Synthesis and evaluation of new iRGD peptide analogs for tumor optical imaging

Ye, Yunpeng; Zhu, Lei; Ma, Ying; Niu, Gang; Chen, Xiaoyuan

doi:10.1016/j.bmcl.2010.12.112

Cited by 44 publications

(39 citation statements)

References 34 publications

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“…It has high water solubility and stability, demonstrated low toxicity, high relative brightness [3], low albumin binding [5], and is available commercially [3, 4, 6]. There are several IR800 NIRF probes published for imaging targets on human tumor cells: EGFR [7, 8], EGFR-2 [9], VEGF [9, 10], GLUT [11, 12], PSMA [13, 14], CXCR4, and CXCR7 [15], and tumor vasculature, e.g., CD-105 [16], phosphatidylserine [17], phosphatidylethanolamine [18], and integrins [19]. …”

Section: Introductionmentioning

confidence: 99%

A High-Affinity Near-Infrared Fluorescent Probe to Target Bombesin Receptors

et al. 2014

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Purpose This study aimed to create new optical surgical navigation NIRF probes for prostate and breast cancers. Procedures IR800-linker-QWAVGHLM-NH2 with linker = GSG, GGG, and G-Abz4 were synthesized and characterized. IC50 for bombesin receptors (BBN-R) in PC-3 prostate and T47D breast cancer cells, fluorescence microscopy in PC-3 cells, and NIRF imaging in mice PC-3 tumor xenografts were studied. Results GGG, GSG, and G-Abz4 derivatives had IC50 (nM) for BBN-R+ PC-3 cells=187±31, 56 ±5, and 2.6±0.2 and T47D cells=383±1, 57.4±1.2, and 3.1±1.1, respectively. By microscopy the Abz4 derivative showed the highest uptake, was competed with by BBN, and had little to no binding to BBN-R− cells. In NIRF imaging the G-Abz4 probe was brighter than GGG probe in BBN-R+ tissues in vivo and tissues, tumors, and tumor slices ex vivo. Uptake could be partially blocked in BBN-R+ pancreas but not visibly in tumor. Conclusions Linker choice can dominate peptidic BBN-R binding. The G-Abz4 linker yields a higher affinity and specific BBN-R binder in this series of molecules.

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Section: Introductionmentioning

confidence: 99%

A High-Affinity Near-Infrared Fluorescent Probe to Target Bombesin Receptors

et al. 2014

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“…Conjugation to iRGD or co-administration with iRGD significantly improved the sensitivity of tumor-imaging agents and enhanced the activity of an antitumor drug (Teesalu et al, 2013). Based on the penetration function of iRGD, efforts have also been made to explore enhanced antitumor effect by linking iRGD with polymers , liposomes (Ye et al, 2011;Liu et al, 2013;Yu et al, 2013), nanoparticles (Sugahara et al, 2009). Though the improved anti-tumor effects of liposomal doxorubicin has been achieved by iRGD modification in one previous study (Yu et al, 2013), it is worth of making further research and validation.…”

Section: Introductionmentioning

confidence: 99%

A comprehensive study of iRGD-modified liposomes with improved chemotherapeutic efficacy on B16 melanoma

et al. 2014

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(2015) A comprehensive study of iRGD-modified liposomes with improved chemotherapeutic efficacy on B16 melanoma, Drug Delivery, 22:1, 10-20, DOI: 10.3109/10717544.2014 Here, iRGD-modified and doxorubicin-loaded sterically stabilized liposomes (iRGD-SSL-DOX) and passive liposomes (SSL-DOX) were prepared. A series of experiments were performed to evaluate the tissue penetration, cell penetration, tumor blood vessel damage and anti-tumor effect. The results of flow cytometry and confocal microscopy studies showed that iRGD-SSL-DOX with 5% DSPE-PEG 2000 -iRGD achieved higher cellular uptake level than that of SSL-DOX on B16 melanoma cells. iRGD-SSL-DOX also exhibited stronger cell growth inhibition in cytotoxicity experiments. The tumor penetrating effect of iRGD was further confirmed by imaging and cellular uptake studies in vivo, in which higher distribution of iRGD-modified liposomes in tumor tissue and tumor cells was observed. Moreover, iRGD-SSL-DOX displayed improved tumor growth inhibition and anti-angiogenesis with less systemic toxicity in an armpit B16 melanoma model. In conclusion, iRGD reserved its tumor-penetrating properties well when modified on the surface of liposomes at optimal density and iRGD-SSL-DOX would be a promising drug delivery system for active targeting tumor therapy.

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“…In a more recent demonstration of the utility of mixed solidand solution phase labeling using maleimide-based imaging agents, Ye et al prepared a dual-labeled interfering RGD (iRGD) analog bearing both DOTA and IRDye800 moieties [85]. In this work, the iRGD sequence (CRGDKGPDC) was prepared according to standard Fmoc/tBu protocols.…”

Section: Mixed Solid-and Solution-phase Synthesismentioning

confidence: 98%

Design of Peptide Imaging Agents for Whole-body and Intraoperative Molecular Imaging

Moss¹,

Vāvere²,

Azhdarinia³

2012

curr med chem

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Due to the growing toolkit of targeted contrast agents, molecular imaging continues to play a prominent role in the clinical care of cancer. Peptide-based imaging approaches are of particular significance due to their favorable pharmacokinetic properties, established manufacturing infrastructure, and documented clinical success in whole-body imaging. A logical extension of molecular imaging with peptides is to improve surgical outcomes in cancer through highly sensitive and specific probes which can be used intraoperatively. Advances in fluorescent imaging have resulted in various peptide labeling strategies with intraoperative indications. In this review, we focused on the evolving design of peptide imaging agents starting with the clinically used somatostatin targeting peptides. We then review the current synthetic approaches used for dual-labeled agent development and offer perspectives on optimal protection schemes that can be used for multimodal probe development.

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Synthesis and evaluation of new iRGD peptide analogs for tumor optical imaging

Cited by 44 publications

References 34 publications

A High-Affinity Near-Infrared Fluorescent Probe to Target Bombesin Receptors

A High-Affinity Near-Infrared Fluorescent Probe to Target Bombesin Receptors

A comprehensive study of iRGD-modified liposomes with improved chemotherapeutic efficacy on B16 melanoma

Design of Peptide Imaging Agents for Whole-body and Intraoperative Molecular Imaging

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