Boronophenylalanine B-10

Boronophenylalanine B-10 Property

Melting point:

285-298 °C (decomp)(Solv: water (7732-18-5))

Density 

1.347±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

storage temp. 

Store at -20°C

solubility 

DMSO: Insoluble;Ethanol: Insoluble

form 

Solid

color 

White to off-white

Water Solubility 

Water: Insoluble

InChI

InChI=1S/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1/i10-1

InChIKey

NFIVJOSXJDORSP-ULMHTEDTSA-N

SMILES

C(C1C=CC(=CC=1)[10B](O)O)[C@H](N)C(=O)O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Boronophenylalanine B-10 Chemical Properties,Usage,Production

Description

Boronophenylalanine B-10 is a boronophenylalanine and boron (boron-10) carrier for boron neutron capture therapy (BNCT) with potential anti-tumour activity. Upon administration, boron flange (10B) is mainly taken up by tumour cells. When irradiated with neutrons, boron flange (10B) absorbs neutrons and self-destructs, releasing short-range alpha radiation and "recoil" lithium in the tumour cells, leading to alpha radiation-induced tumour cell death. This highly selective local radio-targeting of tumour cells spares adjacent normal tissue.

Uses

Borofalan (10B) should be used in combination with BNCT for the treatment of patients with unresectable, locally advanced or locally recurrent head and neck cancer.

Synthesis

The starting material for the synthesis of Borofalan (10B) starts with (S)-N-Boc-4-iodophenylalanine (compound 230), which is easily obtained by Boc protection of (S)-4-iodophenylalanine (compound 229). Next, borylation is performed via a metal-halogen exchange reaction. After borylation, the reaction is quenched using tributyl borate. Finally, a Boc deprotection step is performed to obtain the final Borofalan (10B).