Short PEG-linkers Improve the Performance of Targeted, Activatable Monoclonal Antibody-indocyanine Green Optical Imaging Probes

Overview

Journal Bioconjug Chem

Publisher American Chemical Society

Specialty Biochemistry

Date 2013 Apr 23

PMID 23600922

Citations 31

Authors

Kohei Sano

Takahito Nakajima

Kiminori Miyazaki

Yuya Ohuchi

Takashi Ikegami

Peter L Choyke

Hisataka Kobayashi

Affiliations

Soon will be listed here.

Abstract

The ability to switch optical imaging probes from the quenched (off) to the active state (on) has greatly improved target to background ratios. The optimal activation efficiency of an optical probe depends on complete quenching before activation and complete dequenching after activation. For instance, monoclonal antibody-indocyanine green (mAb-ICG) conjugates, which are promising agents for clinical translation, are normally quenched, but can be activated when bound to a cell surface receptor and internalized. However, the small fraction of commonly used ICG derivative (ICG-Sulfo-OSu) can bind noncovalently to its mAb and is, thus, gradually released from the mAb leading to relatively high background signal especially in the liver and the abdomen. In this study, we re-engineered a mAb-ICG conjugate, (Panitumumab-ICG) using bifunctional ICG derivatives (ICG-PEG4-Sulfo-OSu and ICG-PEG8-Sulfo-OSu) with short polyethylene glycol (PEG) linkers. Higher covalent binding (70-86%) was observed using the bifunctional ICG with short PEG linkers resulting in less in vivo noncovalent dissociation. Panitumumab-ICG conjugates with short PEG linkers were able to detect human epidermal growth factor receptor 1 (EGFR)-positive tumors with high tumor-to-background ratios (15.8 and 6.9 for EGFR positive tumor-to-negative tumor and tumor-to-liver ratios, respectively, at 3 d postinjection).

Citing Articles

Detection of atherosclerotic plaques with HDL-like porphyrin nanoparticles using an intravascular dual-modality optical coherence tomography and fluorescence system.

Chen R, Sandeman L, Nankivell V, Tan J, Rashidi M, Psaltis P Sci Rep. 2024; 14(1):12359.

PMID: 38811670 PMC: 11136962. DOI: 10.1038/s41598-024-63132-6.

Regulatory considerations in the design, development and quality of monoclonal antibodies and related products for the diagnosis and treatment of cancer.

Shapiro M Front Oncol. 2024; 14:1379738.

PMID: 38746685 PMC: 11091260. DOI: 10.3389/fonc.2024.1379738.

Near-infrared photoimmunotherapy targeting PD-L1: Improved efficacy by preconditioning the tumor microenvironment.

Inagaki F, Kano M, Furusawa A, Kato T, Okada R, Fukushima H Cancer Sci. 2024; 115(7):2396-2409.

PMID: 38671582 PMC: 11247602. DOI: 10.1111/cas.16195.

Advances of nanoparticle-mediated diagnostic and theranostic strategies for atherosclerosis.

Lin L, Chen L, Yan J, Chen P, Du J, Zhu J Front Bioeng Biotechnol. 2023; 11:1268428.

PMID: 38026849 PMC: 10666776. DOI: 10.3389/fbioe.2023.1268428.

Genetically Encoded 1,2-Aminothiol for Site-Specific Modification of a Cellular Membrane Protein via TAMM Condensation.

Sun H, Huang Y, Tsai Y Methods Mol Biol. 2023; 2676:191-199.

PMID: 37277634 DOI: 10.1007/978-1-0716-3251-2_14.

References

Sano K, Mitsunaga M, Nakajima T, Choyke P, Kobayashi H . In vivo breast cancer characterization imaging using two monoclonal antibodies activatably labeled with near infrared fluorophores. Breast Cancer Res. 2012; 14(2):R61. PMC: 3446396. DOI: 10.1186/bcr3167. View

Bouvet M, Hoffman R . Glowing tumors make for better detection and resection. Sci Transl Med. 2011; 3(110):110fs10. DOI: 10.1126/scitranslmed.3003375. View

Kobayashi H, Ogawa M, Alford R, Choyke P, Urano Y . New strategies for fluorescent probe design in medical diagnostic imaging. Chem Rev. 2009; 110(5):2620-40. PMC: 3241938. DOI: 10.1021/cr900263j. View

Frangioni J . New technologies for human cancer imaging. J Clin Oncol. 2008; 26(24):4012-21. PMC: 2654310. DOI: 10.1200/JCO.2007.14.3065. View

Kishimoto H, Zhao M, Hayashi K, Urata Y, Tanaka N, Fujiwara T . In vivo internal tumor illumination by telomerase-dependent adenoviral GFP for precise surgical navigation. Proc Natl Acad Sci U S A. 2009; 106(34):14514-7. PMC: 2732810. DOI: 10.1073/pnas.0906388106. View

Nakajima T, Mitsunaga M, Bander N, Heston W, Choyke P, Kobayashi H . Targeted, activatable, in vivo fluorescence imaging of prostate-specific membrane antigen (PSMA) positive tumors using the quenched humanized J591 antibody-indocyanine green (ICG) conjugate. Bioconjug Chem. 2011; 22(8):1700-5. PMC: 3157565. DOI: 10.1021/bc2002715. View

Johnson A, Karpatkin M, Newman J . [Clinical investigation of intermediate- and high-purity antihaemophilic factor (factor VIII) concentrates]. Br J Haematol. 1971; 21(1):21-41. DOI: 10.1111/j.1365-2141.1971.tb03414.x. View

Ogawa M, Kosaka N, Choyke P, Kobayashi H . In vivo molecular imaging of cancer with a quenching near-infrared fluorescent probe using conjugates of monoclonal antibodies and indocyanine green. Cancer Res. 2009; 69(4):1268-72. PMC: 2788996. DOI: 10.1158/0008-5472.CAN-08-3116. View

Harris J, Chess R . Effect of pegylation on pharmaceuticals. Nat Rev Drug Discov. 2003; 2(3):214-21. DOI: 10.1038/nrd1033. View

10.

Weissleder R, Tung C, Mahmood U, Bogdanov Jr A . In vivo imaging of tumors with protease-activated near-infrared fluorescent probes. Nat Biotechnol. 1999; 17(4):375-8. DOI: 10.1038/7933. View

11.

Sakka S . Assessing liver function. Curr Opin Crit Care. 2007; 13(2):207-14. DOI: 10.1097/MCC.0b013e328012b268. View

12.

Kobayashi H, Longmire M, Ogawa M, Choyke P . Rational chemical design of the next generation of molecular imaging probes based on physics and biology: mixing modalities, colors and signals. Chem Soc Rev. 2011; 40(9):4626-48. PMC: 3417232. DOI: 10.1039/c1cs15077d. View

13.

Zalipsky S . Functionalized poly(ethylene glycol) for preparation of biologically relevant conjugates. Bioconjug Chem. 1995; 6(2):150-65. DOI: 10.1021/bc00032a002. View

14.

Dzurinko V, Gurwood A, Price J . Intravenous and indocyanine green angiography. Optometry. 2004; 75(12):743-55. DOI: 10.1016/s1529-1839(04)70234-1. View

15.

Kishimoto H, Urata Y, Tanaka N, Fujiwara T, Hoffman R . Selective metastatic tumor labeling with green fluorescent protein and killing by systemic administration of telomerase-dependent adenoviruses. Mol Cancer Ther. 2009; 8(11):3001-8. PMC: 5529117. DOI: 10.1158/1535-7163.MCT-09-0556. View

16.

Kishimoto H, Aki R, Urata Y, Bouvet M, Momiyama M, Tanaka N . Tumor-selective, adenoviral-mediated GFP genetic labeling of human cancer in the live mouse reports future recurrence after resection. Cell Cycle. 2011; 10(16):2737-41. PMC: 3219541. DOI: 10.4161/cc.10.16.16756. View

17.

Asanuma D, Kobayashi H, Nagano T, Urano Y . Fluorescence imaging of tumors with "smart" pH-activatable targeted probes. Methods Mol Biol. 2009; 574:47-62. DOI: 10.1007/978-1-60327-321-3_5. View

18.

Roberts M, Bentley M, Harris J . Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev. 2002; 54(4):459-76. DOI: 10.1016/s0169-409x(02)00022-4. View

19.

Ono M, Watanabe R, Kawashima H, Cheng Y, Kimura H, Watanabe H . Fluoro-pegylated chalcones as positron emission tomography probes for in vivo imaging of beta-amyloid plaques in Alzheimer's disease. J Med Chem. 2009; 52(20):6394-401. DOI: 10.1021/jm901057p. View

20.

Stephenson K, Chandra R, Zhuang Z, Hou C, Oya S, Kung M . Fluoro-pegylated (FPEG) imaging agents targeting Abeta aggregates. Bioconjug Chem. 2007; 18(1):238-46. PMC: 2597429. DOI: 10.1021/bc060239q. View