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1,3-Bis-[7-(3-amino-2,4,6-triiodophenyl)-heptanoyl]-2-oleoyl glycerol

DHOG

, MS, , PhD, and , PhD.

Author Information
, MS
Advanced Research Technologies (ART)
6330 Nancy Ridge Drive, San Diego, CA 92121, ac.tra@csarrubc
, PhD
Dow Chemical & Pharmaceutical Consulting
7001 Fairway Road, La Jolla, CA 92037, moc.oohay@gnitlusnocwodcw
, PhD
National Center for Biotechnology Information, National Library of Medicine, NIH, Bethesda, MD 20894, vog.hin.mln.ibcn@dacim

Created: ; Last Update: December 18, 2007.

Chemical name:1,3-Bis-[7-(3-amino-2,4,6-triiodophenyl)-heptanoyl]-2-oleoyl glycerolimage 46371141 in the ncbi pubchem database
Abbreviated name:DHOG
Synonym:Fenestra® LC, Fenestra® VC
Agent Category:Compound
Target:Nonspecific blood circulation and liver
Target Category:Nonspecific blood circulation and hepatic uptake pathway of chylomicron remnants
Method of detection:Computed tomography (CT)
Source of signal:Iodine
Activation:No
Studies:
  • Checkbox Rodents
  • Checkbox Non-primate non-rodent mammals
Click on the above structure for additional information in PubChem.

Background

[PubMed]

1,3-Bis-[7-(3-amino-2,4,6-triiodophenyl)-heptanoyl]-2-oleoyl glycerol (DHOG) is incorporated in an injectable lipid-in-water emulsion to be used as a contrast agent for the enhancement of x-ray computed tomography (CT) and micro-CT images of the bloodstream and liver in small animals (1-3). Micro-CT is widely used for imaging mice and rats and produces detailed images of bone material, but, with this technique, differentiation of soft tissue in the images is limited without the use of a contrast agent. Another limitation of micro-CT is the longer duration required to obtain a scan with most of the currently available instrumentation. Water-soluble contrast agents used for micro-CT are cleared from circulation during the time required to complete a scan (3). To overcome the limitations of water-based contrast agents used with the micro-CT instruments, DHOG was developed as a lipid-in-water emulsion (DHOG-LE) that mimics chylomicron remnants to enable its uptake by liver hepatocytes. The formulation designed for hepatobiliary imaging is referred to as DHOG-LC. A second formulation (DHOG-VC) contains a pegylated lipid in addition to the other lipid components of the DHOG-LC formulation. The increased retention time of DHOG-LE improved the visualization of abdominal organs by imaging at short intervals after injection. Use of the lipid-in-water emulsion contrast agent, particularly the DHOG-VC formulation, has also helped delineate the vascular structures in the animals.

The small particle size of the emulsion allows it to be taken up by hepatocytes in a receptor-mediated process (1). Apolipoprotein-E associates with the particle, and the complex binds to the hepatocyte receptor sites and enhances the liver image. Both the liver-selective and blood pool formulations of DHOG image the vascular system and the liver, but the time courses for visualization of the two systems differ (1, 2, 4). The selectivity and uptake by the liver is largely dependent on the physical parameters of the lipid emulsion. The timing of elimination from the liver appears to depend on the DHOG component because the various iodinated triglycerides have different clearance profiles (3). The pegylated lipid present in DHOG-VC is believed to physically block the apolipoprotein-E–binding hepatocyte receptor system, resulting in prolonged circulation in blood until the polyethylene glycol arms are cleaved from the molecule (2). Uptake by the liver is believed to occur by a mechanism similar to that seen with the liver-selective preparation after cleavage.

This chapter is a brief review of DHOG emulsions, which are iodinated contrast agents, for use only in small animals. The product is not approved for use in humans by the United States Food and Drug Administration or equivalent regulators in other countries.

Synthesis

[PubMed]

Weichert et al. and Counsell et al. have described the patented method for the synthesis of DHOG, the signal source (3, 5). DHOG was synthesized via dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP) coupling of 2-monoolein (1,2,3-trihydroxypropane 2-oleate) with two equivalents of the corresponding ω-(3-amino-2,4,6-triiodophenyl)alkanoic acid. The yield of the reported method was 79%. Radiolabeled preparations were prepared by radioiodinated (125I) isotope exchange in a melt of pivalic acid as described elsewhere (6). The labeled DHOG was purified on a silica gel column, and radiochemical purity was determined with thin-layer chromatography and high-performance liquid chromatography to be >96%. The specific activity of labeled DHOG was reported to range from 300 to 1,100 µCi/mg (3).

The lipid emulsion (DHOG-LC) was produced by combining DHOG, triolein, soy phosphatidyl choline, cholesterol, α-tocopherol, glycerol, and water (1). The blood pool formulation (DHOG-VC) contained the same components as DHOG-LC with an additional pegylated lipid, 1,2-diacyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (2). To produce the two formulations, the components were pre-blended in a Polytron mixer and subjected to high-pressure shear mixing with a microfluidizer. This produced a white, homogenous emulsion that was filter-sterilized and divided into vials, with or without subsequent heat sterilization.

In Vitro Studies: Testing in Cells and Tissues

[PubMed]

No publications are currently available.

Animal Studies

Rodents

[PubMed]

Using a liver-selective formulation in rats, Bakan et al. studied the effects of physicochemical properties on the biodistribution and imaging profiles of 125I-labeled DHOG in mice with a lipid emulsion containing 25 or 50 mg I/ml (1). The investigators observed that a 218 ± 5 nm volume-weighted mean particle diameter emulsion dosed at 25 mg I/kg body weight (bw) resulted in 66% of the radioactivity accumulating in the liver 30 min after administration. At half the dose (12.5 mg I/kg bw), 73% of the radioactivity accumulated in the liver at 30 min. With a higher dose (105 mg I/kg bw), however, only 28% of the radioactivity was observed in the liver at 30 min, with >40% still present in the blood. This suggested that the higher dose saturated the hepatic uptake mechanism. In this study, CT liver enhancement typically required 15–30 min to attain a peak contrast enhancement value and remained elevated for 2–3 h before declining to within 5% of pre-contrast values by 24 h. The spleen had the second highest amount of radioactivity with an accumulation of 15% of the injected dose at 30 min after the injection.

Doerr-Stevens et al. conducted a study in rats, using DHOG in hepatobiliary-selective lipid emulsions with different total lipid contents that were administered at doses between 50 and 300 mg I/kg bw (7). Similar levels of liver enhancement were observed with equivalent iodine doses independent of the initial lipid concentration. Except for the dose of 300 mg I/kg bw, all doses had a clearance time of ~24 h. With the dose of 300 mg I/kg bw, an elevated liver intensity was observed and it had a clearance kinetics of >24 h; contrast enhancement was still more than twice that of background but approximately half of the peak value at 24 h. This indicated that the mechanisms involved in clearance of the contrast agent from the liver were saturated beyond capacity. An enhanced image of the liver with an adequate definition of the organ anatomy was observed because the dose was increased. The enhancement improved as the iodine content increased up to the dose of 150 mg I/kg bw. However, the dose of 300 mg I/kg bw was reported to obscure tissue definition.

Using radiolabeled hepatobiliary and blood pool DHOG preparations to compare the pharmacokinetics of these formulations in Sprague-Dawley rats, Weichert et al. injected rats with a dose of 50 mg I/kg bw (2). Unlike the hepatobiliary DHOG-LC formulation that was cleared from blood circulation by 60 min, >56% of the DHOG-VC formulation remained in circulation during the first 60 min and ~40% of the radioactivity persisted in the blood after 3 h.

Ford et al. examined the time course of DHOG-VC in the blood pool of C57BL/6 mice with a dose of 500 mg I/kg bw (4). Five mice were imaged at various times between 0 and 24 h after the injection. A stable 1-h window for imaging vasculature was identified. By 24 h the contrast agent had cleared from blood circulation and peaked in the liver. The investigators concluded that this contrast agent could be used to study liver tumors and diseases.

Bakan et al. examined the contrast enhancement and elimination profile of DHOG-LC in normal and common bile duct–ligated rats (8). Imaging studies were performed after giving the animals a dose of 50mg I/kg bw. With this treatment the liver contrast enhancement increased steadily to a maximum at ~60 min and remained elevated for an additional 1–2 h. The intensity returned to pre-contrast levels by 24 h in the bile duct–ligated and control group animals (8). To study the elimination profile, control and surgically modified animals were given a bolus tail vein injection of 125I-labeled DHOG-LC at a dose of 25 mg I/kg bw. In control rats, radioactivity was predominantly eliminated via the hepatobiliary route, but in animals with ligated bile ducts the label was eliminated mainly through the urinary pathway during the same time (8).

Weichert et al. compared clinical CT scanning characteristics of DHOG-LC (45–100 mg I/kg bw) to iohexol (560 mg I/kg bw) in rats injected with Morris-7777 hepatoma cells either into the hepatic parenchyma or the portal vein (9). Pre-contrast scans were obtained 21 days after cell implantation, and images were obtained at 0–3 h and 24 h after administration of the contrast agent. Gross pathological measurements were performed to validate the imaging results. The investigators reported that DHOG-LC enhancement of the tumor image was similar to that with iohexol, but the enhancement persisted for up to 2 h after administration. From this study the investigators concluded that the liver uptake of DHOG-LC was rapid and enhanced lesion conspicuity at a significantly lower iodine dose level than the urographic contrast agents (9).

Subsequent investigators have looked at a variety of liver tumor models in different strains of mice (10-13). Weber et al. used direct injection of CT26 tumor cells into BALB/c mouse livers and imaged the livers with 500 mg I/kg DHOG-LC after 3–10 days of inoculation with the cells (10). Mean tumor sizes were comparable between contrast-enhanced CT values and histopathology measurements (2.2 and 2.3 mm). There were two false-negative readings and one false-positive reading on micro-CT. All erroneous readings occurred in mice with poor liver enhancement, and it was concluded that sufficient contrast agent was needed to accurately use this technique because the scans of good and fair quality resulted in accuracy, sensitivity, and specificity of 100%.

Micro-CT imaging studies were performed in nude mice bearing STC-1 tumors (n = 5 animals per group) 15 and 30 days after grafting. Animals were injected with 1,000 mg I/kg DHOG-LC and imaged at 2 and 4 h after the injection (11). The liver and spleen were clearly differentiated after administration of the contrast agent, reaching mean contrast-to-noise ratios of >2.0 for the liver and ~10 for the spleen at the different imaging times. In the spleen, quantification of the tumors with DHOG-LC was not precise, whereas in the liver tumors (0.3–1.5 mm) were detectable at day 30. Significant amounts of the contrast media were observed to persist in the animals for up to 15 days after a single injection, allowing quantitative follow-up of tumors both in the liver and the spleen without additional injection of contrast.

Desnoyers et al. performed an ex vivo micro-CT analysis of tumors in excised livers that had been injected with DHOG-LC before excision in fibroblast growth factor-19 transgenic mice (13). The investigators reported that excised tumor weights from the liver strongly correlated with the percent tumor volume (r2 = 0.993702) as determined by imaging.

Angiogenesis in fibrosarcoma tumors was imaged in rats with micro-CT and micro-digital subtraction angiography with a combination of DHOG-VC and Isovue, a conventional contrast agent (14). The DHOG-VC produced an enhancement of the vascular system, and Isovue provided functional information about the transit time and blood flow through the tumor. The investigators suggested that this approach could be used to understand angiogenesis and to evaluate anti-angiogenic therapies (14).

Lung tumor analysis is generally performed without the administration of a contrast agent. However, Li et al. observed that, although the administration of DHOG-VC was helpful in differentiating lung tumors from the heart and blood vessels, but it did not improve the visibility of lung tumors in a nude mouse metastatic lung disease model (15).

Using DHOG-VC, Kindlmann et al. examined the intermediate and large vessels of alveolar rhabdomyosarcomas in a transgenic mouse model (16). The investigators developed optimal scanning acquisition parameters and volume-rendering techniques to differentiate blood vessels from soft tissue and bone. The investigators suggested that CT with DHOG-VC represents the best potential for defining vessel diameter, tortuosity, and density for anti-angiogenesis models, but to visualize tumor capillaries it was necessary to develop instruments that had a higher resolution than those used in their study.

Imaging studies of the spleen have been performed with both the hepatobiliary-selective and blood pool DHOG formulations (11, 17-19). Investigators have published a series of papers describing techniques for three-dimensional segmentation of the spleen in micro-CT imaging using DHOG-VC with single-photon emission CT (SPECT)/CT and SPECT+ positron emission tomography (PET) modalities to quantify amyloid deposits in the spleen of a transgenic mouse model of amyloid A amyloidosis (17-19). The spleen contains interior follicles that do not contain blood, and the follicles were shown to be visualized after the administration of DHOG-LE (19).

Vascular leakage is one of the characteristic features of sepsis. Langheinrich and Ritman used the particle size of DHOG-VC to detect and evaluate the magnitude of endothelial defects of vascular permeability in rats caused by lipopolysaccharide-induced sepsis (20). From this study the investigators concluded that micro-CT in conjunction with a contrast agent could be used to characterize vascular permeability in lipopolysaccharide-induced sepsis models.

In a pilot study, Wisner et al. evaluated the use of DHOG-VC to study peripheral lymph dynamics by injecting 125I-labeled DHOG-VC interstitially into the footpad of a normal rat (21). Scintigraphic images of the animals showed that, although the majority of activity remained at the injection site, three small foci of activity were observed at the popliteal, inguinal, and paraaortic lymph nodes. From these results the investigators concluded that additional studies were necessary to confirm that DHOG-VC could be used for imaging the lymphatic system (21).

Rapid heart rate and small organ size make it difficult to image a mouse heart. DHOG-VC was evaluated for imaging of the mouse heart (22-26). Cardiac gating and ventilatory synchronization were used on C57BL/6 mice to compare Isovue-370 infusion (1 ml/h) and a bolus injection of DHOG-VC to image the mouse heart (22). With Isovue a maximum mean enhancement of ~500 HU in the aorta was obtained at 60 min, whereas with DHOG-VC a maximum of ~620 HU was observed in the aorta at 20 min, which dropped to ~500 HU during the 3 h when imaging was performed. Quantitative estimates were made for ejection fraction, stroke volume, and cardiac output on the basis of left ventricle volume measurements. The investigators concluded that DHOG-VC provided sufficient morphological and functional data for a standard method to determine the cardiac phenotype of the mice. In another study, a comparison was made between the images obtained with DHOG-VC for micro-CT and magnetic resonance microscopy (MRM) of myocardial infarction created by left coronary artery ligation in mice (23). The investigators reported visualization of significant changes (heart wall thinning and cardiac dynamics) with DHOG-VC that were similar to those observed with MRM. Drangova et al. were able to perform cardiac parameter measurements with DHOG-VC in a flat-panel type scanner with mice in a more typical, non-upright orientation (24).

Researchers have also pursued the development of micro-CT for phenotyping mice on the basis of morphological and functional imaging of the heart. Badea et al. imaged transgenic muscle LIM protein–null mice to acquire three-dimensional images with isotropic resolution in failing murine hearts and compared the micro-CT measurements with M-mode echocardiography (26). Mice that lack the muscle LIM protein develop dilated cardiomyopathy with myocardial hypertrophy and show signs of heart failure similar to those observed in humans with muscle LIM protein gene mutations and dilated cardiomyopathy. DHOG-VC was used for four-dimensional cardiac imaging and to determine the ejection fraction, systolic volume, cardiac output, and fractional shortening of the heart. From this study the investigators concluded that micro-CT with the use of a contrast agent significantly increased the precision and accuracy of detecting cardiomyopathy compared to either echocardiography or MRM (26).

Using DHOG-VC with CB-17 severe combined immunodeficiency/beige mice in a vascular graft placement study, Goyal et al. compared the results with CT and ultrasound imaging along with histologic evaluation (27). The study demonstrated that DHOG-VC could be used to confirm the patency and to investigate the anatomical details of tissue grafts. Lopez-Soler et al. used similar imaging techniques to compare different materials for small vascular grafting (28).

Micro-CT with DHOG-VC has also been used to study amyloidoma or atherosclerotic lesions in a mouse model (19, 29-31). Liang et al. demonstrated that a dual-modality micro-PET/micro-CT could be used with the administration of FDG and DHOG-VC for small animal imaging (32). The investigators showed that there was no interference between PET and CT data acquisition and that the use of DHOG-VC enhanced the soft tissue contrast. They also reported that the CT images were of sufficient quality for anatomical localization in the PET images (32).

Other Non-Primate Mammals

[PubMed]

Using DHOG-LC, Bakan et al. investigated the effect of cystic bile duct ligation and gallstone placement in dogs (8). Six dogs served as a control group with a sham operation, eight dogs underwent cystic duct ligation, and the gall bladder was removed from two dogs. A second surgery was performed on the animals from which the gall bladder was removed for a direct gallstone placement. Imaging was performed on animals 5–6 days after surgery before and up to 24 h after the administration of a dose of 25–50 mg I/kg bw of DHOG-LC (8). In normal dogs biliary enhancement was observed as early as 2–3 h after injection with a maximal enhancement at 6–8 h. The gall bladder was easily visualized in normal dogs. In animals with ligated cystic ducts, the gall bladder was not clearly visible because the contrast agent did not fill the gall bladder. In these animals, ductal dilatation resulted in prolonged enhancement of intrahepatic ducts and the liver. In animals with implanted gallstones, a filling defect in the gall bladder stump was observed along with ductal dilatation behind the obstruction (8). From this study the investigators concluded that DHOG-LC could be used to obtain information on the anatomy and pathology of the hepatobiliary system.

Liver tumor CT imaging was performed in a rabbit VX2 carcinoma model with DHOG-LC (9, 33). Lee et al. compared VX2 hepatic tumor imaging in rabbits with five different helical CT imaging techniques: unenhanced CT, CT performed with iohexol, CT arterial portography (CTAP) with iohexol, CT with DHOG-LC, and dual-contrast CT with a combination of iohexol and DHOG-LC (33). With DHOG-LC, peak enhancement occurred 25 min after administration and was sustained for ~2 h. A total of 64 VX2 tumors were examined in a blinded reading format. Liver to lesion attenuation differences were observed to be higher with DHOG-LC than with either iohexol-enhanced CT or CTAP (P < 0.05). Because the tumor images were not enhanced with DHOG-LC, there was an increased conspicuity of the organ relative to the other techniques. All methods effectively detected tumors that were ≥2.0 cm in size, but the small-diameter tumors were most accurately detected with the dual-contrast agent imaging followed (in descending order) by DHOG-LC, CTAP, and iohexol. The number of false-positives detected was higher with DHOG-LC–enhanced CT and the dual contrast–enhanced CT, but the number of true-positives detected also increased correspondingly (33). The investigators concluded that CT enhanced with DHOG-LC (particularly when combined with iohexol) provided greater sensitivity and liver-to-lesion attenuation differences with lower iodine doses than CT with iohexol alone or CTAP.

Using New Zealand White rabbits with VX2 carcinoma in the liver parenchyma, Weichert et al. investigated a combination of the hepatocyte-selective (DHOG-LC) and the blood pool (DHOG-VC) formulation for imaging and compared the results to those obtained with iohexol (34). The objective of the study was to increase the opacification of the hepatic vasculature to allow discrimination of lesions from vessels and reducing the false-positive tumor readings. Each rabbit underwent CT three times (non-enhanced CT, iohexol-enhanced CT, and DHOG-LC/DHOG-VC–enhanced CT) within 24 h. Half the animals received iohexol on the first day and half received the lipid emulsions; on day 2, the treatments were reversed (34). Iohexol scanning started 18 s after the injection. The DHOG-VC was injected 90 min before DHOG-LC, and the animals underwent CT 60 min after injection. Animals were euthanized after imaging, and the livers were fixed for 24 h and suspended in an agar solution to maintain true spatial orientation for sectioning. Lesions were identified visually and by palpation by two authors not involved in image reading, and slices of the liver were compared with CT scans for lesion number, size, and location (34). Data obtained from the study indicated that the use of a dual-lipid emulsion was superior to the use of iohexol alone for imaging because it showed a higher sensitivity and specificity with the blinded readings. Both techniques provided comparable liver opacification, but the dual-lipid emulsion scans provided less lesion enhancement, which improved liver-to-lesion contrast. The investigators also observed that a dose of the dual DHOG contrast agents <300 mg I/kg bw was not optimal to perform this type of work (34). They concluded that, compared to iohexol-enhanced CT, the dual DHOG emulsion quantitatively enhanced the CT and qualitatively improved lesion detection in the liver.

Non-Human Primates

[PubMed]

No publications are currently available.

Human Studies

[PubMed]

No publications are currently available.

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    This MICAD chapter is not included in the Open Access Subset, because it was authored / co-authored by one or more investigators who was not a member of the MICAD staff.

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