Imaging Human Melanoma Using a Novel Tc-99m-labeled Lactam Bridge-cyclized Alpha-MSH Peptide

Overview

Journal Bioorg Med Chem Lett

Specialty Biochemistry

Date 2016 Aug 29

PMID 27568083

Citations 7

Authors

Liqin Liu

Jingli Xu

Jianquan Yang

Changjian Feng

Yubin Miao

Affiliations

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Abstract

In this study, the human melanoma targeting property of (99m)Tc(EDDA)-HYNIC-AocNle-CycMSHhex {hydrazinonicotinamide-8-aminooctanoic acid-Nle-c[Asp-His-DPhe-Arg-Trp-Lys]-CONH2} was determined in M21 human melanoma-xenografts to demonstrate its potential for human melanoma imaging. The IC50 value of HYNIC-AocNle-CycMSHhex was 0.48±0.01nM in M21 human melanoma cells (1281receptors/cell). The M21 human melanoma uptake of (99m)Tc(EDDA)-HYNIC-AocNle-CycMSHhex was 4.03±1.25, 3.26±1.23 and 3.36±1.48%ID/g at 0.5, 2 and 4h post-injection, respectively. Approximately 92% of injected dose cleared out the body via urinary system at 2h post-injection. (99m)Tc(EDDA)-HYNIC-AocNle-CycMSHhex showed high tumor/blood, tumor/muscle and tumor/skin uptake ratios after 2h post-injection. The M21 human melanoma-xenografted tumor lesions were clearly visualized by SPECT/CT using (99m)Tc(EDDA)-HYNIC-AocNle-CycMSHhex as an imaging probe at 2h post-injection. Overall, (99m)Tc(EDDA)-HYNIC-AocNle-CycMSHhex exhibited favorable human melanoma imaging property, highlighting its potential as an imaging probe for human metastatic melanoma detection.

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References

Siegrist W, Solca F, Stutz S, GIUFFRE L, Carrel S, Girard J . Characterization of receptors for alpha-melanocyte-stimulating hormone on human melanoma cells. Cancer Res. 1989; 49(22):6352-8. View

Raposinho P, Correia J, Alves S, Botelho M, Santos A, Santos I . A (99m)Tc(CO)(3)-labeled pyrazolyl-alpha-melanocyte-stimulating hormone analog conjugate for melanoma targeting. Nucl Med Biol. 2007; 35(1):91-9. DOI: 10.1016/j.nucmedbio.2007.08.001. View

Miao Y, Whitener D, Feng W, Owen N, Chen J, Quinn T . Evaluation of the human melanoma targeting properties of radiolabeled alpha-melanocyte stimulating hormone peptide analogues. Bioconjug Chem. 2003; 14(6):1177-84. DOI: 10.1021/bc034069i. View

Tatro J, Reichlin S . Specific receptors for alpha-melanocyte-stimulating hormone are widely distributed in tissues of rodents. Endocrinology. 1987; 121(5):1900-7. DOI: 10.1210/endo-121-5-1900. View

Chen J, Cheng Z, Hoffman T, Jurisson S, Quinn T . Melanoma-targeting properties of (99m)technetium-labeled cyclic alpha-melanocyte-stimulating hormone peptide analogues. Cancer Res. 2000; 60(20):5649-58. View

Jiang H, Kasten B, Liu H, Qi S, Liu Y, Tian M . Novel, cysteine-modified chelation strategy for the incorporation of [M(I)(CO)(3)](+) (M = Re, (99m)Tc) in an α-MSH peptide. Bioconjug Chem. 2012; 23(11):2300-12. PMC: 3525672. DOI: 10.1021/bc300509k. View

Miao Y, Owen N, Whitener D, Gallazzi F, Hoffman T, Quinn T . In vivo evaluation of 188Re-labeled alpha-melanocyte stimulating hormone peptide analogs for melanoma therapy. Int J Cancer. 2002; 101(5):480-7. DOI: 10.1002/ijc.10640. View

Raposinho P, Xavier C, Correia J, Falcao S, Gomes P, Santos I . Melanoma targeting with alpha-melanocyte stimulating hormone analogs labeled with fac-[99mTc(CO)3]+: effect of cyclization on tumor-seeking properties. J Biol Inorg Chem. 2008; 13(3):449-59. DOI: 10.1007/s00775-007-0338-3. View

Morais M, Oliveira B, Correia J, Oliveira M, Jimenez M, Santos I . Influence of the bifunctional chelator on the pharmacokinetic properties of 99mTc(CO)3-labeled cyclic α-melanocyte stimulating hormone analog. J Med Chem. 2013; 56(5):1961-73. DOI: 10.1021/jm301647t. View

10.

Kasten B, Ma X, Liu H, Hayes T, Barnes C, Qi S . Clickable, hydrophilic ligand for fac-[M(I)(CO)3](+) (M = Re/(99m)Tc) applied in an S-functionalized α-MSH peptide. Bioconjug Chem. 2014; 25(3):579-92. PMC: 3983144. DOI: 10.1021/bc5000115. View

11.

Tatro J, Wen Z, Entwistle M, Atkins M, Smith T, Reichlin S . Interaction of an alpha-melanocyte-stimulating hormone-diphtheria toxin fusion protein with melanotropin receptors in human melanoma metastases. Cancer Res. 1992; 52(9):2545-8. View

12.

Yang J, Guo H, Miao Y . Technetium-99m-labeled Arg-Gly-Asp-conjugated alpha-melanocyte stimulating hormone hybrid peptides for human melanoma imaging. Nucl Med Biol. 2010; 37(8):873-83. PMC: 2993178. DOI: 10.1016/j.nucmedbio.2010.05.006. View

13.

Miao Y, Benwell K, Quinn T . 99mTc- and 111In-labeled alpha-melanocyte-stimulating hormone peptides as imaging probes for primary and pulmonary metastatic melanoma detection. J Nucl Med. 2007; 48(1):73-80. View

14.

Siegel R, Miller K, Jemal A . Cancer statistics, 2016. CA Cancer J Clin. 2016; 66(1):7-30. DOI: 10.3322/caac.21332. View

15.

Guo H, Gallazzi F, Miao Y . Design and evaluation of new Tc-99m-labeled lactam bridge-cyclized alpha-MSH peptides for melanoma imaging. Mol Pharm. 2013; 10(4):1400-8. PMC: 3615551. DOI: 10.1021/mp3006984. View

16.

Guo H, Miao Y . Introduction of an 8-aminooctanoic acid linker enhances uptake of 99mTc-labeled lactam bridge-cyclized α-MSH peptide in melanoma. J Nucl Med. 2014; 55(12):2057-63. PMC: 4545635. DOI: 10.2967/jnumed.114.145896. View