Ultrasensitive detection of malignant melanoma using PET molecular imaging probes

Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synth...

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Published inProceedings of the National Academy of Sciences - PNAS Vol. 117; no. 23; pp. 12991 - 12999
Main Authors Pyo, Ayoung, Kim, Dong-Yeon, Kim, Heejung, Lim, Daejin, Kwon, Seong Young, Kang, Sae-Ryung, Kim, Hyung-Seok, Bom, Hee-Seung, Min, Jung-Joon
Format Journal Article
LanguageEnglish
Published United States National Academy of Sciences 09.06.2020
Subjects
Benzamide
Biological Sciences
Diagnosis
Dosage
Fluorine isotopes
Image quality
Lymph nodes
Medical imaging
Melanoma
Metastases
Metastasis
Physical Sciences
Positron emission
Positron emission tomography
Pyridines
Radiochemistry
Retention
Skin cancer
Synthesis
Tomography
Tracers
Tumors
Xenografts
Xenotransplantation
malignant melanoma
molecular imaging
metastasis
18F-labeled pyridine-based benzamide derivative
PET
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Abstract Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18F-labeled pyridine-based benzamide derivatives N-(2-(dimethylamino)ethyl)-5-[18F]fluoropicolinamide ([18F]DMPY2) and N-(2-(dimethylamino)ethyl)-6-[18F]fluoronicotinamide ([18F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [18F]DMPY2 and [18F]DMPY3 were synthesized by direct radio-fluorination of the bromo precursor, and radiochemical yields were ∼15–20%. Cell uptakes of [18F]DMPY2 and [18F]DMPY3 were >103- fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [18F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [18F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [18F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [18F] DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [18F]fluorodeoxyglucose ([18F]FDG) and the previously reported benzamide tracers N-[2-(diethylamino)-ethyl]-5-[18F]fluoropicolinamide ([18F]P3BZA) and N-[2-(diethylamino)-ethyl]-4-[18F]fluorobenzamide ([18F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [18F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
AbstractList Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the F-labeled pyridine-based benzamide derivatives -(2-(dimethylamino)ethyl)-5-[ F]fluoropicolinamide ([ F]DMPY2) and -(2-(dimethylamino)ethyl)-6-[ F]fluoronicotinamide ([ F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [ F]DMPY2 and [ F]DMPY3 were synthesized by direct radiofluorination of the bromo precursor, and radiochemical yields were ∼15-20%. Cell uptakes of [ F]DMPY2 and [ F]DMPY3 were >103-fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [ F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [ F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [ F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [ F]DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [ F]fluorodeoxyglucose ([ F]FDG) and the previously reported benzamide tracers -[2-(diethylamino)-ethyl]-5-[ F]fluoropicolinamide ([ F]P3BZA) and -[2-(diethylamino)-ethyl]-4-[ F]fluorobenzamide ([ F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [ F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
With the emergence of new therapeutic modalities, the diagnosis of melanoma at the earliest practicable stage has become more important for improving the survival of patients. We developed a positron emission tomography (PET) imaging probe, N -(2-(dimethylamino)ethyl)-5-[ 18 F]fluoropicolinamide ([ 18 F]DMPY2) and evaluated diagnostic performance in animal models. [ 18 F]DMPY2 PET exhibited excellent performance in detecting primary and metastatic melanomas, demonstrating strong/prolonged tumoral uptake and rapid background clearance. This suggests that this radiotracer could be used as a novel PET imaging agent to obtain outstanding image quality in the diagnosis of melanoma. This is the pioneering report of pyridine-based benzamide derivative with reduced alkyl chains in the amine residue and ultrasensitive detection of melanoma lesions in living subjects compared to conventional PET imaging agents. Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18 F-labeled pyridine-based benzamide derivatives N -(2-(dimethylamino)ethyl)-5-[ 18 F]fluoropicolinamide ([ 18 F]DMPY2) and N -(2-(dimethylamino)ethyl)-6-[ 18 F]fluoronicotinamide ([ 18 F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [ 18 F]DMPY2 and [ 18 F]DMPY3 were synthesized by direct radiofluorination of the bromo precursor, and radiochemical yields were ∼15–20%. Cell uptakes of [ 18 F]DMPY2 and [ 18 F]DMPY3 were >103-fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [ 18 F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [ 18 F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [ 18 F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [ 18 F]DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [ 18 F]fluorodeoxyglucose ([ 18 F]FDG) and the previously reported benzamide tracers N -[2-(diethylamino)-ethyl]-5-[ 18 F]fluoropicolinamide ([ 18 F]P3BZA) and N -[2-(diethylamino)-ethyl]-4-[ 18 F]fluorobenzamide ([ 18 F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [ 18 F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18F-labeled pyridine-based benzamide derivatives N-(2-(dimethylamino)ethyl)-5-[18F]fluoropicolinamide ([18F]DMPY2) and N-(2-(dimethylamino)ethyl)-6-[18F]fluoronicotinamide ([18F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [18F]DMPY2 and [18F]DMPY3 were synthesized by direct radio-fluorination of the bromo precursor, and radiochemical yields were ∼15–20%. Cell uptakes of [18F]DMPY2 and [18F]DMPY3 were >103- fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [18F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [18F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [18F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [18F] DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [18F]fluorodeoxyglucose ([18F]FDG) and the previously reported benzamide tracers N-[2-(diethylamino)-ethyl]-5-[18F]fluoropicolinamide ([18F]P3BZA) and N-[2-(diethylamino)-ethyl]-4-[18F]fluorobenzamide ([18F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [18F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18F-labeled pyridine-based benzamide derivatives N-(2-(dimethylamino)ethyl)-5-[18F]fluoropicolinamide ([18F]DMPY2) and N-(2-(dimethylamino)ethyl)-6-[18F]fluoronicotinamide ([18F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [18F]DMPY2 and [18F]DMPY3 were synthesized by direct radiofluorination of the bromo precursor, and radiochemical yields were ∼15-20%. Cell uptakes of [18F]DMPY2 and [18F]DMPY3 were >103-fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [18F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [18F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [18F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [18F]DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [18F]fluorodeoxyglucose ([18F]FDG) and the previously reported benzamide tracers N-[2-(diethylamino)-ethyl]-5-[18F]fluoropicolinamide ([18F]P3BZA) and N-[2-(diethylamino)-ethyl]-4-[18F]fluorobenzamide ([18F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [18F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18F-labeled pyridine-based benzamide derivatives N-(2-(dimethylamino)ethyl)-5-[18F]fluoropicolinamide ([18F]DMPY2) and N-(2-(dimethylamino)ethyl)-6-[18F]fluoronicotinamide ([18F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [18F]DMPY2 and [18F]DMPY3 were synthesized by direct radiofluorination of the bromo precursor, and radiochemical yields were ∼15-20%. Cell uptakes of [18F]DMPY2 and [18F]DMPY3 were >103-fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [18F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [18F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [18F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [18F]DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [18F]fluorodeoxyglucose ([18F]FDG) and the previously reported benzamide tracers N-[2-(diethylamino)-ethyl]-5-[18F]fluoropicolinamide ([18F]P3BZA) and N-[2-(diethylamino)-ethyl]-4-[18F]fluorobenzamide ([18F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [18F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the disease at the time of diagnosis is very important for the prognosis and outcome of melanoma treatment. In this study, we designed and synthesized the 18F-labeled pyridine-based benzamide derivatives N-(2-(dimethylamino)ethyl)-5-[18F]fluoropicolinamide ([18F]DMPY2) and N-(2-(dimethylamino)ethyl)-6-[18F]fluoronicotinamide ([18F]DMPY3) to detect primary and metastatic melanoma at an early stage and evaluated their performance in this task. [18F]DMPY2 and [18F]DMPY3 were synthesized by direct radiofluorination of the bromo precursor, and radiochemical yields were ∼15–20%. Cell uptakes of [18F]DMPY2 and [18F]DMPY3 were >103-fold and 18-fold higher, respectively, in B16F10 (mouse melanoma) cells than in negative control cells. Biodistribution studies revealed strong tumor uptake and retention of [18F]DMPY2 (24.8% injected dose per gram of tissue [ID/g] at 60 min) and [18F]DMPY3 (11.7%ID/g at 60 min) in B16F10 xenografts. MicroPET imaging of both agents demonstrated strong tumoral uptake/retention and rapid washout, resulting in excellent tumor-to-background contrast in B16F10 xenografts. In particular, [18F]DMPY2 clearly visualized almost all metastatic lesions in lung and lymph nodes, with excellent image quality. [18F]DMPY2 demonstrated a significantly higher tumor-to-liver ratio than [18F]fluorodeoxyglucose ([18F]FDG) and the previously reported benzamide tracers N-[2-(diethylamino)-ethyl]-5-[18F]fluoropicolinamide ([18F]P3BZA) and N-[2-(diethylamino)-ethyl]-4-[18F]fluorobenzamide ([18F]FBZA) in B16F10-bearing or SK-MEL-3 (human melanoma)-bearing mice. In conclusion, [18F]DMPY2 might have strong potential for the diagnosis of early stage primary and metastatic melanoma using positron emission tomography (PET).
Author Kwon, Seong Young
Min, Jung-Joon
Kim, Hyung-Seok
Bom, Hee-Seung
Kim, Heejung
Lim, Daejin
Pyo, Ayoung
Kang, Sae-Ryung
Kim, Dong-Yeon
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Copyright Copyright © 2020 the Author(s). Published by PNAS.
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Issue 23
Keywords malignant melanoma
molecular imaging
metastasis
18F-labeled pyridine-based benzamide derivative
PET
Language English
License Copyright © 2020 the Author(s). Published by PNAS.
This open access article is distributed under Creative Commons Attribution-NonCommercial-NoDerivatives License 4.0 (CC BY-NC-ND).
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Author contributions: D.-Y.K. and J.-J.M. designed research; A.P., D.-Y.K., H.K., and D.L. performed research; A.P., D.-Y.K., S.Y.K., S.-R.K., H.-S.K., and H.-S.B. analyzed data; and A.P., D.-Y.K., and J.-J.M. wrote the paper.
Edited by Michael E. Phelps, David Geffen School of Medicine at University of California, Los Angeles, CA, and approved April 21, 2020 (received for review December 18, 2019)
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Snippet Malignant melanoma has one of the highest mortality rates of any cancer because of its aggressive nature and high metastatic potential. Clinical staging of the...
With the emergence of new therapeutic modalities, the diagnosis of melanoma at the earliest practicable stage has become more important for improving the...
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SubjectTerms Benzamide
Biological Sciences
Diagnosis
Dosage
Fluorine isotopes
Image quality
Lymph nodes
Medical imaging
Melanoma
Metastases
Metastasis
Physical Sciences
Positron emission
Positron emission tomography
Pyridines
Radiochemistry
Retention
Skin cancer
Synthesis
Tomography
Tracers
Tumors
Xenografts
Xenotransplantation
Title Ultrasensitive detection of malignant melanoma using PET molecular imaging probes
URI https://www.jstor.org/stable/26968345
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