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Initial Evaluation of Antibody-conjugates Modified with Viral-derived Peptides for Increasing Cellular Accumulation and Improving Tumor Targeting

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Published on: March 8, 2018

PESIN Conjugates for Multimodal Imaging: Can Multimerization Compensate Charge Influences on Cell Binding Properties?

Ralph Hübner^1,2, Alexa Paretzki², Valeska von Kiedrowski³

¹Biomedical Chemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, Theodor-Kutzer-Ufer 1-3, 68167 Mannheim, Germany.

Pharmaceuticals (Basel, Switzerland)

|July 2, 2021

Summary

This summary is machine-generated.

Increasing peptide valency in multimodal imaging units (MIUs) can mitigate negative charge effects on gastrin-releasing peptide receptor (GRPR) binding. Higher valency MIUs show improved GRPR affinities, aiding in targeted imaging applications.

Keywords:

GRPR affinity NIR fluorescent dyes PESIN multimers cell binding copper-64 gallium-68 indocyanine dyes multimodal imaging

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Area of Science:

Radiochemistry
Molecular Imaging
Medicinal Chemistry

Background:

Anionic charges negatively impact in vitro gastrin-releasing peptide receptor (GRPR) binding of labeled peptide dimers.
The effect of peptide multimerization valency on GRPR binding affinities remains underexplored.

Purpose of the Study:

To investigate if increased peptide valency can mitigate the adverse effects of negative charges on GRPR binding.
To design and synthesize novel multimodal imaging units (MIUs) with varying peptide valencies.

Main Methods:

Designed hybrid MIUs with one or two click chemistry functional groups.
Synthesized peptide homodimers and homotetramers using PESIN (PEG3-BBN7-14) and MIUs.
Evaluated photophysical properties, radiolabeling efficiency (68Ga, 64Cu), hydrophilicity, and GRPR binding affinities (IC50).

Main Results:

Hydrophilicity and GRPR binding affinities were influenced by negative charges and peptide copy number.
Homodimers showed logP = -2.2 ± 0.1 and IC50 = 59.1 ± 1.5 nM.
Homotetramers showed logP = -1.9 ± 0.1 and IC50 = 99.8 ± 3.2 nM.

Conclusions:

Increased peptide valency in dually labeled PESIN multimers can partially compensate for the negative influence of charged building blocks on GRPR binding.
Molecular design and the number of peptide binding motives are crucial for optimizing GRPR affinities in multimodal imaging agents.