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Literature DB >> 30342865

4-N-Alkanoyl and 4-N-alkyl gemcitabine analogues with NOTA chelators for 68-gallium labelling.

Jesse Pulido¹, Maria de Cabrera¹, Adam J Sobczak¹, Alejandro Amor-Coarasa², Anthony J McGoron², Stanislaw F Wnuk³.

Abstract

The conjugation of 4-N-(3-aminopropanyl)-2'-deoxy-2',2'-difluorocytidine with 2-(p-isothiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid (SCN-Bn-NOTA) ligand in 0.1 M Na2CO3 buffer (pH 11) at ambient temperature provided 4-N-alkylgemcitabine-NOTA chelator. Incubation of latter with excess of gallium(III) chloride (GaCl3) (0.6 N AcONa/H2O, pH = 9.3) over 15 min gave gallium 4-N-alkylgemcitabine-NOTA complex which was characterized by HRMS. Analogous [68Ga]-complexation of 4-N-alkylgemcitabine-NOTA conjugate proceeded with high labeling efficiency (94%-96%) with the radioligand almost exclusively found in the aqueous layer (∼95%). The high polarity of the gallium 4-N-alkylgemctiabine-NOTA complex resulted in rapid renal clearance of the 68Ga-labelled radioligand in BALB/c mice.

Entities: CellLine Chemical Disease Gene Species

Keywords: 68-Gallium; Gemcitabine; NOTA; Nucleosides; PET imaging; Prodrugs

Mesh：

Substances：

Year: 2018 PMID： 30342865 PMCID： PMC6280190 DOI： 10.1016/j.bmc.2018.10.007

Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641

35 in total

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5. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs.

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6. Squalenoyl nanomedicines as potential therapeutics.

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4-N-Alkanoyl and 4-N-alkyl gemcitabine analogues with NOTA chelators for 68-gallium labelling.

1. Stratification of nucleoside analog chemotherapy using 1-(2'-deoxy-2'-18F-fluoro-β-D-arabinofuranosyl)cytosine and 1-(2'-deoxy-2'-18F-fluoro-β-L-arabinofuranosyl)-5-methylcytosine PET.

2. Inhibition of ribonucleotide reductase by gallium in murine leukemic L1210 cells.

3. 68Ga-complex lipophilicity and the targeting property of a urea-based PSMA inhibitor for PET imaging.

4. H-gemcitabine: a new gemcitabine prodrug for treating cancer.

5. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs.

6. Squalenoyl nanomedicines as potential therapeutics.

Review 7. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases.

8. Gemcitabine-coumarin-biotin conjugates: a target specific theranostic anticancer prodrug.

9. Noninvasive prediction of tumor responses to gemcitabine using positron emission tomography.

10. One-electron oxidation of gemcitabine and analogs: mechanism of formation of C3' and C2' sugar radicals.

1. Synthesis and ¹⁸F-radiolabeling of thymidine AMBF₃ conjugates.