1345693-27-7

Basic information

• Product Name: 1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane
• Synonyms: 1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane
• CAS NO: 1345693-27-7
• Molecular Weight: 606.568
• Mol File: 1345693-27-7.mol

Chemical Properties

• CAS DataBase Reference: 1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane(1345693-27-7)
• EPA Substance Registry System: 1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane(1345693-27-7)

Safety Data

• Hazardous Substances Data: 1345693-27-7(Hazardous Substances Data)

Upstream product

• 91983-14-1 2-bromomethylphenylboronic acid 
• 175854-39-4 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 294-90-6 1,4,7,10-tetraazacyclododecan 

Downstream Products

• 1345693-26-6 C₂₇H₄₅BN₄O₂ 
• 1345693-25-5 1-[(2-boronophenyl)methyl]-1,4,7,10-tetraazacyclododecane 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy

Boron neutron capture therapy (BNCT) is a binary therapeutic method for cancer treatment based on the use of a combination of a cancer-specific drug containing boron-10 (10B) and thermal neutron irradiation. For successful BNCT,10B-containing molecules need to accumulate specifically in cancer cells, because destructive effect of the generated heavy particles is limited basically to boron-containing cells. Herein, we report on the design and synthesis of boron compounds that are functionalized with 9-, 12-, and 15-membered macrocyclic polyamines and their Zn2+complexes. Their cytotoxicity, intracellular uptake activity into cancer cells and normal cells, and BNCT effect are also reported. The experimental data suggest that mono- and/or diprotonated forms of metal-free [12]aneN4- and [15]aneN5-type ligands are uptaken into cancer cells, and their complexes with intracellular metals such as Zn2+would induce cell death upon thermal neutron irradiation, possibly via interactions with DNA.

11B NMR sensing of d-block metal ions in vitro and in cells based on the carbon-boron bond cleavage of phenylboronic acid-pendant cyclen (cyclen = 1,4,7,10-tetraazacyclododecane)

Noninvasive magnetic resonance imaging (MRI) including the "chemical shift imaging (CSI)" technique based on 1H NMR signals is a powerful method for the in vivo imaging of intracellular molecules and for monitoring various biological events. However, it has the drawback of low resolution because of background signals from intrinsic water protons. On the other hand, it is assumed that the 11B NMR signals which can be applied to a CSI technique have certain advantages, since boron is an ultratrace element in animal cells and tissues. In this manuscript, we report on the sensing of biologically indispensable d-block metal cations such as zinc, copper, iron, cobalt, manganese, and nickel based on 11B NMR signals of simple phenylboronic acid-pendant cyclen (cyclen = 1,4,7,10- tetraazacyclododecane), L6 and L7, in aqueous solution at physiological pH. The results indicate that the carbon-boron bond of L 6 is cleaved upon the addition of Zn2+ and the broad 11B NMR signal of L6 at 31 ppm is shifted upfield to 19 ppm, which corresponds to the signal of B(OH)3. 1H NMR, X-ray single crystal structure analysis, and UV absorption spectra also provide support for the carbon-boron bond cleavage of ZnL6. Because the cellular uptake of L6 was very small, a more cell-membrane permeable ligand containing the boronic acid ester L7 was synthesized and investigated for the sensing of d-block metal ions using 11B NMR. Data on 11B NMR sensing of Zn2+ in Jurkat T cells using L7 is also presented.