Depreotide
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Depreotide

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Depreotide is an oligopeptide.

Category
Others
Catalog number
BAT-010032
CAS number
161982-62-3
Molecular Formula
C65H96N16O12S2
Molecular Weight
1357.68
Depreotide
IUPAC Name
(2S)-6-amino-2-[[(2R)-2-[[(2S)-6-amino-2-[[(2S)-2-amino-3-[[2-[2-[(2S,5S,8S,11R,14S,17S)-14-(4-aminobutyl)-5-benzyl-8-[(4-hydroxyphenyl)methyl]-11-(1H-indol-3-ylmethyl)-4-methyl-3,6,9,12,15,18-hexaoxo-17-propan-2-yl-1,4,7,10,13,16-hexazacyclooctadec-2-yl]ethylsulfanyl]acetyl]amino]propanoyl]amino]hexanoyl]amino]-3-sulfanylpropanoyl]amino]hexanamide
Synonyms
NeoTec; P 829; P829; D03687; P-829
Purity
95%
Density
1.24g/cm3
Boiling Point
1654.2±65.0°C at 760 mmHg
InChI
InChI=1S/C65H96N16O12S2/c1-38(2)55-64(92)76-49(26-30-95-37-54(83)72-35-44(69)57(85)74-47(20-10-13-28-67)58(86)79-52(36-94)62(90)73-46(56(70)84)19-9-12-27-66)65(93)81(3)53(32-39-15-5-4-6-16-39)63(91)78-50(31-40-22-24-42(82)25-23-40)60(88)77-51(33-41-34-71-45-18-8-7-17-43(41)45)61(89)75-48(59(87)80-55)21-11-14-29-68/h4-8,15-18,22-25,34,38,44,46-53,55,71,82,94H,9-14,19-21,26-33,35-37,66-69H2,1-3H3,(H2,70,84)(H,72,83)(H,73,90)(H,74,85)(H,75,89)(H,76,92)(H,77,88)(H,78,91)(H,79,86)(H,80,87)/t44-,46-,47-,48-,49-,50-,51+,52-,53-,55-/m0/s1
InChI Key
XXXSJQLZVNKRKX-YQRDHHIGSA-N
Canonical SMILES
CC(C)C1C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)CC5=CC=CC=C5)C)CCSCC(=O)NCC(C(=O)NC(CCCCN)C(=O)NC(CS)C(=O)NC(CCCCN)C(=O)N)N
1. 99mTc-depreotide in the evaluation of bone infection and inflammation
Nikolaos D Papathanasiou, Phivi E Rondogianni, Nikoletta K Pianou, Pinelopi A Karampina, Evangelia A Vlontzou, Ioannis E Datseris Nucl Med Commun. 2008 Mar;29(3):239-46. doi: 10.1097/MNM.0b013e3282f20e30.
Background and aim: (99m)Tc-depreotide is a (99m)Tc-labelled somatostatin analogue, with high affinity for the 2, 3 and 5 subtypes of somatostatin receptors. These particular receptors are over-expressed on the surface of activated leucocytes, which mediate inflammatory response. Based on this property this study tried to investigate whether (99m)Tc-depreotide scintigraphy could be a useful complementary method in the investigation of bone infection and inflammation. Methods: Twenty-three patients, who were investigated for probable osteomyelitis, underwent three-phase bone scintigraphy followed by (99m)Tc-depreotide scintigraphy. Clinical and laboratory findings, complementary imaging procedures, clinical follow-up and bone biopsy established the final diagnosis. (99m)Tc-depreotide scintigraphy was performed 3 h after the intravenous administration of 555-740 MBq of the radiopharmaceutical. Scintigraphic images were, at first, blindly interpreted alone and then in comparative assessment with bone scans. Results: (99m)Tc-depreotide was positive in 12/12 cases of active osteomyelitis, one case of recent femoral head osteonecrosis and 6/9 rheumatoid arthritis sites. Negative (99m)Tc-depreotide scans were acquired in five cases of 'no-inflammation' (an uncomplicated fracture, an aseptic loosening of prosthesis, an old osteonecrosis, a healed and a successfully treated osteomyelitis), as well as in 14/14 total sites of degenerative arthritis-osteoarthropathy. In five cases (septic arthritis, periodontal and soft tissue infections) (99m)Tc-depreotide was positive, though spatially discordant with bone scintigraphy, delineating precisely the focus of infection. Conclusion: (99m)Tc-depreotide can be a useful complementary imaging method in the evaluation of bone infection and inflammation. Its combination with three-phase bone scintigraphy seems to be accurate in localizing the infection foci and determining the activity of the inflammatory processes.
2. 99mTc-depreotide tumour uptake in patients with non-Hodgkin's lymphoma
David L Bushnell, Yusuf Menda, Mark T Madsen, Brian K Link, Daniel Kahn, Scott M Truhlar, Malik Juweid, Mary Shannon, Jeffrey S Murguia Nucl Med Commun. 2004 Aug;25(8):839-43. doi: 10.1097/01.mnm.0000126628.01919.f9.
Background: 99mTc-depreotide (NeoTect) is a synthetic somatostatin analogue, which binds to somatostatin receptor (SSTR) subtypes 2, 3 and 5. Imaging patients with non-Hodgkin's lymphoma (NHL) using the somatostatin analogue In-pentetreotide (Octreoscan) has demonstrated the feasibility of identifying lymphoma sites with this class of peptide radiopharmaceutical. SSTR peptides can be labelled with beta emitters and, if sufficient tumour uptake relative to normal organs can be demonstrated, therapeutic applications can be considered. Methods: In this prospective Institutional Review Board (IRB)-approved study, patients with NHL and a recent computed tomography (CT) examination were eligible. Whole-body and selected single-photon emission computed tomography (SPECT) imaging was performed 1 h after intravenous injection of 99mTc-depreotide. Images were compared with CT scan findings. The radioactivity concentration of 99mTc-depreotide in abdominal/pelvic tumour sites, together with normal organs, was determined and expressed as the percentage of injected activity per gram of tissue (%IA x g). Results: Paired CT and 99mTc-depreotide images for three patients with indolent and six with aggressive NHL revealed abnormal 99mTc-depreotide uptake corresponding to the tumour seen on CT in seven of these patients. In three of the patients, all known tumour sites were detected on 99mTc-depreotide images. The mean %IA x g for nine abdominal/pelvic tumour foci from four patients was found to be 0.004% (range, 0.001-0.007%). The mean tumour to bone marrow activity concentration ratio in these four patients was found to be 0.94 (range, 0.33-1.40), whereas the tumour to kidney ratio was 0.53 (range, 0.16-0.80). Conclusions: Levels of 99mTc-depreotide in tumour suggest at least the possibility of potential therapy with beta emitter-labelled SSTR peptides; however, depreotide itself appears not to be a suitable candidate as a targeting agent due to the relatively high bone marrow concentration.
3. Somatostatin receptor imaging of non-small cell lung cancer with 99mTc depreotide
Yusuf Menda, Daniel Kahn Semin Nucl Med. 2002 Apr;32(2):92-6. doi: 10.1053/snuc.2002.31564.
Several tumors overexpress somatostatin receptors (SSTR) and can thus be imaged with radiolabeled analogues of somatostatin. Tc-99m depreotide is a new radiolabeled somatostatin analogue that shows high affinity for SSTR2, SSTR3, and SSTR5 subtypes. It has been recently FDA-approved for use in the evaluation of indeterminate solitary pulmonary nodules. SPECT with Tc-99m depreotide is highly accurate in this clinical setting and may be preferable to FDG-PET because of its lower cost and wider availability. Large studies are also underway to evaluate the accuracy of Tc-99m depreotide in staging of lung cancer.
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