Ir820

Bor was procured from LC Laboratories (Woburn, MA). IR-820, tetraethyl orthosilicate (TEOS), cetyltrimethylammonium bromide (CTAB), ammonium fluoride (NH₄F), coumarin-6, cholesterol (CHO), and CsA were purchased from Sigma-Aldrich (St Louis, MO). 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-distearoyl-sn-glycero-3 phosphoethanolamine-N-[carboxy(polyethylene-glycol)-2000] (DSPE-PEG) were obtained from NOF America Corporation (White Plains, NY) and Avanti Polar Lipid (Alabaster, AL), respectively. LysoTracker red was purchased from Invitrogen/Molecular Probes, Inc. (Eugene, OR). All other chemicals were of reagent grade and used without further purification.

Amino-glucose (85%), IR820, methanol, dimethylsulfoxide and 6-aminohexanoic acid, dimethylformamide were purchased from Sigma–Aldrich. Human thyroid cancer cell line TT was purchased from Cell Bank of Chinese Academy of Sciences (Shanghai). F-12K culture medium, fetal bovine serum (FBS) were purchased from Life technologies. Dulbecco's Phosphate Buffered Saline (DPBS) was purchased from Sigma Aldrich. Abortion measurements were performed using UV– vis spectrophotometer (JH 754PC, Shanghai, China). The high-performance liquid chromatography (HPLC) system (Waters) was used to purify products. Product identification was completed by Q-TOF Micro Mass Spectrometer (Waters). Laser confocal microscopy (Olympus) was used to obtain in vitro fluorescence signal in cells. Fluorescence signal of samples was acquired by NIR spectral system. The home-made NIR imaging system was used for real time detection of fluorescent signal in mice. Briefly, the NIR system contains an excitation laser (λ = 765.9 nm, NL-FC-2.0-763 laser light), a high sensitivity NIR CCD camera (PIXIS 512B, Princeton Instrumentation) and an 800 nm long pass filter for capturing the fluorescence emission from the tissue. In addition, another HLU32F400 808 nm laser (LIMO, Dortmund, Germany) was incorporated as background light to obtain the animal profile.

IR-820 (Sigma Aldrich, Waltham, MA, USA, CAS 172616-80-7) (252 mg; 0.2967 mmol) and p-mercapto-benzoic acid (283 mg; 1.8381 mmol) were reacted in 15 mL of dimethylformamide by following our own methodology [7 (link)], and the title compound was obtained in good yield (99.7 mg).

The following materials were purchased from Sigma-Aldrich (St. Louis, MI): Malic acid, 1,12-dodecanedioic acid (DDA), dimethylsulfoxide (DMSO > 99.9%, reagent grade), pluronic F-127, Dulbecco phosphate-buffered saline (DPBS), phosphate buffered saline (PBS), IR820, penicillin-streptomycin solution, tetrahydrofuran (THF) and trypsin-EDTA. Glycerol was purchased from MP Biomedical (MP Biomedical, LLC, Solon OH). 5-(and-6)-chloromethyl-2′,7′-dichlorodihydrofluorescein diacetate, acetyl ester (CM-H2DCFDA) was purchased from Invitrogen, (Invitrogen, NY), human/mouse total HIF-1 alpha cell-based ELISA and human VEGF quantikine ELISA kit were purchased from R & D systems (R & D Systems, MN).

Camptothecin (CPT), IR-820, 2-hydroxyethyl disulfide (HEDS), 1, 6-hexanediol, triphosgene, 4-nitrophenyl chloroformate, 4-dimethylaminopyridine (DMAP), and other reagents were purchased from Sigma-Aldrich (USA). The solvents anhydrous dimethylformamide (DMF), and anhydrous dichloromethane (DCM) were also acquired from Sigma-Aldrich (USA). Fetal bovine serum (FBS) and Dulbecco’s modified Eagle’s medium (DMEM) were purchased from Gibco. All other reagents and solvents were of analytical or chromatographic grade.