A novel 99mTc-labeled testosterone derivative as a potential agent for targeting androgen receptors

Das, Tapas; Banerjee, Sharmila; Samuel, Grace; Bapat, Ketaki; Subramanian, Suresh; Pillai, M.R.A.; Venkatesh, Meera

doi:10.1016/j.bmcl.2006.08.081

Cited by 9 publications

(12 citation statements)

References 14 publications

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“…Plain liposomes may display lower toxicity and sustained release characters but may have limited application as they may not provide desired concentration as the tumor sites. Testosterone is the endogenous ligand investigated for the imaging (Das et al, 2006), targeted drug delivery (Betsch, 1990;Roth et al, 1995;Kuduk et al, 2000), or immunological study (Rajkowski et al, 1997), via various testosterone ligand conjugates, so far as androgen receptors are present at most of the prostate tumor surface/membrane, e.g. DU-145 and LNCaP, cells.…”

Section: Resultsmentioning

confidence: 99%

“…The testosterone was coupled with DSPE in two steps using the methods reported by Das et al (2006) and Hwang et al (1992), with slight modifications. Briefly, 25 mg (0.087 mmol) of testosterone and 45 mg (0.413 mmol) carboxy methoxylamine hemihydrochloride were dissolved in 2.1 ml mixture of pyridine/methanol/water (1:4:1 v/v).…”

Section: Synthesis Of Testosterone Lipid Conjugate (T-dspe)mentioning

confidence: 99%

“…Testosterone, a primary male sex hormone ligand, regulates the sexual and other regulatory function in male. Various conjugates of testosterone have been evaluated for immunological assay, ARs imaging/targeting purposes as these receptors are over-expressed at the tumor surface (Katzenellenbogen et al, 1995;Kuduk et al, 2000;Hoffmann & Sommer, 2005;Das et al, 2006). Thus, the androgen receptor-specific testosterone lipid conjugate (T-DSPE) present at the liposomes membrane may direct the drug delivery to the ARs target organs and ARs over-expressed tumors.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, liposomes have also been implicated for the site-specific gene/drug delivery using estrogen as a targeting ligand (Reddy & Banerjee, 2005;Rai et a., 2008). ARs are the members of nucleic receptor family which are over-expressed at the tumor surface in various cancer cells like DU-145 (Das et al, 2006), and LNCaP cells (Kampa et al, 2002;Kidwai et al, 2004). Testosterone, a primary male sex hormone ligand, regulates the sexual and other regulatory function in male.…”

Section: Introductionmentioning

confidence: 99%

“…Various receptors which are over-expressed at tumor cells are epidermal growth factor receptor (EGFR) (Torp et al, 1991;Rusch et al, 1996), folate receptor (FRs) (Weitman et al, 1992), transferrin receptor (TRs) (Recht et al, 1990), fucose receptor Seymour, 1994), estrogen receptors (ERs) (Harding et al, 1990;Loven et al, 1990), and androgen receptor (ARs) (Kampa et al, 2002;Das et al, 2006), etc. These ligands have been proposed for site-specific delivery of different imaging agents or therapeutic agents via conjugated drug delivery.…”

Section: Introductionmentioning

confidence: 99%

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Testosterone Lipid Conjugate (T-dspe)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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For the purpose of this review, active targeting in cancer research encompasses strategies wherein a ligand for a cell surface receptor expressed on tumor cells is used to deliver a cytotoxic or imaging cargo. This area of research is more than two decades old, but in those 20 and more years, how many receptors have been studied extensively? What kinds of the ligands are used for active targeting? Are they mostly naturally occurring molecules such as folic acid, or synthetic substances developed in campaigns for medicinal chemistry efforts? This review outlines the most important receptor or ligand combinations that have been used in active targeting to answer these questions, and therefore to address the most important one of all: is research in active targeting affording diminishing returns, or is this an area for which the potential far exceeds progress made so far?

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Synthesis and Characterization of Nonsteroidal-Linked M(CO)₃⁺(M = ^99mTc, Re) Compounds Based on the Androgen Receptor Targeting Molecule Flutamide

Morely

Silva-Lopez

et al. 2008

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Androgen receptors are overexpressed in most primary and metastatic prostate cancers. A series of single photon emission computed tomography imaging agents (SPECT) utilizing the organometallic radioactive imaging species, fac-99mTc(OH(2))(3)(CO)(3)+, were prepared on the basis of the structure of Flutamide, a potent nonsteroidal antiandrogen prostate cancer drug. Novel bifunctional chelate-linked Flutamide analogues were prepared using a newly developed universal alkylating reagent, 2-bromo-N-[4-nitro-3-(trifluoromethyl)phenyl]-acetamide, 1. From compound 1, several ligands (i.e., cysteine 2, histidine 5, imidazole 3) were conjugated to the flutamide derivative to yield targeting ligands capable of either tridentate or monodentate coordination in a "2 + 1" complex. fac-Re(CO)(3)+ complexes were prepared and characterized with the functionalized conjugates to yield fac-Re(CO)(3)(2-amino-3-(1-(2-(4-nitro-3-(trifluoromethyl)phenylamino)-2-oxoethyl)-1H-imidazol-4-yl) propanoate), 4, fac-Re (CO)(3)(2-(S-cysteinyl)-N-[4-nitro-3-(trifluoromethyl) phenyl]-acetamide), 6, and fac-Re(CO)(3)(picolinate)(2-(1H-imidazol-1-yl)-N-[4-nitro-3-(trifluoromethyl)phenyl]-acetamide), 7. The corresponding radioactive 99mTc analogues were prepared and stability studies of the radioactive compounds were also conducted.

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A novel 99mTc-labeled testosterone derivative as a potential agent for targeting androgen receptors

Cited by 9 publications

References 14 publications

Targeted delivery of an anti-cancer agent via steroid coupled liposomes

Targeted delivery of an anti-cancer agent via steroid coupled liposomes

Small Molecules for Active Targeting in Cancer

Synthesis and Characterization of Nonsteroidal-Linked M(CO)₃⁺(M = ^99mTc, Re) Compounds Based on the Androgen Receptor Targeting Molecule Flutamide

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A novel 99mTc-labeled testosterone derivative as a potential agent for targeting androgen receptors

Cited by 9 publications

References 14 publications

Targeted delivery of an anti-cancer agent via steroid coupled liposomes

Targeted delivery of an anti-cancer agent via steroid coupled liposomes

Small Molecules for Active Targeting in Cancer

Synthesis and Characterization of Nonsteroidal-Linked M(CO)3+(M = 99mTc, Re) Compounds Based on the Androgen Receptor Targeting Molecule Flutamide

Contact Info

Product

Resources

About

Synthesis and Characterization of Nonsteroidal-Linked M(CO)₃⁺(M = ^99mTc, Re) Compounds Based on the Androgen Receptor Targeting Molecule Flutamide