<i>N</i>-Aminoacyl-3-amino-<i>nido</i>-carboranes as a Group of Boron-Containing Derivatives of Natural Amino Acids

Gruzdev, Dmitry А.; Telegina, A. A.; Левит, Г. Л.; Краснов, В. П.

doi:10.1021/acs.joc.2c00151

Cited by 19 publications

(7 citation statements)

References 58 publications

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“…Earlier, it was shown that the decapitation of 3-bromo-and 3-iodo-ortho-carboranes proceeds with the retention of the substituent [56]. The retention of a substituent is also characteristic of 3-alkyl-, 3-aryl-, and 3-alkynyl-orthocarboranes [53,[57][58][59][60], as well as of 3-amino-ortho-carborane and other derivatives with a B-N bond [61][62][63][64][65]. At the same time, decapitation of 3-fluoro [66] and 3-hydroxy [67] derivatives of ortho-carborane leads to mixtures of the parent nido-carborane and the corresponding substituted nido-carboranes, i.e., is not selective.…”

Section: Resultsmentioning

confidence: 99%

How to Protect ortho-Carborane from Decapitation—Practical Synthesis of 3,6-Dihalogen Derivatives 3,6-X2-1,2-C2B10H10 (X = Cl, Br, I)

et al. 2022

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The 3-halogen and 3,6-dihalogen derivatives of ortho-carborane 3-X-1,2-C2B10H11 and 3,6-X2-1,2-C2B10H10 (X = Cl, Br, I) were prepared by Cu-assisted halodeboronation of the corresponding pinacolborate derivatives 3-Bpin-1,2-C2B10H11 and 3,6-(Bpin)2-1,2-C2B10H10. It was shown that decapitation of 3-Cl-1,2-C2B10H11, similarly to the corresponding bromo and iodo derivatives, proceeds regioselectively with the retention of the B-Cl bond. Crystal structures of 3,6-Cl2-1,2-C2B10H10 and Cs [3-Cl-7,8-C2B9H11] were determined by single crystal X-ray diffraction.

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Section: Resultsmentioning

confidence: 99%

How to Protect ortho-Carborane from Decapitation—Practical Synthesis of 3,6-Dihalogen Derivatives 3,6-X2-1,2-C2B10H10 (X = Cl, Br, I)

et al. 2022

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“… 44 While no cytotoxic impact was seen in cells that had been exposed to BPA, a modest cytotoxic effect was noted in cells treated with different concentrations of 13 (from 1 to 1 mM) as well as an enhanced cell‐killing effect 13 ‐treated cells when irradiated with thermal neutrons 44 . Gruzdev et al managed to synthesize the nido ‐carboranyl derivatives of natural (S)‐amino acids 14 , 45 successfully varying side chains, including water‐soluble amino acids that were used as a basis for the synthesis of organoboron peptide‐based compounds.…”

Section: Debut Of the New Boron Agent Developed For Bnctmentioning

confidence: 99%

Next generation of boron neutron capture therapy (BNCT) agents for cancer treatment

Coghi

Hosmane

et al. 2023

Medicinal Research Reviews

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Boron neutron capture therapy (BNCT) is one of the most promising treatments among neutron capture therapies due to its long‐term clinical application and unequivocally obtained success during clinical trials. Boron drug and neutron play an equivalent crucial role in BNCT. Nevertheless, current clinically used l‐boronophenylalanine (BPA) and sodium borocaptate (BSH) suffer from large uptake dose and low blood to tumor selectivity, and that initiated overwhelm screening of next generation of BNCT agents. Various boron agents, such as small molecules and macro/nano‐vehicles, have been explored with better success. In this featured article, different types of agents are rationally analyzed and compared, and the feasible targets are shared to present a perspective view for the future of BNCT in cancer treatment. This review aims at summarizing the current knowledge of a variety of boron compounds, reported recently, for the application of BCNT.

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“…In this regard, the development of synthetic approaches to new carboranyl derivatives of amino acids is of considerable interest. Previously, we have obtained a series of carboranyl derivatives of natural amino acids containing a 3-amino- closo - o -carborane residue as well as planar-chiral closo - and nido -carborane-based amino acids …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Charge-Compensated nido-Carboranyl Derivatives of Sulfur-Containing Amino Acids and Biotin

Gruzdev,

Telegina,

Levit

et al. 2023

J. Org. Chem.

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A new group of charge-compensated nido-carboranyl derivatives of sulfur-containing amino acids and biotin has been synthesized in which the boron atom in position 9 or 10 of carborane is attached to a positively charged sulfur atom. The possibilities of obtaining symmetrical B(10)-substituted and asymmetric B(9)-substituted nido-carboranes were studied. Using the example of (S)-methionine and D-biotin derivatives, water-soluble S-substituted charge-compensated nido-carboranes with free functional groups were prepared. The results obtained open up prospects for the development of potential boron delivery agents for BNCT as well as new bioactive compounds containing a negatively charged nido-carboranyl fragment bearing a positive charge on the sulfur atom associated with the boron cluster.

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N-Aminoacyl-3-amino-nido-carboranes as a Group of Boron-Containing Derivatives of Natural Amino Acids

Abstract: Figure 1. Main concepts of carboranyl amino acid derivatives. Note pubs.acs.org/joc

Cited by 19 publications

References 58 publications

How to Protect ortho-Carborane from Decapitation—Practical Synthesis of 3,6-Dihalogen Derivatives 3,6-X2-1,2-C2B10H10 (X = Cl, Br, I)

How to Protect ortho-Carborane from Decapitation—Practical Synthesis of 3,6-Dihalogen Derivatives 3,6-X2-1,2-C2B10H10 (X = Cl, Br, I)

Next generation of boron neutron capture therapy (BNCT) agents for cancer treatment

Synthesis of Charge-Compensated nido-Carboranyl Derivatives of Sulfur-Containing Amino Acids and Biotin

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