Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

Abstract

Bromide (CTAB), and Zinc phthalocyanine were obtained from TCI Chemicals. NMR solvents were purchased from Cambridge Isotope Laboratories, Inc. Epithelioid cervix carcinoma HeLa and lung adenocarcinoma A549 cell lines and normal human embryonic kidney (HEK293) cell line were acquired from The National Centre for Cell Science, India. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide (MTT), Dulbecco's modified eagle medium (DMEM), Trypsin EDTA mixture, Fetal Bovine Serum (FBS), and Antibiotic Antimycotic Solution were obtained from Himedia. MitoTracker Green was procured from Thermo Fisher Scientific. METHODS Microwave Synthesizer: Unsymmetrical MSQ and MSQRot were constructed using microwave synthesizer (CEM corporation, USA make, model discover bio). NMR Spectroscopy: 1D (1 H, 13 C, 31 P) and 2D NMR (1 H-1 H DQF COSY) were measured on Bruker DPX500 MHz, Bruker DPX400 MHz, and Bruker DPX300 MHz spectrometers at 25C in appropriate deuterated solvents. HRMS (ESI): High-resolution electrospray ionisation mass spectrometry (HRMS-ESI) was recorded using a Q-Tofmicro TM (Waters Corporation) mass spectrometer. Single Crystal X-Ray Diffraction: Single crystals suitable for X-ray diffraction was obtained by vapor diffusion method. A solution of SQRot in CHCl 3 was placed in a 2 mL vial and put inside a 20 mL vial filled with EtOAc. The larger vial was capped and allow to slow diffusion of EtOAc into CHCl 3 solution of the compound. Diffraction data of SQRot was measured with MoK α radiation (a graded multilayer mirror monochromator, λ = 0.71073 Å) at 273 K on a micro focus Single Crystal X-ray Diffraction instrument (Make: Bruker, Model : D8 Quest). A PHOTON-100 CMOS detector is used. Structures were solved by direct methods using the SHELXT 2014/5 program. S1,S2 Refinements were carried out with a full-matrix least squares method against F 2 using SHELXL-2018/3 S1,S2 incorporated in Olex2 S3 crystallographic collective package. The non-hydrogen atoms were refined with anisotropic thermal parameters. Formula sum = C97.24 H84 N6 O12, formula weight = 1528.58, crystal system = triclinic, space group = P-1, a = 11.1202(11) Å, b = 11.6727(12) Å, c = 16.8575(17) Å,  = 94.197(3),  = 100.651(3),  = 111.900(3), V = 1970.9(3) Å 3 , Z = 1, D calcd = 1.288 g cm 3 , μ = 0.085 mm 1. The final R value was R 1 = 0.0688 and wR 2 = 0.1875 for reflections with I > 2ζ(I).

Vanillin Benzothiazole Derivative Reduces Cellular Reactive Oxygen Species and Detects Amyloid Fibrillar Aggregates in Alzheimer’s Disease Brain

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Viscosity probes towards different organelles with red emission based on an identical hemicyanine structure

“…As a D-π-A type molecular rotor, the fluorescent parent displayed high sensitivity to viscosity. Regarding compound 5-carboxy-2-(4-(diethylamino) styryl)-1,3,3-trimethyl-3H-indol-1-ium, there have been some reports in organic synthesis, 23,24 but its ability to modify and target as a probe has not been clearly studied. In this paper, using condensation reactions, four fluorescent probes 1a-d with the D-π-A structure as the main skeleton were synthesized (Scheme 1).…”

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