Optimization of the Procedure for Gram Scale Synthesis of Silicon Rhodamine and its Application in Labeling BRD4 Kinase Inhibitor

Fu M, Xiao Y, Qian X, Zhao D, Xu Y. A design concept of long-wavelength fluorescent analogs of rhodamine dyes: replacement of oxygen with silicon atom. Chem Commun (Camb). 2008;15:1780–2.

Article  Google Scholar 

Ahn SH, Thach D, Vaughn BA, Alford VM, Preston AN, Laughlin ST, Boros E. Linear desferrichrome-linked silicon-rhodamine antibody conjugate enables targeted multimodal imaging of HER2 in vitro and in vivo. Mol Pharm. 2019;16(3):1412–20.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kushida Y, Nagano T, Hanaoka K. Silicon-substituted xanthene dyes and their applications in bioimaging. Analyst. 2015;140(3):685–95.

Article  CAS  PubMed  Google Scholar 

Mao Z, Jiang H, Song X, Hu W, Liu Z. Development of a silicon-rhodamine based near-infrared emissive two-photon fluorescent probe for nitric oxide. Anal Chem. 2017;89(18):9620–4.

Article  CAS  PubMed  Google Scholar 

Frei MS, Hoess P, Lampe M, Nijmeijer B, Kueblbeck M, Ellenberg J, Wadepohl H, Ries J, Pitsch S, Reymond L, Johnsson K. Photoactivation of silicon rhodamines via a light-induced protonation. Nat Commun. 2019;10(1):4580.

Article  PubMed  PubMed Central  Google Scholar 

Wang L, Frei MS, Salim A, Johnsson K. Small-molecule fluorescent probes for live-cell super-resolution microscopy. J Am Chem Soc. 2019;141(7):2770–81.

Article  CAS  PubMed  Google Scholar 

Chyan W, Raines RT. Enzyme-activated fluorogenic probes for live-cell and in vivo imaging. ACS Chem Biol. 2018;13(7):1810–23.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Lardon N, Wang L, Tschanz A, Hoess P, Tran M, D’Este E, Ries J, Johnsson K. Systematic tuning of rhodamine spirocyclization for super-resolution microscopy. J Am Chem Soc. 2021;143(36):14592–600.

Article  CAS  PubMed  Google Scholar 

Ortiz G, Liu P, Deal PE, Nensel AK, Martinez KN, Shamardani K, Adesnik H, Miller EW. A silicon-rhodamine chemical-genetic hybrid for far red voltage imaging from defined neurons in brain slice. RSC Chem Biol. 2021;2(6):1594–9.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Lukinavičius G, Reymond L, D’Este E, Masharina A, Göttfert F, Ta H, Güther A, Fournier M, Rizzo S, Waldmann H, Blaukopf C, Sommer C, Gerlich DW, Arndt HD, Hell SW, Johnsson K. Fluorogenic probes for live-cell imaging of the cytoskeleton. Nat Methods. 2014;11(7):731–3.

Article  PubMed  Google Scholar 

Karch S, Broichhagen J, Schneider J, Böning D, Hartmann S, Schmid B, Tripal P, Palmisano R, Alzheimer C, Johnsson K, Huth T. A new fluorogenic small-molecule labeling tool for surface diffusion analysis and advanced fluorescence imaging of β-Site amyloid precursor protein-cleaving enzyme 1 based on silicone rhodamine: SiR-BACE1. J Med Chem. 2018;61(14):6121–39.

Article  CAS  PubMed  Google Scholar 

Lukinavičius G, Blaukopf C, Pershagen E, Schena A, Reymond L, Derivery E, Gonzalez-Gaitan M, D’Este E, Hell SW, Wolfram Gerlich D, Johnsson K. SiR-Hoechst is a far-red DNA stain for live-cell nanoscopy. Nat Commun. 2015;6:8497.

Article  PubMed  Google Scholar 

Brandes B, Hoenke S, Fischer L, Csuk R. Design, synthesis and cytotoxicity of BODIPY FL labelled triterpenoids. Eur J Med Chem. 2020;185:111858.

Article  CAS  PubMed  Google Scholar 

Zhu PJ, Yu ZZ, Lv YF, Zhao JL, Tong YY, You QD, Jiang ZY. Discovery of 3,5-Dimethyl-4-Sulfonyl-1H-Pyrrole-based myeloid cell leukemia 1 inhibitors with high affinity, selectivity, and oral bioavailability. J Med Chem. 2021;64(15):11330–53.

Article  CAS  PubMed  Google Scholar 

Butkevich AN. Modular synthetic approach to silicon-rhodamine homologues and analogues via bis-aryllanthanum reagents. Org Lett. 2021;23(7):2604–9.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Matthias J, Kanagasundaram T, Kopka K, Kramer CS. Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement. Beilstein J Org Chem. 2019;15:2333–43.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Grimm JB, Brown TA, Tkachuk AN, Lavis LD. General synthetic method for Si-fluoresceins and Si-rhodamines. ACS Cent Sci. 2017;3(9):975–85.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Xiao Y, Qian XH. Substitution of oxygen with silicon: a big step forward for—fluorescent dyes in life science. Coord Chem Rev. 2020;423:213513.

Article  CAS  Google Scholar 

Wang B, Chai X, Zhu W, Wang T, Wu Q. A general approach to spirolactonized Si-rhodamines. Chem Commun (Camb). 2014;50(92):14374–7.

Article  CAS  PubMed  Google Scholar 

Gao J, Hou B, Zhu Q, Yang L, Jiang X, Zou Z, Li X, Xu T, Zheng M, Chen YH, Xu Z, Xu H, Yu H. Engineered bioorthogonal POLY-PROTAC nanoparticles for tumour-specific protein degradation and precise cancer therapy. Nat Commun. 2022;13(1):4318.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Majumder R, Mandal M. Screening of plant-based natural compounds as a potential COVID-19 main protease inhibitor: an in silico docking and molecular dynamics simulation approach. J Biomol Struct Dyn. 2022;40(2):696–711.

Article  CAS  PubMed  Google Scholar 

Jin Y, Fan J, Wang R, Wang X, Li N, You Q, Jiang Z. Ligation to scavenging strategy enables on-demand termination of targeted protein degradation. J Am Chem Soc. 2023;145(13):7218–29.

Article  CAS  PubMed  Google Scholar 

Dooley KE, Warburton A, McBride AA. Tandemly integrated HPV16 can form a BRD4-dependent super-enhancer-like element that drives transcription of viral oncogenes. Mbio. 2016;7(5):e01446-16.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Donati B, Lorenzini E, Ciarrocchi A. Brd4 and cancer: going beyond transcriptional regulation. Mol Cancer. 2018;17(1):164.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Wu Y, Wang Y, Diao P, Zhang W, Li J, Ge H, Song Y, Li Z, Wang D, Liu L, Jiang H, Cheng J. Therapeutic targeting of BRD4 in head neck squamous cell carcinoma. Theranostics. 2019;9(6):1777–93.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Liao X, Qian X, Zhang Z, Tao Y, Li Z, Zhang Q, Liang H, Li X, Xie Y, Zhuo R, Chen Y, Jiang Y, Cao H, Niu J, Xue C, Ni J, Pan J, Cui D. ARV-825 demonstrates antitumor activity in gastric cancer via MYC-targets and G2M-checkpoint signaling pathways. Front Oncol. 2021;11:753119.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Wu SY, Lee CF, Lai HT, Yu CT, Lee JE, Zuo H, Tsai SY, Tsai MJ, Ge K, Wan Y, Chiang CM. Opposing functions of BRD4 isoforms in breast cancer. Mol Cell. 2020;78(6):1114–1132.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Liu J, Duan Z, Guo W, Zeng L, Wu Y, Chen Y, Tai F, Wang Y, Lin Y, Zhang Q, He Y, Deng J, Stewart RL, Wang C, Lin PC, Ghaffari S, Evers BM, Liu S, Zhou MM, Zhou BP, Shi J. Targeting the BRD4/FOXO3a/CDK6 axis sensitizes AKT inhibition in luminal breast cancer. Nat Commun. 2018;9(1):5200.

Article  PubMed  PubMed Central  Google Scholar 

Grimm JB, English BP, Chen J, Slaughter JP, Zhang Z, Revyakin A, Patel R, Macklin JJ, Normanno D, Singer RH, Lionnet T, Lavis LD. A general method to improve fluorophores for live-cell and single-molecule microscopy. Nat Methods. 2015;12(3):244–50.

Article  CAS 

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