Synthesis of IR-780 dye-conjugated abiraterone for prostate cancer imaging and therapy

Xiaomin Yi, Jingfang Zhang, Fei Yan, Zifan Lu, Jiaoti Huang, Chong-Xian Pan, Jiarui Yuan, Wanxiang Zheng, Keke Zhang, Di Wei, Wei He, Jianlin Yuan

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Near-infrared fluorescence (NIRF) imaging is a novel imaging modality that allows for detection and real-time monitoring of various pathophysiological states. IR-780 iodide has been used as an ideal platform to construct theranostic agents for cancer imaging and therapy. Abiraterone is a 17α-hydroxylase/C17, 20-lyase (CYP17) inhibitor that has been approved for use in patients with prostate cancer after androgen deprivation therapy. We report the synthesis and characterization of IR-780 conjugated abiraterone for the dual purpose of prostate cancer imaging and therapy. The new compound Abi-780 retained the excellent photophysical characteristics and NIRF imaging property of IR-780 dye. Abi-780 preferentially accumulated in plasmonic organelles of prostate cancer cells but not in normal prostate epithelial cells. Dose-dependent inhibition of cultured prostate cancer cells by Abi-780 was found. Abi-780 at 20 μM significantly reduced the capabilities of colony formation and migration/invasion potential as well as increasing the apoptosis rate of prostate cancer cells. NIRF imaging using Abi-780 selectively identified the tumors in mice bearing prostate cancer xenografts. Moreover, Abi-780 treatment significantly retarded the tumor growth. No severe systemic toxicity was observed in mice with daily injection of high-dose Abi-780 for one month. In conclusion, biocompatible Abi-780 is highly effective both in prostate cancer imaging and therapy. Constructing theranostic agents using the NIRF dye platform holds great promise in accurate diagnosis and targeted treatment of cancer.

Original languageEnglish (US)
Pages (from-to)1911-1920
Number of pages10
JournalInternational Journal of Oncology
Volume49
Issue number5
DOIs
StatePublished - Nov 1 2016

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Prostatic Neoplasms
Coloring Agents
Optical Imaging
Therapeutics
Neoplasms
Steroid 17-alpha-Hydroxylase
Lyases
Iodides
Mixed Function Oxygenases
2-(2-(2-chloro-3-((1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene)-1-cyclohexen-1-yl)ethenyl)-3,3-dimethyl-1-propylindolium
abiraterone
Heterografts
Organelles
Androgens
Prostate
Fluorescence
Epithelial Cells
Apoptosis
Injections
Growth

Keywords

  • Abiraterone
  • Bio-conjugation
  • Fluorescence imaging
  • IR-780
  • Near-infrared fluorescence dye
  • Prostate cancer

ASJC Scopus subject areas

  • Oncology
  • Cancer Research

Cite this

Synthesis of IR-780 dye-conjugated abiraterone for prostate cancer imaging and therapy. / Yi, Xiaomin; Zhang, Jingfang; Yan, Fei; Lu, Zifan; Huang, Jiaoti; Pan, Chong-Xian; Yuan, Jiarui; Zheng, Wanxiang; Zhang, Keke; Wei, Di; He, Wei; Yuan, Jianlin.

In: International Journal of Oncology, Vol. 49, No. 5, 01.11.2016, p. 1911-1920.

Research output: Contribution to journalArticle

Yi, X, Zhang, J, Yan, F, Lu, Z, Huang, J, Pan, C-X, Yuan, J, Zheng, W, Zhang, K, Wei, D, He, W & Yuan, J 2016, 'Synthesis of IR-780 dye-conjugated abiraterone for prostate cancer imaging and therapy', International Journal of Oncology, vol. 49, no. 5, pp. 1911-1920. https://doi.org/10.3892/ijo.2016.3693
Yi, Xiaomin ; Zhang, Jingfang ; Yan, Fei ; Lu, Zifan ; Huang, Jiaoti ; Pan, Chong-Xian ; Yuan, Jiarui ; Zheng, Wanxiang ; Zhang, Keke ; Wei, Di ; He, Wei ; Yuan, Jianlin. / Synthesis of IR-780 dye-conjugated abiraterone for prostate cancer imaging and therapy. In: International Journal of Oncology. 2016 ; Vol. 49, No. 5. pp. 1911-1920.
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AU - Huang, Jiaoti

AU - Pan, Chong-Xian

AU - Yuan, Jiarui

AU - Zheng, Wanxiang

AU - Zhang, Keke

AU - Wei, Di

AU - He, Wei

AU - Yuan, Jianlin

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AB - Near-infrared fluorescence (NIRF) imaging is a novel imaging modality that allows for detection and real-time monitoring of various pathophysiological states. IR-780 iodide has been used as an ideal platform to construct theranostic agents for cancer imaging and therapy. Abiraterone is a 17α-hydroxylase/C17, 20-lyase (CYP17) inhibitor that has been approved for use in patients with prostate cancer after androgen deprivation therapy. We report the synthesis and characterization of IR-780 conjugated abiraterone for the dual purpose of prostate cancer imaging and therapy. The new compound Abi-780 retained the excellent photophysical characteristics and NIRF imaging property of IR-780 dye. Abi-780 preferentially accumulated in plasmonic organelles of prostate cancer cells but not in normal prostate epithelial cells. Dose-dependent inhibition of cultured prostate cancer cells by Abi-780 was found. Abi-780 at 20 μM significantly reduced the capabilities of colony formation and migration/invasion potential as well as increasing the apoptosis rate of prostate cancer cells. NIRF imaging using Abi-780 selectively identified the tumors in mice bearing prostate cancer xenografts. Moreover, Abi-780 treatment significantly retarded the tumor growth. No severe systemic toxicity was observed in mice with daily injection of high-dose Abi-780 for one month. In conclusion, biocompatible Abi-780 is highly effective both in prostate cancer imaging and therapy. Constructing theranostic agents using the NIRF dye platform holds great promise in accurate diagnosis and targeted treatment of cancer.

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