Synthesis of Sugar–Boronic Acid Derivatives: A Class of Potential Agents for Boron Neutron Capture Therapy

Imperio, Daniela; Grosso, Erika Del; Fallarini, Silvia; Lombardi, Grazia; Panza, Luigi

doi:10.1021/acs.orglett.7b00382

Cited by 18 publications

(17 citation statements)

References 28 publications

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“…Furthermore, the Boc-protected derivatives, e.g., TB-6-BT ( 5 ), TB-5-BT ( 1 ), and DBA-5-BT 2 , are slightly toxic against 3T3 cells but insignificant when compared with the control compound BPA. BPA was generally regarded as nontoxic. − …”

Section: Resultsmentioning

confidence: 99%

Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy

Chio

Huang

Chou

et al. 2020

ACS Med. Chem. Lett.

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Boron neutron capture therapy (BNCT) is a binary therapeutic approach. Nonradioactive boron-10 atoms accumulated in tumor cells combining with the neutron beams produce two highly energetic particles that could eradicate the cell that takes it and the neighboring cells. Small molecules that carry boron atom, e.g. 5- and 6-boronated and 2,7-diboronated tryptophans, were assessed for their boron accumulation in U87-MG, LN229, and 3T3 for BNCT. TriBoc tryptophan, TB-6-BT, shows boron-10 at 300 ppm in both types of tumor cells with a tumor to normal ratio (T/N) of 5.19–5.25 (4 h). TB-5-BT and DBA-5-BT show boron-10 at 300 ppm (2 h) in U87-MG cells. TB-5-BT exerts a T/N of >9.66 (1 h) in LN229 compared with the current clinical boronophenyl alanine with a highest T/N of 2.3 (1 h) and accumulation concentration of <50 ppm. TB-5-BT and TB-6-BT warrant further animal study.

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Section: Resultsmentioning

confidence: 99%

Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy

Chio

Huang

Chou

et al. 2020

ACS Med. Chem. Lett.

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“…Notably, the formation of similar vinyl furanosides was also observed by Imperio et al during their synthesis of 6C-boronic acid sugar derivatives. 95 Introducing a silicon substituent at the 4-position of a carbohydrate scaffold was overall a challenging feat and though we succeeded the reactivity study was not performed on a fully functionalized sugar scaffold.…”

Section: Account Synlettmentioning

confidence: 99%

Silylated Sugars – Synthesis and Properties

Bols

Frihed

Pedersen

et al. 2021

Synlett

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Silicon has been used in carbohydrate chemistry for half a century, but mostly as a protective group for sugar alcohols. Recently, the use of silicon has expanded to functionalization via C–H activation, conformational arming of glycosyl donors, and conformational alteration of carbohydrates. Silicon has proven useful as more than a protective group and during the last one and a half decades we have demonstrated how it influences both the reactivity of glycosyl donors and stereochemical outcome of glycosylations. Silicon can also be attached directly to the sugar C-backbone, which has even more pronounced effects on the chemistry and properties of the molecules. In this Account, we will give a tour through our work involving silicon and carbohydrates.1 Introduction2 Conformational Arming of Glycosyl Donors with Silyl Groups3 Silyl Protective Groups for Tethering Glycosyl Donors4. Si–C Glycosides via C–H Activation4.1 C–H Activation and Oxidation of Methyl 6-Deoxy-l-glycosides4.2 Synthesis of All Eight 6-Deoxy-l-sugars4.3 Synthesis of All Eight l-Sugars by C–H Activation4.4 Modification of the Oxasilolane Ring5 C–Si in Glycosyl Donors – Activating or Not?6 Si–C-Substituted Pyranosides7 Perspective

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“…It is noteworthy that the formation of vinyl furanosides also was observed by Imperio et al during their synthesis of 6-boronic acid sugar derivatives. [45] The similarity in side-product formation reveals a reduced stability of polyols containing weaker electronegative elements, both in terms of acid and base lability.…”

Section: Entrymentioning

confidence: 99%

Reactivity, Selectivity, and Synthesis of 4‐C‐Silylated Glycosyl Donors and 4‐Deoxy Analogues

Pedersen

2020

Angewandte Chemie

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A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared with the 4‐deoxy variant, it was found that the anomeric selectivity was influenced more by the C‐2 substituents orientation than the silyl in the 4‐position. In general, the reactivity of these donors was higher than the corresponding 4‐deoxy‐analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two.

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Synthesis of Sugar–Boronic Acid Derivatives: A Class of Potential Agents for Boron Neutron Capture Therapy

Cited by 18 publications

References 28 publications

Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy

Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy

Silylated Sugars – Synthesis and Properties

Reactivity, Selectivity, and Synthesis of 4‐C‐Silylated Glycosyl Donors and 4‐Deoxy Analogues

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