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, Ke-Ke; Wei, Di; He, Wei; Yuan, Jian

doi:10.3892/ijo.2016.3693

Cited by 15 publications

(13 citation statements)

References 29 publications

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“…We choose this dye because it emits in the near infrared and can be easily detected by the in vivo imaging systems (IVIS), also avoiding background noise caused by the mouse's own autofluorescence. 76 When tumors reached a size of 0.5 cm 3 , 100 μL of O 2 LNC-i780, and αCD44-O 2 LNC-i780 were administered in the tail vein of the mice in a single dose. After one week, the mice were analyzed, euthanized, and the tumors were removed as well as all the organs.…”

Section: Lnc Sample (Figures S5−s15)supporting

confidence: 89%

Anti-CD44-Conjugated Olive Oil Liquid Nanocapsules for Targeting Pancreatic Cancer Stem Cells

et al. 2021

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The latest trends in cancer research and nanomedicine focus on using nanocarriers to target cancer stem cells (CSCs). Specifically, lipid liquid nanocapsules are usually developed as nanocarriers for lipophilic drug delivery. Here, we developed olive oil liquid NCs (O2LNCs) functionalized by covalent coupling of an anti-CD44-fluorescein isothiocyanate antibody (αCD44). First, O2LNCs are formed by a core of olive oil surrounded by a shell containing phospholipids, a nonionic surfactant, and deoxycholic acid molecules. Then, O2LNCs were coated with an αCD44 antibody (αCD44-O2LNC). The optimization of an αCD44 coating procedure, a complete physicochemical characterization, as well as clear evidence of their efficacy in vitro and in vivo were demonstrated. Our results indicate the high targeted uptake of these αCD44-O2LNCs, and the increased antitumor efficacy (up to four times) of paclitaxel-loaded-αCD44-O2LNC compared to free paclitaxel in pancreatic CSCs (PCSCs). Also, αCD44-O2LNCs were able to selectively target PCSCs in an orthotopic xenotransplant in vivo model.

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Section: Lnc Sample (Figures S5−s15)supporting

confidence: 89%

Anti-CD44-Conjugated Olive Oil Liquid Nanocapsules for Targeting Pancreatic Cancer Stem Cells

et al. 2021

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“…The 7-OH MOM-protected genistein was then selectively conjugated through the 4′-OH with IR 783. HCD, IR 783 is known to have high affinity with cancer cells and is now under extensive investigation from mechanistic to drug-carrying abilities [21,22,31,36,44]. As shown in Scheme 1 the desired conjugate was obtained as single isomer upon MOM group deprotection and characterized by 1 H-NMR and mass spectrometry for the chemical composition (see Supplementary Materials).…”

Section: Discussionmentioning

confidence: 99%

“…We recently demonstrated that radiolabeled cyanine dye molecules can be used to detect and diagnose cancer lesions [24,25]. Additional reports of cancer cell-specific delivery and targeting of drug-cyanine dye conjugates to tumors have been described by us and other laboratories [26,27,28,29,30,31,32]. Considering ongoing research on genistein in our laboratory [33], we sought to improve its therapeutic potential by conjugating it with a cyanine dye.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Genistein-IR783 Conjugate: Cancer Cell Targeted Delivery in MCF-7 for Superior Anti-Cancer Therapy

et al. 2019

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The flavonoid-based natural product genistein is a biologically active compound possessing promising anti-oxidant and anti-cancer properties. Poor pharmacokinetics along with low potency limit however the therapeutic application of genistein in cancer therapy. In order to overcome those limitations and to expand its therapeutic window of efficacy, we sought to covalently attach genistein with a heptamethine cyanine dye—IR 783—for cancer cell targeting and enhanced delivery to tumors. Herein we report the synthesis, a selective detailed characterization and preliminary in vitro/in vivo biological evaluation of genistein-IR 783 conjugate 4. The conjugate 4 displayed improved potency against human breast cancer MCF-7 cells (10.4 ± 1.0 μM) as compared with the parent genistein (24.8 ± 0.5 μM) or IR 783 (25.7 ± 0.7 μM) and exhibited selective high uptake in MCF-7 as against the normal mammary gland MCF-10A cells in various assays. In the cell viability assay, conjugate 4 exhibited over threefold lower potency against MCF-10A cells (32.1 ± 1.1 μM) suggesting that the anti-cancer profile of parent genistein is significantly improved upon conjugation with the dye IR783. Furthermore, the genistein-IR783 conjugate 4 was shown to be especially accumulated in MCF-7 cancer cells by fluorescent intensity measurements and inverted fluorescence microscopy in fixed cells as well as in live cells with time via live cell confocal fluorescence imaging. The mechanism-based uptake inhibition of conjugate 4 was observed with OATPs inhibitor BSP and in part with amiloride, as a macropinocytosis inhibitor. For the first time we have shown amiloride inhibited uptake of cyanine dye by about ~40%. Finally, genistein-IR 783 conjugate 4 was shown to be localized in MCF-7 tumor xenografts of mice breast cancer model via in vivo near infrared fluorescence (NIRF) imaging. In conclusion, conjugation of genistein with cyanine dye IR783 indeed improved its pharmacological profile by cancer cell selective uptake and targeting and therefore warrants further investigations as a new anti-cancer therapeutics derived from natural product genistein.

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“…In particular, this dye is known to selectively accumulate in cancer cells and has been used to discriminate between tumor lesions from normal tissues (Zhang et al, 2014). Yi et al recently described on a novel IR780-abiraterone conjugate ( 2 , Figure 3) for the concomitant imaging and therapy of PC both in vitro and in vivo (Yi et al, 2016).…”

Section: Molecular Conjugates For Pdt-mediated Pc Treatmentmentioning

confidence: 99%

Light-Induced Therapies for Prostate Cancer Treatment

et al. 2019

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Prostate cancer (PC) is one of the most widespread tumors affecting the urinary system and the fifth-leading cause from cancer death in men worldwide. Despite PC mortality rates have been decreasing during the last years, most likely due to an intensification of early diagnosis, still more than 300,000 men die each year because of this disease. In this view, researchers in all countries are engaged in finding new ways to tackle PC, including the design and synthesis of novel molecular and macromolecular entities able to challenge different PC biological targets, while limiting the extent of unwanted side effects that significantly limit men's life quality. Among this field of research, photo-induced therapies, such as photodynamic and photothermal therapies (PDT and PTT), might represent an important advancement in PC treatment due to their extremely localized and controlled cytotoxic effect, as well as their low incidence of side effects and tumor resistance occurrence. Based on these considerations, this review aims to gather and discuss the last 5-years literature reports dealing with the synthesis and biological activity of molecular conjugates and nano-platforms for photo-induced therapies as co-adjuvant or combined therapeutic modalities for the treatment of localized PC.

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

Cited by 15 publications

References 29 publications

Anti-CD44-Conjugated Olive Oil Liquid Nanocapsules for Targeting Pancreatic Cancer Stem Cells

Anti-CD44-Conjugated Olive Oil Liquid Nanocapsules for Targeting Pancreatic Cancer Stem Cells

Synthesis and Biological Evaluation of Genistein-IR783 Conjugate: Cancer Cell Targeted Delivery in MCF-7 for Superior Anti-Cancer Therapy

Light-Induced Therapies for Prostate Cancer Treatment

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