Synthesis of bombesin analogues for radiolabeling with rhenium‐188

Safavy, Ahmad; Khazaeli, M. B.; Qin, Haoyu; Buchsbaum, Donald J.

doi:10.1002/(sici)1097-0142(19971215)80:12+<2354::aid-cncr4>3.3.co;2-j

Cited by 9 publications

(4 citation statements)

References 10 publications

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“…5, 6 Analogues of BN with modified structures exhibit a similar or even higher affinity for these receptors. 7,8 The pharmacological effect of BN has also been found to extend into various physiological aspects such as hypertensive action, contractive effect on uterus, colon, or ileum, locomotor activity, stimulating action on the gastric secretion, hyperglycemic effect, and increasing insulin secretion. [9][10][11] It has been also proven that BN inhibits food intake in mammalian species.…”

Section: Introductionmentioning

confidence: 99%

Surface‐enhanced Raman difference between bombesin and its modified analogues on the colloidal and electrochemically roughen silver surfaces

Podstawka¹,

Ozaki²

2008

Biopolymers

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In this article, surface-enhanced Raman scattering (SERS) spectra of bombesin (BN) and its six modified analogues ([D-Phe(12)]BN, [Tyr(4)]BN, [Tyr(4),D-Phe(12)]BN, [D-Phe(12),Leu(14)]BN, [Leu(13)-(R)-Leu(14)]BN, and [Lys(3)]BN) on a colloidal silver surface are reported and compared with SERS spectra of these species immobilized onto an ellectrochemically roughen silver electrode. Changes in enhancement and wavenumber of proper bands upon adsorption on different silver surfaces are consistent with BN and its analogues adsorption primarily through Trp(8). Slightly different adsorption states of these molecules are observed depending upon natural amino acids substitution. For example, the indole ring in all the peptides interacts with silver nanoparticles in a edge-on orientation. It is additionally coordinated to the silver through the N(1)--H bond for all the peptides, except [Phe(12)]BN. This is in contrary to the results obtained for the silver roughen electrode that show direct but not strong N(1)--H/Ag interaction for all peptides except [D-Phe(12),Leu(14)]BN and [Leu(13)-(R)-Leu(14)]BN. For BN only C==O is not involved in the chemical coordination with the colloidal surface. [Lys(3)]BN and BN also adsorb with the C--N bond of NH(2) group normal and horizontal, respectively, to the colloidal surface, whereas C--NH(2) in other peptides is tilted to this surface. Also, the Trp(8) --CH(2)-- moiety of only [Tyr(4)]BN, [Lys(3)]BN, and [Tyr(4),D-Phe(12)]BN coordinates to Ag, whereas the Phe(12) ring of [Phe(12)]BN, [Tyr(4),D-Phe(12)]BN, and [D-Phe(12),Leu(14)]BN assists in the peptides binding only on the colloidal silver.

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Section: Introductionmentioning

confidence: 99%

Surface‐enhanced Raman difference between bombesin and its modified analogues on the colloidal and electrochemically roughen silver surfaces

Podstawka¹,

Ozaki²

2008

Biopolymers

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“…Peptide analogues that recognize BN receptors on malignant tissue can be also used as carriers for radionuclides or cytotoxic moieties. Numerous radionuclide derivatives of BN have been proposed for imaging and targeted radiotherapy of BN receptor-positive tumors (Safavy et al, 1997;Baidoo et al, 1998;Breeman et al, 1999). In our laboratory, we developed cytotoxic hybrids of BN-like peptides containing doxorubicin or 2-pyrrolinodoxorubicin, which retain high affinity to BN receptors and potent anti-tumor activity (Nagy et al, 1997;Kiaris et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

in vivo inhibition of PC-3 human androgen-independent prostate cancer by a targeted cytotoxic bombesin analogue, AN-215

Płonowski¹,

Nagy²,

Schally³

et al. 2000

Int. J. Cancer

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The effectiveness of chemotherapy targeted to bombesin (BN) receptors was evaluated in nude mice bearing PC‐3 human androgen‐independent prostate cancers. Cytotoxic BN analogue AN‐215, consisting of 2‐pyrrolinodoxorubicin (AN‐201) linked to BN‐like carrier peptide RC‐3094, was injected i.v. at 150 nmol/kg on days 1, 11 and 21. After treatment with AN‐215, tumor volume was 69% (p < 0.01) smaller than that in controls and tumor doubling time was extended from 8.5 ± 0.7 days to 20.3 ± 3.5 days (p < 0.05). Cytotoxic radical AN‐201, carrier RC‐3094 and their unconjugated mixture administered at the same dosage were ineffective. The mortality rate was 12.5% in the AN‐201 group and 16.7% in the group treated with the mixture, but no deaths occurred in mice receiving AN‐215. Because the ester bond linking AN‐201 to the carrier molecule is hydrolyzed much faster in mouse serum than in human serum, in the second experiment we investigated the tolerance to AN‐215 and its effect in nude mice bearing PC‐3 tumors after pharmacological inhibition of serum carboxylesterases. Two applications of AN‐201 at 200 nmol/kg were lethal, whereas no mortality was observed after 4 injections of AN‐215 at the same dose. Administration of 200 nmol/kg AN‐215 on days 1, 7, 17 and 26 again produced 69% tumor inhibition. BN receptors on membranes of PC‐3 tumors were detected by 125I‐[Tyr4]BN binding, and expression of mRNA for BRS‐3 and GRP‐R subtypes was also found. AN‐215 showed a high affinity to PC‐3 tumors, displacing the radioligand at an IC50 of 12.95 ± 0.35 nM. Because BN receptors are present on primary and metastatic prostate cancer, targeted chemotherapy with AN‐215 might benefit patients with advanced prostatic carcinoma who relapsed androgen ablation. Int. J. Cancer 88:652–657, 2000. © 2000 Wiley‐Liss, Inc.

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“…The 188 Re was first reduced with stannous ion in the presence of citric acid at 95 °C for 1 h before transchelating at pH 7 to the trisuccin linked to the antibody. The transchelation was achieved at 40 °C with a labeling efficiency of about 90 % within 45 min [87]. Transchelation using 2-hydroxy-2-methyl propionic acid in place of citric acid was also found to work well [88].…”

Section: Trisuccinmentioning

confidence: 92%

“…The transchelation was achieved at 40 °C with a labeling efficiency of about 90 % within 45 min [87]. Transchelation using 2-hydroxy-2-methyl propionic acid in place of citric acid was also found to work well [88]. The structure of both the technetium and rhenium complexes is unknown.…”

Section: Trisuccinmentioning

confidence: 99%

Labeling Biomolecules with Radiorhenium - A Review of the Bifunctional Chelators

Liu

Hnatowich

2007

ACAMC

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For radiotherapy, biomolecules such as intact antibodies, antibody fragments, peptides, DNAs and other oligomers have all been labeled with radiorhenium ((186)Re and (188)Re). Three different approaches have been employed that may be referred to as direct, indirect and integral labeling. Direct labeling applies to proteins and involves the initial reduction of endogenous disulfide bridges to provide chelation sites. Indirect labeling can apply to most biomolecules and involves the initial attachment of an exogenous chelator. Finally, integral labeling is a special case applying only to small molecules in which the metallic radionuclide serves to link two parts of a biomolecule together in forming the labeled complex. While the number of varieties for the direct and integral radiolabeling approaches is rather limited, a fairly large and diverse number of chelators have been reported in the case of indirect labeling. Our objective herein is to provide an overview of the various chelators that have been used in the indirect labeling of biomolecules with radiorhenium, including details on the labeling procedures, the stability of the radiolabel and, where possible, the influence of the label on biological properties.

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Synthesis of bombesin analogues for radiolabeling with rhenium‐188

Cited by 9 publications

References 10 publications

Surface‐enhanced Raman difference between bombesin and its modified analogues on the colloidal and electrochemically roughen silver surfaces

Surface‐enhanced Raman difference between bombesin and its modified analogues on the colloidal and electrochemically roughen silver surfaces

in vivo inhibition of PC-3 human androgen-independent prostate cancer by a targeted cytotoxic bombesin analogue, AN-215

Labeling Biomolecules with Radiorhenium - A Review of the Bifunctional Chelators

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