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Synthesis of Bodipy-Labeled Fluorescent Betulinic Acid Derivatives with a Terminal Triphenylphosphonium Group on Side-Chain C-28

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Chemistry of Natural Compounds Aims and scope

A new method for synthesizing BODIPY-labeled betulinic acid derivatives with a terminal mitochondrialtargeting triphenylphosphonium group on side-chain C-28 was developed. The key synthetic step was cross-coupling between C-2 propynyl derivatives of betulinic acid and halides of fluorescent dye derivatives containing an iodo functional group on C-2 or C-8 of the BODIPY platform. The developed procedure for covalent bonding of the BODIPY fluorophore to betulinic acid enables the native 3-OH and 28-COOH groups to be preserved in the triterpene core.

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Acknowledgment

The work was performed in the framework of scientific research plans of the IPC, UFRC, RAS, State Reg. Nos. FMRS-2022-0081 and FMRS-2022-0074 and with financial support from a Stipend of the President of the Russian Federation for Young Scientists and Graduate Students (SP-317.2022.4). Structural studies of synthesized compounds utilized the Agidel′ Common Use Center at UFRC, RAS.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prosp. Oktyabrya, Ufa, 450075, Russia

    A. Yu. Spivak, E. V. Davletshin, R. R. Gubaidullin, A. A. Tukhbatullin & D. A. Nedopekina

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  1. A. Yu. Spivak
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  2. E. V. Davletshin
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  3. R. R. Gubaidullin
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  4. A. A. Tukhbatullin
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  5. D. A. Nedopekina
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Correspondence to A. Yu. Spivak.

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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2022, pp. 893–899.

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Spivak, A.Y., Davletshin, E.V., Gubaidullin, R.R. et al. Synthesis of Bodipy-Labeled Fluorescent Betulinic Acid Derivatives with a Terminal Triphenylphosphonium Group on Side-Chain C-28. Chem Nat Compd 58, 1062–1068 (2022). https://doi.org/10.1007/s10600-022-03869-6

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  • DOI: https://doi.org/10.1007/s10600-022-03869-6

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