Radioiodination of Rhenium Cyclized α-Melanocyte-Stimulating Hormone Resulting in Enhanced Radioactivity Localization and Retention in Melanoma

Cheng, Zhen; Chen, Jianqing; Quinn, Thomas P.; Jurisson, Silvia S.

doi:10.1158/0008-5472.can-03-0193

Cited by 54 publications

(65 citation statements)

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“…The most promising melanoma-targeting peptides are linear peptide NAPamide (16) and rhenium-cyclized CCMSH peptides (9,11,15). NAPamide is a short peptide with only eight amino acid residues.…”

Section: Discussionmentioning

confidence: 99%

“…Similar to other radiometal-labeled peptides (9,11,17,21,30), high renal activity accumulation and retention of 64 Cu-DOTA-NAPamide is also observed in both tumor models ( Figure 3A and B). This could possibly be decreased by the use of L-or D-lysine without affecting tumor attention (9,15) in order to achieve a better kidney to normal tissue ratio and reduce radiation dose to the tested subject.…”

Section: Discussionmentioning

confidence: 99%

“…Briefly, cells were seeded at a density of 0.2 million/well in 24-well tissue culture plates and allowed to attach overnight. Cell uptake, internalization, and cellular retention of the 64 Cu-DOTA-NAPamide were examined in B16F10 cells using the method described previously (15). Briefly, in 24-well tissue plates prepared as described above, approximately 170 000 dpm of 64 Cu-labeled peptide (76.5 nCi, 0.283 ng, 0.38 nM) in 0.5 mL of binding media were added to each well containing cells and incubated at 37 °C for 5 min to 3 h. The nonspecific binding was determined by coincubation with nonradiolabeled NDP at a final concentration of 10 μM.…”

Section: In Vitro Cell Assaysmentioning

confidence: 99%

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⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

et al. 2007

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The alpha-melanocyte-stimulating hormone (α-MSH) receptor (melanocortin type 1 receptor, or MC1R) plays an important role in the development and growth of melanoma cells. It was found that MC1R was overexpressed on most murine and human melanoma, making it a promising molecular target for melanoma imaging and therapy. Radiolabeled α-MSH peptide and its analogs that can specifically bind with MC1R have been extensively explored for developing novel agents for melanoma detection and radionuclide therapy. The goal of this study was to evaluate a 64 Culabeled α-MSH analog, Ac-Nle-Asp-His-D-Phe-Arg-Trp-Gly-Lys(DOTA)-NH 2 (DOTANAPamide), as a potential molecular probe for microPET imaging of melanoma and MC1R expression in melanoma xenografted mouse models. 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) conjugated NAPamide was synthesized and radiolabeled with 64 Cu (t 1/2 =12 h) in NH 4 OAc (0.1 M; pH 5.5) buffered solution for 60 min at 50 °C. Cell culture studies reveal rapid and high uptake and internalization of 64 Cu-DOTA-NAPamide in B16F10 cells. Over 90% of receptor-bound tracer is internalized at 3 h incubation. A cellular retention study demonstrates that the receptor-bound 64 Cu-DOTA-NAPamide is slowly released from the B16F10 cells into the medium; 66% of the radioactivity is still associated with the cells even after 3 h incubation. The biodistribution of 64 Cu-DOTA-NAPamide was then investigated in C57BL/6 mice bearing subcutaneous murine B16F10 melanoma tumors with high capacity of MC1R and Fox Chase Scid mice bearing human A375M melanoma with a relatively low number of MC1R receptors. Tumor uptake values of 64 Cu-DOTA-NAPamide are found to be 4.63 ± 0.45% and 2.49 ± 0.31% ID/g in B16F10 and A375M xenografted melanoma at 2 h postinjection (pi), respectively. The B16F10 tumor uptake at 2 h pi is further inhibited to 2.29 ± 0.24% ID/g, while A375M tumor uptake at 2 h pi remains 2.20 ± 0.41% ID/g with a coinjection of excess α-MSH peptide. MicroPET imaging of 64 Cu-DOTA-NAPamide in B16F10 tumor mice clearly shows good tumor localization. However, low A375M tumor uptake and poor tumor to normal tissue

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: In Vitro Cell Assaysmentioning

confidence: 99%

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⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

et al. 2007

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“…There have been a number of reports on α-MSH peptide-based agents that have demonstrated the ability to image the MCR1 receptor in vivo [31][32][33][34][35][36][37][38][39]. We previously described an α-MSHtargeting peptide system, DOTA-ReCCMSH(Arg 11 ), that was labeled with β + -emitting radiometals, as potential agents for the detection of malignant melanoma via PET imaging [40].…”

Section: -[ 18 F]fluoro-2-deoxy-d-glucose ([ 18 F]fdg)mentioning

confidence: 99%

“…We previously described an α-MSHtargeting peptide system, DOTA-ReCCMSH(Arg 11 ), that was labeled with β + -emitting radiometals, as potential agents for the detection of malignant melanoma via PET imaging [40]. The rhenium cyclized peptide system was chosen for further study given its increased stability compared to its linear analog with a concomitant increase in tumor uptake and less renal retention [38,39]. We chose the divalent metal ion 64 Cu (t 1/2 = 12.7 h, 17.4% β + , 41% EC, 40% β − ) [41] and trivalent metal ion 86 Y (t 1/2 = 14.7 h, 33% β + ), both of which can be prepared on a biomedical cyclotron utilizing the 64 Ni(p,n) 64 Cu and 86 Sr(p,n) 86 Y reactions, respectively [42,43].…”

Section: -[ 18 F]fluoro-2-deoxy-d-glucose ([ 18 F]fdg)mentioning

confidence: 99%

Gallium-68-labeled DOTA-rhenium-cyclized α-melanocyte-stimulating hormone analog for imaging of malignant melanoma

Wei

Miao

Gallazzi

et al. 2007

Nuclear Medicine and Biology

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Introduction-Diagnosis of malignant melanoma is critical, since a patient's prognosis is poor. Previous studies have shown that 64 Cu-and 86 Y-DOTA-ReCCMSH(Arg 11 ) have the potential for early detection of malignant melanoma by exploiting the sensitivity and high resolution of PET. This encouraged us to investigate DOTA-ReCCMSH(Arg 11 ) labeled with another β + -emitting radionuclide, 68 Ga.Methods-DOTA-ReCCMSH(Arg 11 ) was successfully labeled with 68 Ga at pH 3.8-4 at 85 ºC. Acute biodistribution and small animal PET imaging studies were performed in B16/F1 melanoma tumor bearing mice.Results-Biodistribution studies showed moderate receptor-mediated tumor uptake, fast non-target organ clearance, and high tumor to non-target tissue ratios. Pre-administration of D-lysine significantly reduced kidney uptake without affecting the uptake of the agent in the tumor. Small animal PET images showed that the tumor could be clearly visualized at all time points examined (0.5 -2 h) with the standardized uptake value (SUV) analysis following a similar trend as the biodistribution data.Conclusions-The preliminary data obtained suggests that 68 Ga-DOTA-ReCCMSH(Arg 11 ) is a promising PET imaging agent for early detection of malignant melanoma.

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Melanocortin‐1 receptor‐targeting with radiolabeled cyclic α‐melanocyte‐stimulating hormone analogs for melanoma imaging

Raposinho¹,

Correia²,

Oliveira³

et al. 2010

Biopolymers

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Melanoma is a type of skin cancer known for its high aggressiveness, early dissemination of metastases, and poor prognosis once metastasized. Thus, early diagnosis of melanoma is a key issue for increasing patient survival. The overexpression of melanocortin-1 receptors (MC1R) in isolated melanoma cells and melanoma tissues led to the radiolabeling of several linear and cyclic MC analogs for melanoma imaging or therapy. Cyclization of α-melanocyte stimulating hormone (α-MSH) peptides has been successfully used to improve binding affinity and in vivo stability of peptides. Herein, we describe the different peptide cyclization strategies recently reported for radiolabeled α-MSH analogs and discuss how such strategies affect MC1R binding affinity, pharmacokinetic profile, and MC1R-melanoma imaging. This review also highlights how the nature of the radiometal and labeling approach influence those properties. Among the cyclized α-MSH peptides reported, (99m)Tc/(111)In-labeled metal-cyclized and lactam bridge-cyclized peptides displayed the highest melanoma and lowest renal uptake values in B16/F1 melanoma-bearing mice and became the most promising tools to be further explored as potential melanoma imaging probes.

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Radioiodination of Rhenium Cyclized α-Melanocyte-Stimulating Hormone Resulting in Enhanced Radioactivity Localization and Retention in Melanoma

Cited by 54 publications

References 20 publications

⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

Gallium-68-labeled DOTA-rhenium-cyclized α-melanocyte-stimulating hormone analog for imaging of malignant melanoma

Melanocortin‐1 receptor‐targeting with radiolabeled cyclic α‐melanocyte‐stimulating hormone analogs for melanoma imaging

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Radioiodination of Rhenium Cyclized α-Melanocyte-Stimulating Hormone Resulting in Enhanced Radioactivity Localization and Retention in Melanoma

Cited by 54 publications

References 20 publications

64Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

64Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

Gallium-68-labeled DOTA-rhenium-cyclized α-melanocyte-stimulating hormone analog for imaging of malignant melanoma

Melanocortin‐1 receptor‐targeting with radiolabeled cyclic α‐melanocyte‐stimulating hormone analogs for melanoma imaging

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⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression

⁶⁴Cu-Labeled Alpha-Melanocyte-Stimulating Hormone Analog for MicroPET Imaging of Melanocortin 1 Receptor Expression