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Depreotide

Depreotide is a peptide analogue of a somatostatin receptor that preferentially binds to somatostatin receptors 2, 3, and 5. Many lung tumors may express these receptors to a greater extent than normal tissue. Depreotide study is a noninvasive, receptor-specific imaging agent that is used to assess malignant versus benign single pulmonary nodules before biopsy.

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CAT No: 10-101-102

CAS No: 161982-62-3

Synonyms/Alias: NeoTec; P 829; P829; D03687; P-829

Chemical 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;technetium

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC65H96N16O12S2
M.W/Mr.1357.69
SequenceCyclo(L-homocysteinyl-N-methyl-L-phenylalanyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl) (1-1')-sulfide with 3-((mercaptoacetyl)amino)-L-alanyl-L-lysyl-L-cysteinyl-L-lysinamide
Labeling TargetSomatostatin receptor
ApplicationRadiodiagnostic agent
Areas of InterestCancer treatment
Source#Synthetic
Solubility−20°C
InChIInChI=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 KeyXXXSJQLZVNKRKX-YQRDHHIGSA-N
Canonical SMILESCC(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.[Tc]
Isomeric SMILESCC(C)[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)CC5=CC=CC=C5)C)CCSCC(=O)NC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCCN)C(=O)N)N
BoilingPoint1654.2±65.0 °C at 760 mmHg
References

99mTc-depreotide uptake was found in 62 out of 66 malignancies, including 57 of 58 primary lung cancer cases. Two cases of lung metastasis (one from a colon cancer and one from an adenoid cystic carcinoma originating in the palate) and one rib chondrosarcoma did not show depreotide uptake. There were 33 patients with benign lesions, of whom 16 displayed false-positive 99mTc-depreotide uptake, whereof 11 were pneumonias. Tc-99m-depreotide uptake was absent in 17 patients with benign lesions, including all 10 hamartomas. The sensitivity in detecting malignancy was 94%, and in detecting lung cancer 98%. The specificity was calculated based on two sets of data. When all cases were used, the specificity was 52%. If the 12 pneumonias are excluded, the specificity was 77%.

Axelsson, R., Herlin, G., Bååth, M., Aspelin, P., & Kölbeck, K. G. (2008). Role of scintigraphy with technetium-99m depreotide in the diagnosis and management of patients with suspected lung cancer. Acta Radiologica, 49(3), 295-302.

Of 21 patients who had a focal high uptake of Depreotide, 17 were malignancies. One patient had two lesions with high Depreotide uptake, lung cancer, and pneumonia in the contralateral lung. Two patients with sarcoidosis and one with bilateral round atelectasis also had high Depreotide uptake bilaterally. Seven of the 8 patients with no uptake were true negative: 5 hamartomas and 2 round atelectases. One small lung cancer in the pleura sinus did not have Depreotide uptake.

Bååth, M., Kölbeck, K. G., & Danielsson, R. (2004). Somatostatin receptor scintigraphy with 99mTc-Depreotide (NeoSpect) in discriminating between malignant and benign lesions in the diagnosis of lung cancer: a pilot study. Acta Radiologica, 45(8), 833-839.

Tc-depreotide imaging has low sensitivity but is useful in a one-third of OctreoScan-negative patients, displaying significantly better uptake than In-pentetreotide in this patient group. It aids diagnosis by highlighting lesions not seen by OctreoScan and/or CT/MRI imaging, and can possibly identify a group of patients amenable to therapy with radionuclide agents, such as SOM230, targeting somatostatin receptor subtypes 2, 3 and 5.

Shah, T., Kulakiene, I., Quigley, A. M., Warbey, V. S., Srirajaskanthan, R., Toumpanakis, C., ... & Caplin, M. E. (2008). The role of 99mTc-depreotide in the management of neuroendocrine tumours. Nuclear medicine communications, 29(5), 436-440.

Melting PointN/A

1. Constitutive and inflammation-dependent antimicrobial peptides produced by epithelium are differentially processed and inactivated by the commensal Finegoldia magna and the pathogen Streptococcus pyogenes

2. High fat diet and GLP-1 drugs induce pancreatic injury in mice

3. Crystal Structure of BamB from Pseudomonas aeruginosa and Functional Evaluation of Its Conserved Structural Features

4. The effect of sex on immune responses to a homocitrullinated peptide in the DR4-transgenic mouse model of Rheumatoid Arthritis

5. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

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