Labelling of octreotide using <sup>76</sup>Br‐prosthetic groups

Yngve, Ulrika; Khan, Tanweera Shaheena; Bergström, Mats; Långström, Bengt

doi:10.1002/jlcr.478

Cited by 10 publications

(4 citation statements)

References 21 publications

(13 reference statements)

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“…The use of positron-emitting halogen radionuclides, specifically 124 I (t 1/2 ) 4.2 d) and 76 Br (t 1/2 ) 16 h), to label radiopharmaceuticals for PET imaging has increased greatly over the past decade. For example, 76 Br has been labeled to octreotide (5) and 76 Br-labeled bromodeoxyuridine has been investigated as a tumor and brain imaging agent (6,7). Iodine-124 is currently used to produce [ 124 I]-5-iodo-2′-fluoro-1-β-D-arabinofuranosyl-uracil (FIAU) which has been used to image gene expression (8).…”

Section: Introductionmentioning

confidence: 99%

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

Lewis

Kim

et al. 2002

Bioconjugate Chem.

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The goal of this study was to evaluate a somatostatin receptor ligand, DOTA-D-Tyr(1)-octreotate (DOTA-DY1-TATE), that has the chelator 1,4,7,10-tetraazacyclotetradecane-N,N',N'',N'"-tetraacetic acid (DOTA) attached to the D-Tyr(1) residue, allowing radiolabeling with both radiohalogens and radiometals. A potential advantage of having a chelator attached to the Tyr(1) residue is that halogen radiolabels may residualize or remain trapped in tumor cells rather than clear from the tumor. DOTA-DY1-TATE was synthesized by solid-phase methods and radiolabeled with (61)Cu, (64)Cu, and (125)I in high radiochemical purity and specific activity. A competitive binding assay demonstrated that (nat)Cu-DOTA-DY1-TATE and DOTA-(nat)I-DY1-TATE had comparable affinity to (nat)In-DTPA-OC in AR42J rat pancreatic tumor cells membranes. (61)Cu-DOTA-DY1-TATE had a dissociation constant (K(d)) of 176.4 pM and a receptor concentration (B(max)) of 244.4 fmol/mg. A tumor uptake of 1.515 %ID/g was determined for (64)Cu-DOTA-DY1-TATE and 0.814 %ID/g for DOTA-(125)I-DY1-TATE in AR42J tumor bearing Lewis rats at 1 h postinjection. DOTA-(125)I-DY1-TATE remained in the tumor at a higher concentration out to 4 h postinjection, suggesting that the iodine may have residualized in the tumor cells. MicroPET imaging of (64)Cu-DOTA-DY1-TATE in AR42J tumor bearing rats and SCID mice at 2 h postinjection showed significant uptake and good contrast in the thigh tumors in the rat model and in the neck and thigh tumors of the mouse. This study demonstrates that DOTA-DY1-TATE is a somatostatin analogue that can be labeled with both metal and halogen radionuclides, and its (64)Cu- and (125)I-radiolabeled compounds showed somatostatin receptor-mediated uptake in normal and tumor tissues.

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Section: Introductionmentioning

confidence: 99%

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

Lewis

Kim

et al. 2002

Bioconjugate Chem.

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“…The only significant contribution to the total activity 16 hours post EOB is due to 76 Br. There is < 1% 75 Br and 77 Br Numerous preparations of lower specific activity radiobrominated pharmaceuticals are reported in the literature [16][17][18][19][20]. The low SA is due to carrier bromide present in the target material, reagents, or solvents.…”

Section: Resultsmentioning

confidence: 99%

Semi-remote production of Br-76 and preparation of high specific activity radiobrominated pharmaceuticals for PET studies

Szajek¹,

Kao²,

Kiesewetter³

et al. 2004

Radiochimica Acta

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The PET radionuclide 76 Br (t 1/2 = 16.2 h) can be easily produced utilizing the nuclear reaction As( 3 He, 2n) 76 Br. We use high-purity arsenic targets and isolate radioactive bromide by chromic acid oxidation followed by simple distillation of [ 76 Br] hydrogen bromide using a semi-remote apparatus. Use of reagents with little or no carrier bromine yields high specific activity radiobrominated pharmaceuticals prepared from the distilled [ 76 Br] hydrogen bromide.

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“…Реактивы и растворители получены от компании «Enamin». Метил арилкарбоксиимидаты (5а-е) получены по стандарт-ным методикам и использовались без очистки [13]. Общая методика получения 5-(3-аминофенил)-2,4-дигидро-3H-1,2,4-триазол-3-онов (8a, b).…”

Section: экспериментальная частьunclassified

Synthesis of functionally substituted of 5-aryl-1,2,4-triazol-3-ones.

Толкунов¹,

Smirnova²,

Tolkunov³

et al. 2017

Chemical

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Разработан метод получения разнозамещенных 5-арил-1,2,4-триазол-3-онов, термической цикли-зацией амидразонов, получаемых in situ из метил бензимидатов и метилкарбазата. Предложена оп-тимальная методика восстановления нитрофенилтриазолонов сульфидом натрия в диоксане. Соот-ветствующие аминоарилтриазолоны получены с выходами 74-76 %.Карбоксипроизводные фенилтриазолонов синтезировали карбонилированием бромфенилтриазо-лонов окисью углерода в присутствии [1,1'-бис(дифенилфосфино)ферроцен]дихлорпалладия (II) (Pd(dppf)Cl 2 ) и триэтиламина в метаноле. Показано что, окисление толилтриазолона перманганатом калия в щелочной среде сопровождается деструкцией триазолонового цикла и приводит к терефта-левой кислоте. Полученные аминофенил-и карбоксифенил-1,2,4-триазол-3-оны представляют инте-рес в плане изучения биологической активности, а также для дальнейшей химической модификации.Ключевые слова: циклизация, карбонилирование, 5-арил-1,2,4-триазол-3-оны, метил карбазат, метил арилкарбоксиимидаты, [1,1'-бис(дифенилфосфино)ферроцен]дихлорпалладий (II). Цель настоящего исследования -разработка методов синтеза 5-арил-1,2,4-триазол-3-онов, содержащих в арильном кольце амино-и карбоксигруппы, легко поддающиеся дальнейшей химической модификации.В настоящее время для получения 5-арил-1,2,4-триазол-3-онов предложено несколько общих синтетических подходов. Это окислительная циклизация семикарбазидов арилальдегидов (1) [6,7], а также щелочная циклизация ацилсемикарбазидов (2) (схема 1) [8,9]. Схема 1Первый метод неудобен тем, что исходные семикарбазоны (1) трудно растворимы практиче-ски во всех органических растворителях и поэтому наработка значительных количеств триазо-лонов (3) труднодостижимая задача. Щелочная циклизация ацилсемикарбазидов (2) зависит от заместителей в бензольном кольце и проходит, как правило, с выходами 10-30 % [8], редко до 50 % [9]. Побочный процесс в этом методе -гидролиз семикарбазидов (2) до соответствующих бензойных кислот. Обсуждение результатовДля синтеза целевых арилтриазолонов (7a-e) использовалась термическая циклизация амид-разонов (6), получаемых in situ из метил бензимидатов (5) и метилкарбазата (схема 2). Перво-* Институт физико-органической химии и углехимии им. Л.М. Литвиненко НАН Украины

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Labelling of octreotide using ⁷⁶Br‐prosthetic groups

Abstract: SummaryA method for labelling the octapeptide octreotide (d^Phe-Cys-Phe-d-TrpLys-Thr-Cys-Thr(ol)) with the positron emitting 76 Br (T 1=2 =16 h) ispresented.

Cited by 10 publications

References 21 publications

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

Semi-remote production of Br-76 and preparation of high specific activity radiobrominated pharmaceuticals for PET studies

Synthesis of functionally substituted of 5-aryl-1,2,4-triazol-3-ones.

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Labelling of octreotide using 76Br‐prosthetic groups

Abstract: SummaryA method for labelling the octapeptide octreotide (d^Phe-Cys-Phe-d-TrpLys-Thr-Cys-Thr(ol)) with the positron emitting 76 Br (T 1=2 =16 h) ispresented.

Cited by 10 publications

References 21 publications

DOTA−d-Tyr1-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

DOTA−d-Tyr1-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

Semi-remote production of Br-76 and preparation of high specific activity radiobrominated pharmaceuticals for PET studies

Synthesis of functionally substituted of 5-aryl-1,2,4-triazol-3-ones.

Contact Info

Product

Resources

About

Labelling of octreotide using ⁷⁶Br‐prosthetic groups

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy

DOTA−d-Tyr¹-Octreotate: A Somatostatin Analogue for Labeling with Metal and Halogen Radionuclides for Cancer Imaging and Therapy