Literature DB >> 32663011

Novel [99mTc]-Tricarbonyl-NOTA-Conjugated Lactam-Cyclized Alpha-MSH Peptide with Enhanced Melanoma Uptake and Reduced Renal Uptake.

Zheng Qiao, Jingli Xu, Rene Gonzalez, Yubin Miao.   

Abstract

The purpose of this study was to examine the melanoma targeting and imaging properties of n class="Chemical">99mTc(CO)3-NOTA-GGNle-CycMSHhex {1,4,7-triazacyclononane-1,4,7-triyl-triacetic acid-GlyGlyNle-c[Asp-His-DPhe-Arg-Trp-Lys]-CONH2} and 99mTc(CO)3-NODAGA-GGNle-CycMSHhex {1,4,7-triazacyclononane,1-gluteric acid-4,7-acetic acid-GlyGlyNle-c[Asp-His-DPhe-Arg-Trp-Lys]-CONH2} on B16/F10 melanoma-bearing C57 mice to demonstrate the feasibility of NOTA/NODAGA as metal chelators for 99mTc(CO)3+ radiolabeling. NOTA/NODAGA-GGNle-CycMSHhex were synthesized using fluorenylmethoxycarbonyl (Fmoc) chemistry. The melanocortin-1 (MC1) receptor binding affinities of the peptides were determined on B16/F10 melanoma cells. The biodistribution of 99mTc(CO)3-NOTA-GGNle-CycMSHhex and 99mTc(CO)3-NODAGA-GGNle-CycMSHhex were determined on B16/F10 melanoma-bearing C57 mice at 2 h postinjection to select a lead peptide for further evaluation. The melanoma targeting and imaging properties of 99mTc(CO)3-NOTA-GGNle-CycMSHhex and 99mTc(CO)3-NODAGA-GGNle-CycMSHhex were determined on B16/F10 melanoma-bearing C57 mice. The IC50 values of NOTA/NODAGA-GGNle-CycMSHhex were 0.8 ± 0.1 and 0.9 ± 0.1 nM on B16/F10 cells. 99mTc(CO)3-NOTA-GGNle-CycMSHhex and 99mTc(CO)3-NODAGA-GGNle-CycMSHhex were readily prepared via the [99mTc(CO)3(OH2)3]+ intermediate and displayed MC1R-specific binding on B16/F10 cells. 99mTc(CO)3-NOTA-GGNle-CycMSHhex was further evaluated as a lead peptide because of its higher tumor uptake (19.76 ± 3.62% ID/g) and lower kidney uptake (1.59 ± 0.52% ID/g) at 2 h postinjection than 99mTc(CO)3-NODAGA-GGNle-CycMSHhex. The B16/F10 melanoma uptake of 99mTc(CO)3-NOTA-GGNle-CycMSHhex was 16.07 ± 4.47, 19.76 ± 3.62, 11.30 ± 2.81, and 3.16 ± 2.28% ID/g at 0.5, 2, 4, and 24 h postinjection, respectively. 99mTc(CO)3-NOTA-GGNle-CycMSHhex showed high tumor to normal organ uptake ratios after 2 h postinjection. The B16/F10 melanoma lesions were clearly visualized by SPECT/CT using 99mTc(CO)3-NOTA-GGNle-CycMSHhex as an imaging probe at 2 h postinjection. High tumor uptake, low kidney uptake, and fast urinary clearance of 99mTc(CO)3-NOTA-GGNle-CycMSHhex highlighted its potential for melanoma imaging and facilitated the evaluation of 188Re(CO)3-NOTA-GGNle-CycMSHhex for melanoma therapy.

Entities:  

Keywords:  99mTc(CO)3-NOTA-GGNle-CycMSHhex; SPECT; alpha-melanocyte-stimulating hormone; melanocortin-1 receptor; melanoma targeting

Mesh:

Substances:

Year:  2020        PMID: 32663011      PMCID: PMC7484323          DOI: 10.1021/acs.molpharmaceut.0c00606

Source DB:  PubMed          Journal:  Mol Pharm        ISSN: 1543-8384            Impact factor:   4.939


  27 in total

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3.  Cancer statistics, 2020.

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4.  Effects of the amino acid linkers on the melanoma-targeting and pharmacokinetic properties of 111In-labeled lactam bridge-cyclized alpha-MSH peptides.

Authors:  Haixun Guo; Jianquan Yang; Fabio Gallazzi; Yubin Miao
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5.  Characterization of receptors for alpha-melanocyte-stimulating hormone on human melanoma cells.

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6.  Reduction of the ring size of radiolabeled lactam bridge-cyclized alpha-MSH peptide, resulting in enhanced melanoma uptake.

Authors:  Haixun Guo; Jianquan Yang; Fabio Gallazzi; Yubin Miao
Journal:  J Nucl Med       Date:  2010-02-11       Impact factor: 10.057

7.  Survival in BRAF V600-mutant advanced melanoma treated with vemurafenib.

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8.  Survival, durable tumor remission, and long-term safety in patients with advanced melanoma receiving nivolumab.

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Journal:  J Clin Oncol       Date:  2014-03-03       Impact factor: 44.544

9.  In vivo evaluation of 188Re-labeled alpha-melanocyte stimulating hormone peptide analogs for melanoma therapy.

Authors:  Yubin Miao; Nellie K Owen; Donna Whitener; Fabio Gallazzi; Timothy J Hoffman; Thomas P Quinn
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  2 in total

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Journal:  Cancer Biother Radiopharm       Date:  2021-11-11       Impact factor: 3.099

Review 2.  MC1R and melanin-based molecular probes for theranostic of melanoma and beyond.

Authors:  Hui Shi; Zhen Cheng
Journal:  Acta Pharmacol Sin       Date:  2022-08-25       Impact factor: 7.169

  2 in total

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