intracellular retention of initially-bound radioactivity in BT474 cells was similar for the two labeled conjugates up to 4 h, but were significantly higher for [125I]SGMIB-trastuzumab at 6 and 24 h. Similarly, [*I]SGMIB labeling resulted in significantly higher uptake and retention of radioactivity in BT474M1 xenografts at all studied time points. Moreover, tumor-to-tissue ratios for [125I]SGMIB-trastuzumab were consistently higher than those for [131I]SIB-trastuzumab starting at 12 h postinjection. Thus, optimal targeting of HER2-positive breast cancers with a radioiodinated trastuzumab conjugate requires an acylation agent that imparts residualizing capacity in addition to high stability towards dehalogenation in vivo.

  • Improved tumor targeting of anti-HER2 nanobody through N-succinimidyl 4guanidinomethyl-3-iodobenzoate radiolabeling. J Nucl Med 2014;55:1-7 . First paper that describes the theranostic potential of radioiodinated nanobodies
    , 2016
    Co-Authors: Marek Pruszynski, Eftychia Koumarianou, Ganesan Vaidyanathan, Kim H Lyerly, Hilde Revets, Nick Devoogdt, Tony Lahoutte, Michael R Zalutsky

    Nanobodies are approximately 15-kDa proteins based on the smallest functional fragments of naturally occurring heavy chain– only antibodies and represent an attractive platform for the devel-opment of molecularly targeted agents for cancer diagnosis and therapy. Because the human epidermal growth factor receptor type 2 (HER2) is overexpressed in breast and ovarian carcinoma, as well as in othermalignancies,HER2-specificNanobodiesmaybevaluable radiodiagnostics and therapeutics for these diseases. The aim of the present study was to evaluate the tumor-targeting potential of anti-HER2 5F7GGC Nanobody after radioiodination with the residualiz-ing agentN-succinimidyl 4-guanidinomethyl 3-125/131I-iodobenzoate (*I-SGMIB).Methods: The 5F7GGC Nanobody was radiolabeled us-ing *I-SGMIBand, for comparison,withNe-(3-*I-iodobenzoyl)-Lys5-Nα-maleimido-Gly1-GEEEK (*I-IB-Mal-D-GEEEK), another residualizing agent, andbydirect radioiodinationusing IODO-GEN (125I-Nanobody)

  • n succinimidyl guanidinomethyl iodobenzoate protein radiohalogenation agents influence of isomeric substitution on radiolabeling and target cell residualization
    Nuclear Medicine and Biology, 2014
    Co-Authors: Jaeyeon Choi, Eftychia Koumarianou, Ganesan Vaidyanathan, Darryl Mcdougald, Marek Pruszynski, Takuya Osada, T Lahoutte, Kim H Lyerly, Michael R Zalutsky

    Abstract Introduction N -succinimidyl 4-guanidinomethyl-3-[ ⁎ I]iodobenzoate ([ ⁎ I]SGMIB) has shown promise for the radioiodination of monoclonal antibodies (mAbs) and other proteins that undergo extensive internalization after receptor binding, enhancing tumor targeting compared to direct electrophilic radioiodination. However, radiochemical yields for [ 131 I]SGMIB synthesis are low, which we hypothesize is due to steric hindrance from the Boc-protected guanidinomethyl group ortho to the tin moiety. To overcome this, we developed the isomeric compound, N -succinimidyl 3-guanidinomethyl-5-[ 131 I]iodobenzoate ( iso -[ 131 I]SGMIB) wherein this bulky group was moved from ortho to meta position. Methods Boc 2 – iso -SGMIB standard and its tin precursor, N -succinimidyl 3-((1,2-bis( tert -butoxycarbonyl)guanidino)methyl)-5-(trimethylstannyl)benzoate (Boc 2 – iso -SGMTB), were synthesized using two disparate routes, and iso -[*I]SGMIB synthesized from the tin precursor. Two HER2-targeted vectors — trastuzumab (Tras) and a nanobody 5F7 (Nb) — were labeled using iso -[ ⁎ I]SGMIB and [ ⁎ I]SGMIB. Paired-label internalization assays in vitro with both proteins, and biodistribution in vivo with trastuzumab, labeled using the two isomeric prosthetic agents were performed. Results When the reactions were performed under identical conditions, radioiodination yields for the synthesis of Boc 2 – iso -[ 131 I]SGMIB were significantly higher than those for Boc 2 -[ 131 I]SGMIB (70.7±2.0% vs 56.5±5.5%). With both Nb and trastuzumab, conjugation efficiency also was higher with iso -[ 131 I]SGMIB than with [ 131 I]SGMIB (Nb, 33.1±7.1% vs 28.9±13.0%; Tras, 45.1±4.5% vs 34.8±10.3%); however, the differences were not statistically significant. Internalization assays performed on BT474 cells with 5F7 Nb indicated similar residualizing capacity over 6h; however, at 24h, radioactivity retained intracellularly for iso -[ 131 I]SGMIB-Nb was lower than for [ 125 I]SGMIB-Nb (46.4±1.3% vs 56.5±2.5%); similar results were obtained using Tras. Likewise, a paired-label biodistribution of Tras labeled using iso -[ 125 I]SGMIB and [ 131 I]SGMIB indicated an up to 22% tumor uptake advantage at later time points for [ 131 I]SGMIB-Tras. Conclusion Given the higher labeling efficiency obtained with iso -SGMIB, this residualizing agent might be of value for use with shorter half-life radiohalogens.

Michael D Threadgill – One of the best experts on this subject based on the ideXlab platform.

Chien-hong Cheng – One of the best experts on this subject based on the ideXlab platform.

Tuncer H&amp – One of the best experts on this subject based on the ideXlab platform.

  • catena-Poly[[aqua(2-iodobenzoato-κO)cobalt(II)]-μ-aqua-μ-2-iodobenzoato-κ2O:O′]
    International Union of Crystallography, 2012
    Co-Authors: Nagihan &amp, Hacali Necefo&amp, Tuncer H&amp

    The asymmetric unit of the polymeric title compound, [Co(C7H4IO2)2(H2O)2]n, contains one CoII cation, two iodobenzoate anions and two water molecules. One iodobenzoate anion and one water molecule bridge adjacent Co cations, forming a polymeric chain running along the a axis, while the other iodobenzoate anion and water molecule coordinate in a monodentate manner to the CoII cation, completing the slightly distorted octahedral geometry. In the two independent anionic ligands, the carboxylate groups are twisted away from the attached benzene rings by 51.38 (18) and 39.89 (11)°, and the two benzene rings are nearly perpendicular to each other with a dihedral angle of 86.09 (10)°. Intramolecular O—H…O hydrogen bonds between coordinating water molecules and adjacent carboxylate O atoms help to stabilize the molecular structure. In the crystal, weak C—H…O hydrogen bonds link the polymeric chains into a three-dimentional supramolecular network

  • Tetrakis(μ-2-iodobenzoato-κ2O:O′)bis[aquacopper(II)]
    International Union of Crystallography, 2012
    Co-Authors: Nagihan &amp, Hacali Necefo&amp, Tuncer H&amp

    In the centrosymmetric binuclear title complex, [Cu2(C7H4IO2)4(H2O)2], the two CuII ions [Cu…Cu = 2.6009 (5) Å] are bridged by four 2-Iodobenzoate (IB) ligands. The four nearest O atoms around each CuII ion form a distorted square-planar arrangement, the distorted square-pyramidal coordination being completed by the O atom of the water molecule at a distance of 2.1525 (16) Å. The dihedral angle between the benzene ring and the carboxylate group is 25.67 (13)° in one of the independent IB ligands and 6.44 (11)° in the other. The benzene rings of the two independent IB ligands are oriented at a dihedral angle of 86.61 (7)°. In the crystal, O—H…O interactions link the molecules into a two-dimensional network. π–π contacts between the benzene rings [centroid–centroid distances = 3.810 (2) and 3.838 (2) Å] may further stabilize the structure

  • Diaquabis(2-iodobenzoato-κO)bis(nicotinamide-κN1)copper(II)
    International Union of Crystallography, 2012
    Co-Authors: Nagihan &amp, Hacali Necefo&amp, Tuncer H&amp

    In the title complex, [Cu(C7H4IO2)2(C6H6N2O)2(H2O)2], the CuII cation is located on an inversion center and is coordinated by two monodentate 2-Iodobenzoate (IB) anions, two nicotinamide (NA) ligands and two water molecules in a distorted octahedral coordination geometry. The dihedral angle between the carboxylate group and the adjacent benzene ring is 32.12 (14)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 82.02 (5)°. The coordinating water molecule links with the carboxylate group via an intramolecular O—H…O hydrogen bond. In the crystal, N—H…O, O—H…O and weak C—H…O hydrogen bonds link the molecules into a three-dimensional supramolecular network

Jerome Waser – One of the best experts on this subject based on the ideXlab platform.

  • Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy‐Allyl Cation Synthetic Equivalents
    Angewandte Chemie (International ed. in English), 2020
    Co-Authors: Nina Declas, Jerome Waser

    We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, easily available in two steps from silyl alkynes, resulted in the stereoselective formation of substituted aryl enol ethers. The reaction was most efficient with phenols as nucleophiles, but preliminary results were also achieved for C- and N- nucleophiles. In absence of external nucleophiles, the 2-Iodobenzoate group of the reagent was transferred. The obtained aryl enol ethers could then be transformed into α-difunctionalized ketones by oxidation. The described “allyl cation“-like reactivity contrast with the well-established “vinyl-cation” behavior of alkenyl iodonium salts.