6282. Motexafin Lutetium

Nomenclature

CAS number: 246252-04-0; 156436-90-7 (hydrate)
(PB-7-11-233′2′4)-Bis(acetato-κO)[9,10-diethyl-20,21-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,15-dimethyl-8,11-imino-3,6:16,13-dinitrilo-1,18-benzodiazacycloeicosine-5,14-dipropanolato-κN1,κN18,κN23,κN24,κN25]lutetium; 4,5-diethyl-10,23-dimethyl-9,24-bis(3-hydroxypropyl)-16,17-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]pentaazapentacyclo[20.2.1.13,6.18.11. 014,19]heptacosa-1,3,5,7,9,11(27),12,14,16,18,20,22(25),23-tridecaene lutetium(III) complex; lutetium texaphyrin; Lu-Tex; PCI-0123; Antrin (Pharmacyclics); Lutrin (Pharmacyclics); Optrin (Pharmacyclics).
C52H72LuN5O14; mol wt 1166.12.
C 53.56%, H 6.22%, Lu 15.00%, N 6.01%, O 19.21%.

Description and references

Synthetic metal-coordinating expanded porphyrin. Diamagnetic photosensitizer that is activated using far-red light to generate cytotoxic singlet oxygen. Prepn: J. L. Sessler et al., US 5801229 (1998 to Board of Regents Univ. of Texas); S. W. Young et al., Photochem. Photobiol. 63, 892 (1996). Electrochemical characteristics: J. L. Sessler et al., J. Alloys Compd. 249, 146 (1997); and singlet oxygen generation: L. I. Grossweiner et al., Photochem. Photobiol. 70, 138 (1999). LC-MS/MS and ICP-AES determn in plasma: D. Miles et al., AAPS PharmSci. 5, 1 (2003). Preclinical studies in cancer and atheromatous plaque: K. W. Woodburn et al., J. Clin. Laser Med. Surg. 14, 343 (1996); in ocular angiography: M. S. Blumenkranz et al., Am. J. Ophthalmol. 129, 353 (2000). Clinical evaluation in coronary arterial photodynamic therapy: D. J. Kereiakes et al., Circulation 108, 1310 (2003). Review of chemistry and therapeutic potential: T. D. Mody, J. L. Sessler, J. Porphyrins Phthalocyanines 5, 134-142 (2001).

Chemical structure

Properties

Prepd as hydrate, shiny green solid. Sol in water, acetonitrile, methanol, N,N-dimethylformamide. Aqueous solns (100 μM) stable at 2<pH<11 for several months. uv max (methanol): 354, 414, 474, 732 nm (log ε 4.33, 4.67, 5.10, 4.62).

Therapeutic Category

Antiatherosclerotic, antineoplastic (photosensitizer). In treatment of age-related macular degeneration.

Keywords

Antiatherosclerotic; Antineoplastic (Photosensitizer); Macular Degeneration Treatment