Highly Stable and Inert Complexation of Indium(III) by Reinforced Cyclam Dipicolinate and a Bifunctional Derivative for Bead Encoding in Mass Cytometry

Grenier, Laura; Beyler, Maryline; Platas‐Iglesias, Carlos; Closson, Taunia L. L.; Esteban‐Gómez, David; Seferos, Dwight S.; Liu, Peng; Ornatsky, Olga; Baranov, Vladimir; Tripier, Raphaël

doi:10.1002/chem.201903969

Cited by 9 publications

(15 citation statements)

References 59 publications

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“…These calculations showed that on average only 17 amine groups per chain were + was directly grafted onto polyamino beads. 19 In this + strongly suggests that the coupling of the complex on the polymer occurred. However, the signals of the biotin end-group cannot be clearly identified, which makes it difficult to calculate the number of grafted indium complexes by NMR.…”

Section: Preparation Of the Indium Polymermentioning

confidence: 85%

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclam-Based Chelating Polylysine

et al. 2020

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The synthesis of a polylysine polymer functionalized with the previously reported astonishingly inert [In(cb-te2pa)] + chelate was performed. A biotin end group allowed the conjugation to biotinylated beads by the intermediary of a Fluorescein isothiocyanate / neutravidin receptor. High quality Imaging Mass Cytometry TM trials, based on 115 In detection were performed to highlight the behavior of the material. Anti-CD20 antibody was labeled by the so obtained In(III) modified polylysine using the biotin/neutravidin interaction. Ramos (CD20[+]) and HL-60 (CD20[-]) cell lines were co-stained with the In(III) modified bioconjugate by finding the best staining conditions. Both immunofluorescence IF-M and Mass Cytometry analyses confirmed the specific binding of anti-CD20 onto Ramos cells. CyTOF R histograms constructed on the 115 In detection allowed to define and to separate, with a good signal-to-noise ratio, two populations (Ramos and HL-60). The inertness of In(III)-MCP-Nav over a three-month storage period was proved by performing new functionality tests involving Jurkat cells (CD20[-]) as well as the possibility of multiplexing trials involving the 115 In channel. The results assure a promising future use of the previously announced [In(cb-te2pa)] + complex based polymers for mass cytometry. Electronic Supplementary Information (ESI) available: [1H NMR of TFA-Lys-NCA, Poly(TFA-L-Lys)-Btn, Poly(L-Lys)-Btn and (PEGpoly(L-Lys)-Btn); GPC chromatogram of Poly(L-Lys)-Btn; NMR integration for PEG number evaluation;. Selected areas of blanks' and beads' 115 In integral intensities on IMC images of indium beads; Average 154 Sm counts per cell for Jurkat (CD45[+]) and Ramos (CD45[+]) cells; Overlayed histograms of Jurkat and Ramos cells].

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Section: Preparation Of the Indium Polymermentioning

confidence: 85%

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclam-Based Chelating Polylysine

et al. 2020

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“…+ was directly grafted onto polyamino beads. 19 In this work, the covalent attachment of the indium complex [In(p-NCS-CH 2 Ph-cb-te2pa)] + on the polylysine polymer PEG-poly(L-Lys)-Btn was also assured through the formation of very strong thiourea bonds (Figure 3). + strongly suggests that the coupling of the complex on the polymer occurred.…”

Section: Preparation Of the Indium Polymermentioning

confidence: 79%

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclambased Chelating Polylysine

Grenier¹,

Beyler²,

Closson³

et al. 2020

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A metal containing polymer (MCP) based on a polylysine functionalized by In(III) chelates was synthesized. The chelator is based on a constrained dipicolinate cyclam that forms a highly inert In(III) complex. The MCP was conjugated to anti CD20 antibody using the very strong neutravidin/biotin interaction. Two cell lines, one expressing CD20 the other not, were stained with the modified antibody and analysed by mass cytometry using the In-115 channel. The results showed a specific antigen-antibody recognition and images by mass cytometry imaging could be obtained thanks to In-115 detection. Finally, overtime stability tests of the bioconjugate as well as multiplex experiments using the In-115 channel underline the high potentiel of this new In based MCP. <br><p></p>

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“…All the ligands presented in this paper were synthesized as previously described in the literature. − , Among them, the C- functionalized constrained cyclam derivatives have a structural interest because of the two potentially different relative positions of the ethylene cross-bridge and the C -appended hydroxyethyl pendant. During the synthesis, CB-cyclam-E and CB-DMC-E provided a mixture of syn and anti diastereoisomers as previously observed in our previous investigations . Crystals suitable for X-ray diffraction experiments, obtained from a solution containing a mixture of the two isomers, show evidence of the presence of both isomers (see Figure S3 and Table S1) in the crystal lattice.…”

Section: Results and Discussionmentioning

confidence: 95%

Complexation of C-Functionalized Cyclams with Copper(II) and Zinc(II): Similarities and Changes When Compared to Parent Cyclam Analogues

et al. 2021

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Herein, we report a comprehensive coordination study of the previously reported ligands cyclam, CB-cyclam TMC, DMC, CB-DMC, and of their C-functional analogues, cyclam-E, CB-cyclam-E, TMC-E, DMC-E and CB-DMC-E. This group of ligands includes cyclam, cross-bridged cyclams, their di-or tetramethylated derivatives and the analogues bearing an additional hydroxyethyl group on one β-N position of the ring. These Cu(II) and Zn(II) complexes of these macrocycles have been highlighted previously for the biological interest, but the details of their structures in the solid state and in solution remained largely unexplored. In particular, we analyzed the impact that adding non-coordinating Nmethyl and C-hydroxyethyl functionalities has in the structures of the complexes. All the Cu(II) and Zn(II) complexes were synthetized and investigated using single crystal X-ray diffraction and NMR, electronic absorption and EPR spectroscopies, along with DFT studies. Dissociation kinetics experiments in acidic conditions and an electrochemical study were also performed. A special attention was paid to analyze the different configurations present in solution and in the solid state, as well as the impact of the Cappended hydroxyethyl group on the coordination behavior. Various ratios of the trans-I, trans-III, and cis-V configurations have been observed depending on the degree of N-methylation and the presence of the ethylene cross-bridge.

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Highly Stable and Inert Complexation of Indium(III) by Reinforced Cyclam Dipicolinate and a Bifunctional Derivative for Bead Encoding in Mass Cytometry

Cited by 9 publications

References 59 publications

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclam-Based Chelating Polylysine

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclam-Based Chelating Polylysine

Enabling Indium Channels for Mass Cytometry by Using Reinforced Cyclambased Chelating Polylysine

Complexation of C-Functionalized Cyclams with Copper(II) and Zinc(II): Similarities and Changes When Compared to Parent Cyclam Analogues

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