Iodinated hydroxyphenyl and hydroxynaphthyl porphyrins as tumour localisers

Zanelli, G. D.; Kaelin, Alfred C.

doi:10.1038/bjc.1990.155

Cited by 5 publications

(1 citation statement)

References 6 publications

(9 reference statements)

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“…2b). Similar to our observations, it has been reported that an insoluble iodinated hydroxynaphthyl porphyrin was accumulated in higher concentrations in the spleen as compared to the liver, using a vehicle composed of dimethyl sulfoxide, ethanol and water (34).…”

Section: Levels Of Isobosinc In Spleen and Liversupporting

confidence: 92%

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Zuk

Rihter

Kenney

et al. 1996

Photochem & Photobiology

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Bis(di-isobutyl octadecylsiloxy)silicon 2,3-naphthalocyanine (isoBOSINC) is a representative of a group of naphthalocyanine derivatives with spectral and photophysical properties that make them attractive candidates for photodynamic therapy (PDT). Tissue distributions were studied in tumor-bearing rats as a function of delivery system and time following administration. The tumor model was an N-(4-[5-nitro-2-furyl]-2-thiazolyl) formamide (FANFT)-induced urothelial cell carcinoma transplanted into one hind leg of male Fischer 344 rats; isoBOSINC was delivered to the rats by intravenous injection of 0.50 mg/kg of body weight as a suspension either in 10% Tween 80 in saline (Tween) or 10% (Cremophor EL + propylene glycol) in saline (Cremophor). The isoBOSINC was isolated from several tissues and organs, as well as tumors and peritumoral muscles and skin. Quantitation was by a high-performance liquid chromatographic technique with detection that utilizes the native fluorescence of the naphthalocyanine derivative. Independent of the delivery system, the dye was retained in tumors at higher concentrations than in normal tissues, except for spleen and liver. The isoBOSINC retention in tumors was high and was vehicle dependent. For Tween, the maximal ratio of dye in tumor versus peritumoral muscle occurred 12 h after injection; for Cremophor, the maximal ratio occurred later, 336 h postinjection. When the drug was delivered in Tween, isoBOSINC in serum showed two compartment kinetics: half-lives of about 2 and 11 h were found for the distribution and the elimination phases, respectively. When Cremophor was the vehicle, the elimination half-life was about 20 h, and one compartment kinetics was observed. The latter findings may explain the generally higher levels of the dye attained by the tissues at later times with Cremophor as the vehicle. An interesting exception was that after 7 and 14 days postinjection in Tween, the levels of dye found in testes were six- to seven-fold higher than those found after Cremophor delivery. Levels of dye were very low or not detectable in the brain. Optimal parameters for PDT of tumors with this novel photosensitizer are clearly time- and vehicle-dependent, and future PDT studies will need to incorporate these modulators.

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Section: Levels Of Isobosinc In Spleen and Liversupporting

confidence: 92%

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Zuk

Rihter

Kenney

et al. 1996

Photochem & Photobiology

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Soluble precipitable porphyrins for use in targeted molecular brachytherapy

2008

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In a new therapy that aims to concentrate and immobilize therapeutic radionuclides in nanoscale assemblies within solid tumors, a soluble precipitable reagent (SPR) is administered as the radionuclide carrier and is converted to non-diffusible precipitate by an enzyme located in tumor tissues. To meet the objective of such an SPR, we have prepared and examined a class of porphyrin-alkyldiphosphates that are soluble in aqueous solution and that are rendered insoluble upon removal of the two phosphate groups. The porphyrins examined herein are of the trans-AB architecture wherein the substituents are a bis(dihydroxyphosphoryloxy)alkyl group and a phenyl (or p-bromophenyl) group. Provisions for later incorporation of radionuclides have been established by preparation of the analogous copper chelate or the meso-iodo free-base porphyrin. Altogether, four porphyrins bearing a bis(dihydroxyphosphoryloxy)alkyl group were examined and found to exhibit satisfactory solubility in water (41 mM). Dephosphorylation reactions have been carried out in vitro using the enzyme shrimp alkaline phosphatase. In each case, enzymeinduced precipitation was observed. The soluble-to-insoluble conversion has been examined by visual inspection, absorption spectroscopy, electrospray ionization mass spectrometry, and nephelometry using non-radiolabeled porphyrins.

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Tissue Distribution of BacteriochlorinaLabelled with^99mTc-pertechnetate in Hamster Greene Melanoma

Schuitmaker¹,

Feitsma

Korver

et al. 1993

International Journal of Radiation Biology

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Bacteriochlorin a (BCA), a new photosensitizer for photodynamic therapy, was labelled with 99mTc-pertechnetate following a method for the irreversible coupling of 99mTc-pertechnetate to proteins. Biodistribution studies were conducted in male Syrian Golden hamsters with hamster Greene melanoma implanted s.c. on both sides of the abdomen. After i.v. administration of 99mTc-pertechnetate-labelled BCA 17 tissue and fluid samples were analysed at time intervals ranging from 1 to 24 h. Technetium-labelled BCA showed a pronounced affinity for tissues belonging to the reticuloendothelial system. Peak activities, 1 h post-injection, were distributed as follows: lung, liver, spleen, urine > small intestine, kidney, blood, heart, stomach, large intestine > thyroid, tumour, bone, skin, muscle, eye >> brain. It is concluded that the technetium-labelled photosensitizer BCA does not accumulate selectively in neoplastic tissue.

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Iodinated hydroxyphenyl and hydroxynaphthyl porphyrins as tumour localisers

Cited by 5 publications

References 6 publications

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Soluble precipitable porphyrins for use in targeted molecular brachytherapy

Tissue Distribution of BacteriochlorinaLabelled with^99mTc-pertechnetate in Hamster Greene Melanoma

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Iodinated hydroxyphenyl and hydroxynaphthyl porphyrins as tumour localisers

Cited by 5 publications

References 6 publications

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Effect of Delivery System on the Pharmacokinetics and Tissue Distribution of bis(Di‐lsobutyl Octadecylsiloxy)Silicon 2,3‐Naphthalocyanine (isoBOSINC), a Photosensitizer for Tumor Therapy

Soluble precipitable porphyrins for use in targeted molecular brachytherapy

Tissue Distribution of BacteriochlorinaLabelled with99mTc-pertechnetate in Hamster Greene Melanoma

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Tissue Distribution of BacteriochlorinaLabelled with^99mTc-pertechnetate in Hamster Greene Melanoma