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DOTA-TATE

September 01, 2023

DOTA-TATE (DOTATATE,[1] DOTA-octreotate, oxodotreotide, DOTA-(Tyr3)-octreotate,[2] and DOTA-0-Tyr3-Octreotate) is an eight amino acid long peptide, with a covalently bonded DOTA bifunctional chelator.

DOTA-TATE
Names
Other names
DOTA-(Tyr3)-octreotate
Identifiers
  • 177943-89-4 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9345959
  • 11170867
UNII
  • 99R86Y6V0M Y
  • DTXSID60170399
  • InChI=1S/C65H90N14O19S2/c1-38(80)56-64(96)73-51(63(95)75-57(39(2)81)65(97)98)37-100-99-36-50(72-59(91)47(28-40-10-4-3-5-11-40)68-52(83)32-76-20-22-77(33-53(84)85)24-26-79(35-55(88)89)27-25-78(23-21-76)34-54(86)87)62(94)70-48(29-41-15-17-43(82)18-16-41)60(92)71-49(30-42-31-67-45-13-7-6-12-44(42)45)61(93)69-46(58(90)74-56)14-8-9-19-66/h3-7,10-13,15-18,31,38-39,46-51,56-57,67,80-82H,8-9,14,19-30,32-37,66H2,1-2H3,(H,68,83)(H,69,93)(H,70,94)(H,71,92)(H,72,91)(H,73,96)(H,74,90)(H,75,95)(H,84,85)(H,86,87)(H,88,89)(H,97,98)/t38-,39-,46+,47-,48+,49-,50+,51+,56+,57+/m1/s1
    Key: QVFLVLMYXXNJDT-CSBVGUNJSA-N
  • InChI=1/C65H90N14O19S2/c1-38(80)56-64(96)73-51(63(95)75-57(39(2)81)65(97)98)37-100-99-36-50(72-59(91)47(28-40-10-4-3-5-11-40)68-52(83)32-76-20-22-77(33-53(84)85)24-26-79(35-55(88)89)27-25-78(23-21-76)34-54(86)87)62(94)70-48(29-41-15-17-43(82)18-16-41)60(92)71-49(30-42-31-67-45-13-7-6-12-44(42)45)61(93)69-46(58(90)74-56)14-8-9-19-66/h3-7,10-13,15-18,31,38-39,46-51,56-57,67,80-82H,8-9,14,19-30,32-37,66H2,1-2H3,(H,68,83)(H,69,93)(H,70,94)(H,71,92)(H,72,91)(H,73,96)(H,74,90)(H,75,95)(H,84,85)(H,86,87)(H,88,89)(H,97,98)/t38-,39-,46+,47-,48+,49-,50+,51+,56+,57+/m1/s1
    Key: QVFLVLMYXXNJDT-CSBVGUNJBN
  • C[C@H]([C@H]1C(=O)N[C@@H](CSSC[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)NC(=O)[C@@H](CC5=CC=CC=C5)NC(=O)CN6CCN(CCN(CCN(CC6)CC(=O)O)CC(=O)O)CC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)O
Properties
C65H90N14O19S2
Molar mass 1435.63 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

DOTA-TATE can be reacted with the radionuclides gallium-68 (T1/2 = 68 min), lutetium-177 (T1/2 = 6.65 d) and copper-64 (T1/2 = 12.7 h) to form radiopharmaceuticals for positron emission tomography (PET) imaging or radionuclide therapy. 177Lu DOTA-TATE therapy is a form of peptide receptor radionuclide therapy (PRRT) which targets somatostatin receptors (SSR).[3][4] In that form of application it is a form of targeted drug delivery.

Chemistry and mechanism of action Edit

DOTA-TATE is a compound containing tyrosine3-octreotate,[2] an SSR agonist, and the bifunctional chelator DOTA (tetraxetan).[5][6] SSRs are found with high density in numerous malignancies, including CNS, breast, lung, and lymphatics.[7] The role of SSR agonists (i.e. somatostatin and its analogs such as octreotide, somatuline and vapreotide) in neuroendocrine tumours (NETs) is well established,[8] and massive SSR overexpression is present in several NETs. (Tyr3)-octreotate binds the transmembrane receptors of NETs with highest activity for SSR2 and is actively transported into the cell via endocytosis, allowing trapping of the radioactivity and increasing the probability of the desired double-strand DNA breakage (for tumour control). Trapping improves the probability of this kind of effect due to the relatively short range of the beta particles emitted by 177Lu, which have a maximum range in tissue of <2 mm.[9][8][10] Bystander effects include cellular damage by free radical formation.

Clinical applications Edit

Gallium-68 DOTA-TATE Edit

Further information: Gallium scan § Gallium DOTA scans

68Ga DOTA-TATE (gallium-68 dotatate, GaTate) is used to measure tumor SSR density and whole-body bio-distribution via PET imaging.[11][12] 68Ga DOTA-TATE imagery has a much higher sensitivity and resolution compared to 111In octreotide gamma camera or SPECT scans, due to intrinsic modality differences.[11]

Copper-64 DOTA-TATE Edit

Copper (64Cu) oxodotreotide or copper Cu 64 dotatate, sold under the brand name Detectnet, is a radioactive diagnostic agent indicated for use with positron emission tomography (PET) for localization of somatostatin receptor positive neuroendocrine tumors (NETs) in adults. It was FDA approved in September 2020. These are the same indications for as the gallium DOTA-TATE scans, but Cu-64 has advantages over Ga-68 in having a 12-hour half life rather than the much shorter one-hour half life of Ga-68, making it easier to transport from central production locations. [13][14]

Lutetium-177 DOTA-TATE Edit

Main article: Lutetium (177Lu) oxodotreotide
See also: peptide receptor radionuclide therapy

The combination of the beta emitter 177Lu with DOTA-TATE can be used in the treatment of cancers expressing the relevant somatostatin receptors.[15] The U.S. Food and Drug Administration (FDA) considers 177Lu-dotatate to be a first-in-class medication.[16]

Alternatives to 177Lu-DOTA-TATE include 90Y (T1/2 = 64.6 h) DOTA-TATE. The longer penetration range in the target tissues of the more energetic beta particles emitted by 90Y (high average beta energy of 0.9336 MeV) could make it more suitable for large tumors while 177Lu would be preferred for smaller volume tumors.[17][18]

See also Edit

References Edit

  1. ^ Nockel P, Millo C, Keutgen X, Klubo-Gwiezdzinska J, Shell J, Patel D, Nilubol N, Herscovitch P, Sadowski SM, Kebebew E (June 2016). "The Rate and Clinical Significance of Incidental Thyroid Uptake as Detected by Gallium-68 DOTATATE Positron Emission Tomography/Computed Tomography". Thyroid. 26 (6): 831–5. doi:10.1089/thy.2016.0174. PMC 4913484. PMID 27094616.
  2. ^ a b Pubchem. "[Tyr3]octreotate". pubchem.ncbi.nlm.nih.gov. Retrieved 2 April 2018.
  3. ^ Papotti, M.; Herder, W. W. de (2015). Neuroendocrine Tumors: A Multidisciplinary Approach. Karger Medical and Scientific Publishers. p. 77. ISBN 9783318027730.
  4. ^ Aktolun, Cumali; Goldsmith, Stanley J. (2012). Nuclear Medicine Therapy: Principles and Clinical Applications. Springer. p. 364. ISBN 9781461440215.
  5. ^ Pubchem. "Tetraxetan". pubchem.ncbi.nlm.nih.gov. Retrieved 2 April 2018.
  6. ^ Fani M, Nicolas GP, Wild D (September 2017). "Somatostatin Receptor Antagonists for Imaging and Therapy". Journal of Nuclear Medicine. 58 (Suppl 2): 61S–66S. doi:10.2967/jnumed.116.186783. PMID 28864614.
  7. ^ Reubi JC, Laissue JA (March 1995). "Multiple actions of somatostatin in neoplastic disease". Trends in Pharmacological Sciences. 16 (3): 110–5. doi:10.1016/S0165-6147(00)88992-0. PMID 7792931.
  8. ^ a b Mazziotti G, Mosca A, Frara S, Vitale G, Giustina A (November 2017). "Somatostatin analogs in the treatment of neuroendocrine tumors: current and emerging aspects". Expert Opinion on Pharmacotherapy. 18 (16): 1679–1689. doi:10.1080/14656566.2017.1391217. PMID 29067877. S2CID 46747267.
  9. ^ Emmett L, Willowson K, Violet J, Shin J, Blanksby A, Lee J (March 2017). "177 PSMA radionuclide therapy for men with prostate cancer: a review of the current literature and discussion of practical aspects of therapy". Journal of Medical Radiation Sciences. 64 (1): 52–60. doi:10.1002/jmrs.227. PMC 5355374. PMID 28303694.
  10. ^ Reubi JC, Schonbrunn A (December 2013). "Illuminating somatostatin analog action at neuroendocrine tumor receptors". Trends in Pharmacological Sciences. 34 (12): 676–88. doi:10.1016/j.tips.2013.10.001. PMC 3883302. PMID 24183675.
  11. ^ a b Hofman MS, Kong G, Neels OC, Eu P, Hong E, Hicks RJ (February 2012). "High management impact of Ga-68 DOTATATE (GaTate) PET/CT for imaging neuroendocrine and other somatostatin expressing tumours". Journal of Medical Imaging and Radiation Oncology. 56 (1): 40–7. doi:10.1111/j.1754-9485.2011.02327.x. PMID 22339744. S2CID 21843609.
  12. ^ Breeman WA, de Blois E, Sze Chan H, Konijnenberg M, Kwekkeboom DJ, Krenning EP (July 2011). "(68)Ga-labeled DOTA-peptides and (68)Ga-labeled radiopharmaceuticals for positron emission tomography: current status of research, clinical applications, and future perspectives". Seminars in Nuclear Medicine. 41 (4): 314–321. doi:10.1053/j.semnuclmed.2011.02.001. PMID 21624565.
  13. ^ "FDA approval letter" (PDF). 3 September 2020. Retrieved 5 September 2020.   This article incorporates text from this source, which is in the public domain.
  14. ^ "RadioMedix and Curium Announce FDA Approval of Detectnet (copper Cu 64 dotatate injection) in the U.S." (Press release). Curium. 8 September 2020. Retrieved 9 September 2020 – via GlobeNewswire.
  15. ^ Wang L, Tang K, Zhang Q, Li H, Wen Z, Zhang H, Zhang H (2013). "Somatostatin receptor-based molecular imaging and therapy for neuroendocrine tumors". BioMed Research International. 2013: 102819. doi:10.1155/2013/102819. PMC 3784148. PMID 24106690.
  16. ^ New Drug Therapy Approvals 2018 (PDF). U.S. Food and Drug Administration (FDA) (Report). January 2019. Retrieved 16 September 2020.
  17. ^ Ramage JK, Ahmed A, Ardill J, Bax N, Breen DJ, Caplin ME, et al. (January 2012). "Guidelines for the management of gastroenteropancreatic neuroendocrine (including carcinoid) tumours (NETs)". Gut. 61 (1): 6–32. doi:10.1136/gutjnl-2011-300831. PMC 3280861. PMID 22052063.
  18. ^ Bodei L, Mueller-Brand J, Baum RP, Pavel ME, Hörsch D, O'Dorisio MS, O'Dorisio TM, O'Dorisiol TM, Howe JR, Cremonesi M, Kwekkeboom DJ, Zaknun JJ (May 2013). "The joint IAEA, EANM, and SNMMI practical guidance on peptide receptor radionuclide therapy (PRRNT) in neuroendocrine tumours". European Journal of Nuclear Medicine and Molecular Imaging. 40 (5): 800–16. doi:10.1007/s00259-012-2330-6. PMC 3622744. PMID 23389427.

September 01, 2023
dota, tate, dotatate, dota, octreotate, oxodotreotide, dota, tyr3, octreotate, dota, tyr3, octreotate, eight, amino, acid, long, peptide, with, covalently, bonded, dota, bifunctional, chelator, namesother, names, dota, tyr3, octreotateidentifierscas, number, 1. DOTA TATE DOTATATE 1 DOTA octreotate oxodotreotide DOTA Tyr3 octreotate 2 and DOTA 0 Tyr3 Octreotate is an eight amino acid long peptide with a covalently bonded DOTA bifunctional chelator DOTA TATE NamesOther names DOTA Tyr3 octreotateIdentifiersCAS Number 177943 89 4 Y3D model JSmol Interactive imageChemSpider 9345959PubChem CID 11170867UNII 99R86Y6V0M YCompTox Dashboard EPA DTXSID60170399InChI InChI 1S C65H90N14O19S2 c1 38 80 56 64 96 73 51 63 95 75 57 39 2 81 65 97 98 37 100 99 36 50 72 59 91 47 28 40 10 4 3 5 11 40 68 52 83 32 76 20 22 77 33 53 84 85 24 26 79 35 55 88 89 27 25 78 23 21 76 34 54 86 87 62 94 70 48 29 41 15 17 43 82 18 16 41 60 92 71 49 30 42 31 67 45 13 7 6 12 44 42 45 61 93 69 46 58 90 74 56 14 8 9 19 66 h3 7 10 13 15 18 31 38 39 46 51 56 57 67 80 82H 8 9 14 19 30 32 37 66H2 1 2H3 H 68 83 H 69 93 H 70 94 H 71 92 H 72 91 H 73 96 H 74 90 H 75 95 H 84 85 H 86 87 H 88 89 H 97 98 t38 39 46 47 48 49 50 51 56 57 m1 s1Key QVFLVLMYXXNJDT CSBVGUNJSA NInChI 1 C65H90N14O19S2 c1 38 80 56 64 96 73 51 63 95 75 57 39 2 81 65 97 98 37 100 99 36 50 72 59 91 47 28 40 10 4 3 5 11 40 68 52 83 32 76 20 22 77 33 53 84 85 24 26 79 35 55 88 89 27 25 78 23 21 76 34 54 86 87 62 94 70 48 29 41 15 17 43 82 18 16 41 60 92 71 49 30 42 31 67 45 13 7 6 12 44 42 45 61 93 69 46 58 90 74 56 14 8 9 19 66 h3 7 10 13 15 18 31 38 39 46 51 56 57 67 80 82H 8 9 14 19 30 32 37 66H2 1 2H3 H 68 83 H 69 93 H 70 94 H 71 92 H 72 91 H 73 96 H 74 90 H 75 95 H 84 85 H 86 87 H 88 89 H 97 98 t38 39 46 47 48 49 50 51 56 57 m1 s1Key QVFLVLMYXXNJDT CSBVGUNJBNSMILES C C H C H 1C O N C H CSSC 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 NC O C H CC5 CC CC C5 NC O CN6CCN CCN CCN CC6 CC O O CC O O CC O O C O N C H C H C O C O O OPropertiesChemical formula C 65H 90N 14O 19S 2Molar mass 1435 63 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references DOTA TATE can be reacted with the radionuclides gallium 68 T1 2 68 min lutetium 177 T1 2 6 65 d and copper 64 T1 2 12 7 h to form radiopharmaceuticals for positron emission tomography PET imaging or radionuclide therapy 177Lu DOTA TATE therapy is a form of peptide receptor radionuclide therapy PRRT which targets somatostatin receptors SSR 3 4 In that form of application it is a form of targeted drug delivery Contents 1 Chemistry and mechanism of action 2 Clinical applications 2 1 Gallium 68 DOTA TATE 2 2 Copper 64 DOTA TATE 2 3 Lutetium 177 DOTA TATE 3 See also 4 ReferencesChemistry and mechanism of action EditDOTA TATE is a compound containing tyrosine3 octreotate 2 an SSR agonist and the bifunctional chelator DOTA tetraxetan 5 6 SSRs are found with high density in numerous malignancies including CNS breast lung and lymphatics 7 The role of SSR agonists i e somatostatin and its analogs such as octreotide somatuline and vapreotide in neuroendocrine tumours NETs is well established 8 and massive SSR overexpression is present in several NETs Tyr3 octreotate binds the transmembrane receptors of NETs with highest activity for SSR2 and is actively transported into the cell via endocytosis allowing trapping of the radioactivity and increasing the probability of the desired double strand DNA breakage for tumour control Trapping improves the probability of this kind of effect due to the relatively short range of the beta particles emitted by 177Lu which have a maximum range in tissue of lt 2 mm 9 8 10 Bystander effects include cellular damage by free radical formation Clinical applications EditGallium 68 DOTA TATE Edit Further information Gallium scan Gallium DOTA scans 68Ga DOTA TATE gallium 68 dotatate GaTate is used to measure tumor SSR density and whole body bio distribution via PET imaging 11 12 68Ga DOTA TATE imagery has a much higher sensitivity and resolution compared to 111In octreotide gamma camera or SPECT scans due to intrinsic modality differences 11 Copper 64 DOTA TATE Edit Copper 64Cu oxodotreotide or copper Cu 64 dotatate sold under the brand name Detectnet is a radioactive diagnostic agent indicated for use with positron emission tomography PET for localization of somatostatin receptor positive neuroendocrine tumors NETs in adults It was FDA approved in September 2020 These are the same indications for as the gallium DOTA TATE scans but Cu 64 has advantages over Ga 68 in having a 12 hour half life rather than the much shorter one hour half life of Ga 68 making it easier to transport from central production locations 13 14 Lutetium 177 DOTA TATE Edit Main article Lutetium 177Lu oxodotreotide See also peptide receptor radionuclide therapy The combination of the beta emitter 177Lu with DOTA TATE can be used in the treatment of cancers expressing the relevant somatostatin receptors 15 The U S Food and Drug Administration FDA considers 177Lu dotatate to be a first in class medication 16 Alternatives to 177Lu DOTA TATE include 90Y T1 2 64 6 h DOTA TATE The longer penetration range in the target tissues of the more energetic beta particles emitted by 90Y high average beta energy of 0 9336 MeV could make it more suitable for large tumors while 177Lu would be preferred for smaller volume tumors 17 18 See also EditLutetium 64Cu dotatateReferences Edit Nockel P Millo C Keutgen X Klubo Gwiezdzinska J Shell J Patel D Nilubol N Herscovitch P Sadowski SM Kebebew E June 2016 The Rate and Clinical Significance of Incidental Thyroid Uptake as Detected by Gallium 68 DOTATATE Positron Emission Tomography Computed Tomography Thyroid 26 6 831 5 doi 10 1089 thy 2016 0174 PMC 4913484 PMID 27094616 a b Pubchem Tyr3 octreotate pubchem ncbi nlm nih gov Retrieved 2 April 2018 Papotti M Herder W W de 2015 Neuroendocrine Tumors A Multidisciplinary Approach Karger Medical and Scientific Publishers p 77 ISBN 9783318027730 Aktolun Cumali Goldsmith Stanley J 2012 Nuclear Medicine Therapy Principles and Clinical Applications Springer p 364 ISBN 9781461440215 Pubchem Tetraxetan pubchem ncbi nlm nih gov Retrieved 2 April 2018 Fani M Nicolas GP Wild D September 2017 Somatostatin Receptor Antagonists for Imaging and Therapy Journal of Nuclear Medicine 58 Suppl 2 61S 66S doi 10 2967 jnumed 116 186783 PMID 28864614 Reubi JC Laissue JA March 1995 Multiple actions of somatostatin in neoplastic disease Trends in Pharmacological Sciences 16 3 110 5 doi 10 1016 S0165 6147 00 88992 0 PMID 7792931 a b Mazziotti G Mosca A Frara S Vitale G Giustina A November 2017 Somatostatin analogs in the treatment of neuroendocrine tumors current and emerging aspects Expert Opinion on Pharmacotherapy 18 16 1679 1689 doi 10 1080 14656566 2017 1391217 PMID 29067877 S2CID 46747267 Emmett L Willowson K Violet J Shin J Blanksby A Lee J March 2017 177 PSMA radionuclide therapy for men with prostate cancer a review of the current literature and discussion of practical aspects of therapy Journal of Medical Radiation Sciences 64 1 52 60 doi 10 1002 jmrs 227 PMC 5355374 PMID 28303694 Reubi JC Schonbrunn A December 2013 Illuminating somatostatin analog action at neuroendocrine tumor receptors Trends in Pharmacological Sciences 34 12 676 88 doi 10 1016 j tips 2013 10 001 PMC 3883302 PMID 24183675 a b Hofman MS Kong G Neels OC Eu P Hong E Hicks RJ February 2012 High management impact of Ga 68 DOTATATE GaTate PET CT for imaging neuroendocrine and other somatostatin expressing tumours Journal of Medical Imaging and Radiation Oncology 56 1 40 7 doi 10 1111 j 1754 9485 2011 02327 x PMID 22339744 S2CID 21843609 Breeman WA de Blois E Sze Chan H Konijnenberg M Kwekkeboom DJ Krenning EP July 2011 68 Ga labeled DOTA peptides and 68 Ga labeled radiopharmaceuticals for positron emission tomography current status of research clinical applications and future perspectives Seminars in Nuclear Medicine 41 4 314 321 doi 10 1053 j semnuclmed 2011 02 001 PMID 21624565 FDA approval letter PDF 3 September 2020 Retrieved 5 September 2020 nbsp This article incorporates text from this source which is in the public domain RadioMedix and Curium Announce FDA Approval of Detectnet copper Cu 64 dotatate injection in the U S Press release Curium 8 September 2020 Retrieved 9 September 2020 via GlobeNewswire Wang L Tang K Zhang Q Li H Wen Z Zhang H Zhang H 2013 Somatostatin receptor based molecular imaging and therapy for neuroendocrine tumors BioMed Research International 2013 102819 doi 10 1155 2013 102819 PMC 3784148 PMID 24106690 New Drug Therapy Approvals 2018 PDF U S Food and Drug Administration FDA Report January 2019 Retrieved 16 September 2020 Ramage JK Ahmed A Ardill J Bax N Breen DJ Caplin ME et al January 2012 Guidelines for the management of gastroenteropancreatic neuroendocrine including carcinoid tumours NETs Gut 61 1 6 32 doi 10 1136 gutjnl 2011 300831 PMC 3280861 PMID 22052063 Bodei L Mueller Brand J Baum RP Pavel ME Horsch D O Dorisio MS O Dorisio TM O Dorisiol TM Howe JR Cremonesi M Kwekkeboom DJ Zaknun JJ May 2013 The joint IAEA EANM and SNMMI practical guidance on peptide receptor radionuclide therapy PRRNT in neuroendocrine tumours European Journal of Nuclear Medicine and Molecular Imaging 40 5 800 16 doi 10 1007 s00259 012 2330 6 PMC 3622744 PMID 23389427 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title DOTA TATE amp oldid 1154166409, wikipedia, wiki, book, books, library,

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