Development of a peptide-based bifunctional chelator conjugated to a cytotoxic drug for the treatment of melanotic melanoma

MedChemComm
2018.0

Abstract

The cytotoxic drug gemcitabine (GEM) has been conjugated to receptor-binding peptides to target melanoma tumors. A hexapeptide having a Lys-Gly-His-Lys sequence (pep-1), an octapeptide with an Arg-Gly-Asp-Lys-Gly-His-Lys sequence (pep-2), a GEM-conjugated Lys-Gly-His-Lys peptide (GEM-pep-3) and a GEM-conjugated Asp-Gly-Arg peptide (GEM-pep-4) were synthesized and characterized. <i>In vitro</i> uptake of fluorescently labeled GEM-pep-3 and GEM-pep-4 on B16F10 cells was investigated. Fluorescence microscopy studies demonstrated significant uptake of GEM-pep-3 in the B16F10 mouse melanoma cell line. The peptides and GEM-coupled peptides were radiolabeled with [<sup>99m</sup>Tc(CO)<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub>]<sup>+</sup> and examined for <i>in vitro</i> cell binding in the B16F10 melanoma cell line and <i>in vivo</i> biodistribution and scintigraphic studies in a B16F10 melanoma tumor-bearing mice model. <i>In vitro</i> cellular uptake studies and biological evaluation confirmed significant deposition of GEM-pep-3 at the melanoma tumor site. The MTT assay depicted higher cytotoxic behaviour of GEM-pep-3 than free GEM. A considerable amount of cell apoptosis was also observed in B16F10 cells. Finally, the <i>in vivo</i> therapeutic efficacy study revealed a significant decrease in tumor growth in the GEM-pep-3-treated animal model. These studies reveal enough potentiality of GEM-pep-3 to treat melanoma and underline the need for further evaluation.

Knowledge Graph

Similar Paper

Development of a peptide-based bifunctional chelator conjugated to a cytotoxic drug for the treatment of melanotic melanoma
MedChemComm 2018.0
Gemcitabine anti-proliferative activity significantly enhanced upon conjugation with cell-penetrating peptides
Bioorganic &amp; Medicinal Chemistry Letters 2017.0
Development of potent CPP6–gemcitabine conjugates against human prostate cancer cell line (PC-3)
RSC Medicinal Chemistry 2020.0
Integrin-Mediated Targeted Cancer Therapy Using c(RGDyK)-Based Conjugates of Gemcitabine
Journal of Medicinal Chemistry 2022.0
Development of bioactive gemcitabine-D-Lys6-GnRH prodrugs with linker-controllable drug release rate and enhanced biopharmaceutical profile
European Journal of Medicinal Chemistry 2019.0
Overcoming drug resistance by cell-penetrating peptide-mediated delivery of a doxorubicin dimer with high DNA-binding affinity
European Journal of Medicinal Chemistry 2017.0
Identification of Novel Medulloblastoma Cell-Targeting Peptides for Use in Selective Chemotherapy Drug Delivery
Journal of Medicinal Chemistry 2020.0
Synthesis and Biological Evaluation of Dimeric RGD Peptide−Paclitaxel Conjugate as a Model for Integrin-Targeted Drug Delivery
Journal of Medicinal Chemistry 2005.0
In Silico Exploration and Biological Evaluation of Bispecific Peptides Derived from Anti-HER2 Antibodies and Peptide–Camptothecin Conjugates for HER2-Positive Breast Cancer
Journal of Medicinal Chemistry 2022.0
Synthesis, biological studies and molecular dynamics of new anticancer RGD-based peptide conjugates for targeted drug delivery
Bioorganic &amp; Medicinal Chemistry 2016.0