Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[18F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET

Yunming Ying; Pradip Ghosh; Liwei Guo; Ashutosh Pal; Uday Mukhapadhyay; Zhenghong Peng; Hsin Hsien Yeh; Susanna Bertolini; Leo Garcia Flores; Daniel Young; Andrei Volgin; Suren Soghomonyan; William Bornmann; Craig Logsdon; Mian M. Alauddin; Juri G. Gelovani

doi:10.1007/s11307-010-0334-9

Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET

Yunming Ying, Pradip Ghosh, Liwei Guo, Ashutosh Pal, Uday Mukhapadhyay, Zhenghong Peng, Hsin Hsien Yeh, Susanna Bertolini, Leo Garcia Flores, Daniel Young, Andrei Volgin, Suren Soghomonyan, William Bornmann, Craig Logsdon, Mian M. Alauddin, Juri G. Gelovani

Brain Research Center

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Abstract

Introduction: Previous studies demonstrated that the lactose-binding protein (hepatocellular carcinoma-intestine-pancreas and pancreatitis-associated proteins (HIP/PAP)) is upregulated >130 times in peritumoral pancreatic tissue as compared to normal pancreatic tissue. Therefore, we developed a new radiolabeled ligand of HIP/PAP, the ethyl-β-d-galactopyranosyl-(1,4′) -2′-deoxy-2′-[¹⁸F]fluoro-β-d-glucopyranoside (Et-[¹⁸F]FDL) for noninvasive imaging of pancreatic carcinoma using positron emission tomography and computerized tomography (PET/CT). Methods: The novel precursor and radiolabeling methods for synthesis of Et-[ ¹⁸F]FDL produced no isomers; the average decay-corrected radiochemical yield was 68%, radiochemical purity >99%, and specific activity >74 GBq/μmol. The radioligand properties of Et-[¹⁸F]FDL were evaluated using an ex vivo autoradiography and immunohistochemistry in pancreatic tissue sections obtained from mice-bearing orthotopic pancreatic tumor xenografts. Results and Discussion: Et-[¹⁸F]FDL binding to peritumoral pancreatic tissue sections strongly correlated with HIP/PAP expression (r = 0.81) and could be completely blocked by treatment with 1 mM lactose. Conclusion: These results suggest that Et-[¹⁸F]FDL is a promising agent which should be evaluated for detection of early pancreatic carcinomas by PET/CT imaging.

Original language	English
Pages (from-to)	536-546
Number of pages	11
Journal	Molecular Imaging and Biology
Volume	13
Issue number	3
DOIs	https://doi.org/10.1007/s11307-010-0334-9
State	Published - Jun 2011

Keywords

Fluorine-18
HIP/PAP protein
Lactose
Pancreatic carcinoma
PET

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Ying, Y., Ghosh, P., Guo, L., Pal, A., Mukhapadhyay, U., Peng, Z., Yeh, H. H., Bertolini, S., Flores, L. G., Young, D., Volgin, A., Soghomonyan, S., Bornmann, W., Logsdon, C., Alauddin, M. M., & Gelovani, J. G. (2011). Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET. Molecular Imaging and Biology, 13(3), 536-546. https://doi.org/10.1007/s11307-010-0334-9

Ying, Yunming ; Ghosh, Pradip ; Guo, Liwei et al. / Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein : Implications for early detection of pancreatic carcinomas with PET. In: Molecular Imaging and Biology. 2011 ; Vol. 13, No. 3. pp. 536-546.

@article{a0476cc9c1f242b883f9bd0ec774005f,

title = "Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[18F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET",

abstract = "Introduction: Previous studies demonstrated that the lactose-binding protein (hepatocellular carcinoma-intestine-pancreas and pancreatitis-associated proteins (HIP/PAP)) is upregulated >130 times in peritumoral pancreatic tissue as compared to normal pancreatic tissue. Therefore, we developed a new radiolabeled ligand of HIP/PAP, the ethyl-β-d-galactopyranosyl-(1,4′) -2′-deoxy-2′-[18F]fluoro-β-d-glucopyranoside (Et-[18F]FDL) for noninvasive imaging of pancreatic carcinoma using positron emission tomography and computerized tomography (PET/CT). Methods: The novel precursor and radiolabeling methods for synthesis of Et-[ 18F]FDL produced no isomers; the average decay-corrected radiochemical yield was 68%, radiochemical purity >99%, and specific activity >74 GBq/μmol. The radioligand properties of Et-[18F]FDL were evaluated using an ex vivo autoradiography and immunohistochemistry in pancreatic tissue sections obtained from mice-bearing orthotopic pancreatic tumor xenografts. Results and Discussion: Et-[18F]FDL binding to peritumoral pancreatic tissue sections strongly correlated with HIP/PAP expression (r = 0.81) and could be completely blocked by treatment with 1 mM lactose. Conclusion: These results suggest that Et-[18F]FDL is a promising agent which should be evaluated for detection of early pancreatic carcinomas by PET/CT imaging.",

keywords = "Fluorine-18, HIP/PAP protein, Lactose, Pancreatic carcinoma, PET",

author = "Yunming Ying and Pradip Ghosh and Liwei Guo and Ashutosh Pal and Uday Mukhapadhyay and Zhenghong Peng and Yeh, {Hsin Hsien} and Susanna Bertolini and Flores, {Leo Garcia} and Daniel Young and Andrei Volgin and Suren Soghomonyan and William Bornmann and Craig Logsdon and Alauddin, {Mian M.} and Gelovani, {Juri G.}",

note = "Funding Information: Acknowledgements. This work was supported by start-up funds of Drs. Juri G. Gelovani and Mian M. Alauddin from The University of Texas, MD, USA, Anderson Cancer Center.",

year = "2011",

month = jun,

doi = "10.1007/s11307-010-0334-9",

language = "English",

volume = "13",

pages = "536--546",

journal = "Molecular Imaging and Biology",

issn = "1536-1632",

publisher = "Springer New York",

number = "3",

}

Ying, Y, Ghosh, P, Guo, L, Pal, A, Mukhapadhyay, U, Peng, Z, Yeh, HH, Bertolini, S, Flores, LG, Young, D, Volgin, A, Soghomonyan, S, Bornmann, W, Logsdon, C, Alauddin, MM & Gelovani, JG 2011, 'Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET', Molecular Imaging and Biology, vol. 13, no. 3, pp. 536-546. https://doi.org/10.1007/s11307-010-0334-9

Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET. / Ying, Yunming; Ghosh, Pradip; Guo, Liwei et al.
In: Molecular Imaging and Biology, Vol. 13, No. 3, 06.2011, p. 536-546.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[18F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein

T2 - Implications for early detection of pancreatic carcinomas with PET

AU - Ying, Yunming

AU - Ghosh, Pradip

AU - Guo, Liwei

AU - Pal, Ashutosh

AU - Mukhapadhyay, Uday

AU - Peng, Zhenghong

AU - Yeh, Hsin Hsien

AU - Bertolini, Susanna

AU - Flores, Leo Garcia

AU - Young, Daniel

AU - Volgin, Andrei

AU - Soghomonyan, Suren

AU - Bornmann, William

AU - Logsdon, Craig

AU - Alauddin, Mian M.

AU - Gelovani, Juri G.

N1 - Funding Information: Acknowledgements. This work was supported by start-up funds of Drs. Juri G. Gelovani and Mian M. Alauddin from The University of Texas, MD, USA, Anderson Cancer Center.

PY - 2011/6

Y1 - 2011/6

N2 - Introduction: Previous studies demonstrated that the lactose-binding protein (hepatocellular carcinoma-intestine-pancreas and pancreatitis-associated proteins (HIP/PAP)) is upregulated >130 times in peritumoral pancreatic tissue as compared to normal pancreatic tissue. Therefore, we developed a new radiolabeled ligand of HIP/PAP, the ethyl-β-d-galactopyranosyl-(1,4′) -2′-deoxy-2′-[18F]fluoro-β-d-glucopyranoside (Et-[18F]FDL) for noninvasive imaging of pancreatic carcinoma using positron emission tomography and computerized tomography (PET/CT). Methods: The novel precursor and radiolabeling methods for synthesis of Et-[ 18F]FDL produced no isomers; the average decay-corrected radiochemical yield was 68%, radiochemical purity >99%, and specific activity >74 GBq/μmol. The radioligand properties of Et-[18F]FDL were evaluated using an ex vivo autoradiography and immunohistochemistry in pancreatic tissue sections obtained from mice-bearing orthotopic pancreatic tumor xenografts. Results and Discussion: Et-[18F]FDL binding to peritumoral pancreatic tissue sections strongly correlated with HIP/PAP expression (r = 0.81) and could be completely blocked by treatment with 1 mM lactose. Conclusion: These results suggest that Et-[18F]FDL is a promising agent which should be evaluated for detection of early pancreatic carcinomas by PET/CT imaging.

AB - Introduction: Previous studies demonstrated that the lactose-binding protein (hepatocellular carcinoma-intestine-pancreas and pancreatitis-associated proteins (HIP/PAP)) is upregulated >130 times in peritumoral pancreatic tissue as compared to normal pancreatic tissue. Therefore, we developed a new radiolabeled ligand of HIP/PAP, the ethyl-β-d-galactopyranosyl-(1,4′) -2′-deoxy-2′-[18F]fluoro-β-d-glucopyranoside (Et-[18F]FDL) for noninvasive imaging of pancreatic carcinoma using positron emission tomography and computerized tomography (PET/CT). Methods: The novel precursor and radiolabeling methods for synthesis of Et-[ 18F]FDL produced no isomers; the average decay-corrected radiochemical yield was 68%, radiochemical purity >99%, and specific activity >74 GBq/μmol. The radioligand properties of Et-[18F]FDL were evaluated using an ex vivo autoradiography and immunohistochemistry in pancreatic tissue sections obtained from mice-bearing orthotopic pancreatic tumor xenografts. Results and Discussion: Et-[18F]FDL binding to peritumoral pancreatic tissue sections strongly correlated with HIP/PAP expression (r = 0.81) and could be completely blocked by treatment with 1 mM lactose. Conclusion: These results suggest that Et-[18F]FDL is a promising agent which should be evaluated for detection of early pancreatic carcinomas by PET/CT imaging.

KW - Fluorine-18

KW - HIP/PAP protein

KW - Lactose

KW - Pancreatic carcinoma

KW - PET

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U2 - 10.1007/s11307-010-0334-9

DO - 10.1007/s11307-010-0334-9

M3 - Article

C2 - 20593279

AN - SCOPUS:79956214563

SN - 1536-1632

VL - 13

SP - 536

EP - 546

JO - Molecular Imaging and Biology

JF - Molecular Imaging and Biology

IS - 3

ER -

Ying Y, Ghosh P, Guo L, Pal A, Mukhapadhyay U, Peng Z et al. Synthesis and ex vivo autoradiographic evaluation of ethyl-β-d- galactopyranosyl-(1,4′)-2′-deoxy-2′-[¹⁸F]fluoro- β-d-glucopyranoside-a novel radioligand for lactose-binding protein: Implications for early detection of pancreatic carcinomas with PET. Molecular Imaging and Biology. 2011 Jun;13(3):536-546. doi: 10.1007/s11307-010-0334-9