6281. Motexafin Gadolinium

Nomenclature

CAS number: 246252-06-2; 156436-89-4 (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]gadolinium; 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 gadolinium(III) complex; gadolinium texaphyrin; Gd-Tex; Gd-T2BET; NSC-695238; PCI-0120; Xcytrin (Pharmacyclics).
C52H72GdN5O14; mol wt 1148.40.
C 54.38%, H 6.32%, Gd 13.69%, N 6.10%, O 19.50%.

Description and references

Synthetic metal-coordinating expanded porphyrin. Paramagnetic redox mediator and radiation enhancer. Prepn: J. L. Sessler et al., US 5801229 (1998 to Board of Regents Univ. of Texas); and redox chemistry: J. L. Sessler et al., J. Phys. Chem. A 103, 787 (1999). Tumor selective radiosensitizing activity and MRI characteristics: S. W. Young et al., Proc. Natl. Acad. Sci. USA 93, 6610 (1996). HPLC determn in plasma: R. A. Parise et al., J. Chromatogr. B 749, 145 (2000). Mechanism of action study: D. Magda et al., Int. J. Radiat. Oncol. Biol. Phys. 51, 1025 (2001); S. I. Hashemy et al., J. Biol. Chem. 281, 10691 (2006). Clinical pharmacokinetics: D. I. Rosenthal et al., Clin. Cancer Res. 5, 739 (1999). Clinical evaluation with radiation in brain metastases: M. P. Mehta et al., J. Clin. Oncol. 20, 3445 (2002); C. A. Meyers et al., J. Clin. Oncol. 22, 157 (2004). Review of chemistry: T. D. Mody, J. L. Sessler, J. Porphyrins Phthalocyanines 5, 134-142 (2001); of therapeutic potential in brain tumors: D. Khuntia, M. Mehta, Expert Rev. Anticancer Ther. 4, 981-989 (2004).

Chemical structure

Properties

Prepd as hemihydrate, dark green microcrystalline solid. uv max (methanol): 350, 414, 473, 739 nm (log ε 4.33, 4.67, 5.06, 4.59).

Therapeutic Category

Antineoplastic adjunct (radiosensitizer).

Keywords

Antineoplastic Adjunct; Radiosensitizer