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[ CAS No. 137076-54-1 ] {[proInfo.proName]}

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Chemical Structure| 137076-54-1
Chemical Structure| 137076-54-1
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Ajay Kumar Sharma ; Kuldeep Gupta ; Akhilesh Mishra , et al. DOI:

Abstract: The limited availability of molecularly targeted low-molecular-weight imaging agents for monitoring multiple myeloma (MM)-targeted therapies has been a significant challenge in the field. In response, a first-in-class peptide-based radiotracer, [68Ga]Ga-AJ206, is developed that can be seamlessly integrated into the standard clinical workflow and is specifically designed to noninvasively quantify levels and pharmacodynamics by positron emission tomography (PET). A bicyclic , AJ206, is synthesized and exhibits high affinity to (KD: 19.1 ± 0.99 × 10?9 m) by surface plasmon resonance. Further, [68Ga]Ga-AJ206-PET shows high contrast within 60 min and suitable absorbed dose estimates for clinical use. Additionally, [68Ga]Ga-AJ206 detects expression in cell line-derived xenografts, patient-derived xenografts (PDXs), and disseminated disease models in a manner consistent with flow cytometry and immunohistochemistry findings. Moreover, [68Ga]Ga-AJ206-PET successfully quantifies pharmacodynamics in PDXs, revealing increased expression in the tumor following all-trans (ATRA) therapy. In conclusion, [68Ga]Ga-AJ206 exhibits the salient features required for clinical translation, providing CD38-specific high-contrast images in multiple models of MM. [68Ga]Ga-AJ206-PET could be useful for quantifying total levels and pharmacodynamics during therapy to evaluate approved and new therapies in MM and other diseases with involvement.

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Astrid Haraldsson ;

Abstract: One of the major challenges in cancer treatment is delivering high enough doses of active substance specifically to cancer cells without accumulation in healthy organs. Pretargeting has emerged as a potential solution, where the delivery of a cancer recognizing (primary) agent and a cancer killing (secondary) agent are separated. Pretargeted cancer therapy utilizing PNA probes has proved to be a promising approach to selectively deliver toxic payloads to cancer cells while minimizing accumulation in healthy organs. The aim of this project was to develop a new set of secondary PNA probes specifically designed for PNA pretargeted delivery of cytotoxic drugs. A HER2-specific Affibody molecule, ZHER2:2891-SR-H6, was recombinantly produced in E. coli before being conjugated to a primary PNA hybridization probe, HP9, through sortase A-mediated ligation, to produce the primary agent, ZHER2:2891-SR-HP9. Circular dichroism (CD) spectroscopy confirmed the stability of the constructs with high melting temperatures of 71.2 and 73.7 °C. Surface plasmon resonance (SPR) analysis demonstrated high binding affinity to HER2, slightly affected by PNA conjugation. Three new secondary PNA hybridization probes were designed, differing mainly in prevalence and position of a hydrophilic PEG molecule. The probes were produced by solid phase peptide synthesis and conjugated to the cytotoxic drug DM1 through maleimide-cysteine coupling. Analytical RP-HPLC evaluation revealed a slightly higher apparent hydrophobicity for the probe with PEG in the main chain. All three secondary probes displayed high affinity to the primary probe with KD values between 498–505 pM. In vitro cytotoxicity studies on HER2-overexpressing cells demonstrated comparable potent cytotoxic activity for pre-incubated primary and secondary probes with IC50 values of 10–14 nM. These results indicate the successful development of three PNA-drug conjugates for pretargeted delivery of cytotoxic drugs.

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Product Details of [ 137076-54-1 ]

CAS No. :137076-54-1 MDL No. :MFCD02259697
Formula : C28H52N4O8 Boiling Point : -
Linear Structure Formula :N4C8H16(CH2COOC(CH3)3)3CH2COOH InChI Key :RVUXZXMKYMSWOM-UHFFFAOYSA-N
M.W : 572.73 Pubchem ID :11606627
Synonyms :
Chemical Name :2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid

Safety of [ 137076-54-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 137076-54-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 137076-54-1 ]

[ 137076-54-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 35661-40-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 71989-28-1 ]
  • [ 104091-08-9 ]
  • [ 143824-78-6 ]
  • [ 137076-54-1 ]
  • [ 1306310-02-0 ]
  • 2
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 35661-40-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 77284-32-3 ]
  • [ 104091-08-9 ]
  • [ 143824-78-6 ]
  • [ 137076-54-1 ]
  • DOTA-DGlu-Ala-Tyr-Gly-Trp-Nle-Asp-Phe-NH<SUB>2</SUB>, Nle=norleucine, DOTA=1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid [ No CAS ]
  • 3
  • 9-fluorenylmethoxycarbonyl-O-methyl-L-homoserine [ No CAS ]
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 35661-40-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 104091-08-9 ]
  • [ 143824-78-6 ]
  • [ 137076-54-1 ]
  • DOTA-[Mox]15(human minigastrin) [ No CAS ]
  • 4
  • Fmoc-Ile-Wang resin [ No CAS ]
  • [ 29022-11-5 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 77128-73-5 ]
  • [ 109425-55-0 ]
  • (3aS,7aS)-octahydroindole-2-carboxylic acid [ No CAS ]
  • N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 137076-54-1 ]
  • C82H124N18O21 [ No CAS ]
  • 5
  • Fmoc-Lys(ivDde)-Wang resin [ No CAS ]
  • [ 27913-58-2 ]
  • C14H23NO5 [ No CAS ]
  • [ 167690-53-1 ]
  • [ 137076-54-1 ]
  • C67H95IN12O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Fmoc-Lys(ivDde)-Wang resin (0.3 mmol, 0.61 mmol/g loading) was suspended in DMF for 30 mm. Fmoc was then removed by treating the resin with 20% piperidine in DMF (3 x 8 mm). The isocyanate derivative of di-t-butyl ester of glutamate (3 eq.) was prepared according to literatureprocedures,17 and added to the lysine-immobilized resin and reacted for 16 h. After washing the resinwith DMF, the ivDde-protecting group was removed with 2% hydrazine in DMF (5 x 5 mi. Fmoc-2- Nal-OH was then coupled to the side chain of Lys followed by Fmoc-tranexamic acid, FmocLys(ivDde)-OH, and Fmoc-Gly-OH via solid-phase peptide synthesis using Fmoc-based chemistry. Allcouplings were carried out in DMF using Fmoc-protected amino acid (3 eq.), HBTU (3 eq.), HOBT (3eq.), and DIEA (8 eq.). Afterwards, elongation was continued with the addition of <strong>[27913-58-2]4-<strong>[27913-58-2](p-iodophenyl)butyric acid</strong></strong> (for HTK03024), 4-(p-chlorophenyl)butyric acid (for HTK03055), 4-phenylbutyric acid (for HTK03056), 4-(p-bromophenyl)butyric acid (for HTK03058), 3-phenyipropanoic acid (for HTK03082), 4-(p-fluorophenyl)butyric acid (for HTK03085), 4-(p-methoxyphenyl)butyric acid(for HTK03086), 4-(p-(t-butyloxycarbonyl)aminophenyl)butyric acid (for HTK03087), 4-(p-nitrophenyl)butyric acid (for HTK03089), or 4-(p-tolyl)butyric acid (for HTKO3O9O) were coupled to thesame peptide-bound resin using Fmoc-based chemistry. After selective removal of the ivDdeprotecting group with 2% hydrazine in DMF (5 x 5 mm), the chelator DOTA was then coupled to theside chain of Lys to give the precursors. The peptide was then deprotected and simultaneously cleaved from the resin by treatingwith 95/5 trifluoroacetic acid (TFA)/triisopropylsilane (TIS) for 2 h at room temperature. After filtration,the peptide was precipitated by the addition of cold diethyl ether to the TFA solution. The crude peptide was purified by HPLC using the semi-preparative column. The eluates containing the desired peptidewere collected, pooled, and lyophilized. For HTK03024, the HPLC conditions were 37% acetonitrile inwater with 0.1% TFA at a flow rate of 4.5 mL/min. The retention time was 8.8 mi ESI-MS: calculated[M+H] for HTK03024 C67H96N120191 1499.6; found [M+H] 1499.6. For HTK03055, the HPLCconditions were 35% acetonitrile in water with 0.1% TFA at a flow rate of 4.5 mL/min. The retentiontime was 9.7 mi ESI-MS: calculated [M+H] for HTK03055 C67H96N12019C1 1407.7; found [M+H]1407.7. For HTK03056, the HPLC conditions were 0-80% acetonitrile in waterwith 0.1% TFA ata flowrate of 4.5 mL/min in 20 mm. The retention time was 13.4 mi ESI-MS: calculated [M+H] forHTK03056 C67H97N12019 1373.7; found [M+H] 1373.8. For HTK03058, the HPLC conditions were 0-80% acetonitrile in water with 0.1% TFA at a flow rate of 4.5 mL/min in 20 mm. The retention time was13.4 mi ESI-MS: calculated [M+H] for HTK03058 C67H96N12O19Br 1451.6; found [M+H] 1451.6. ForHTK03082, the HPLC conditions were 31% acetonitrile in water with 0.1% TFA at a flow rate of 4.5mL/min. The retention time was 11.1 mi ESI-MS: calculated [M+H] for HTK03082 C66H95N120191359.7; found [M+H] 1359.9. For HTK03085, the HPLC conditions were 34% acetonitrile in waterwith0.1% TFA at a flow rate of 4.5 mL/min. The retention time was 9.0 mi ESI-MS: calculated [M+H] forHTK03085 C67H96N12019F 1391.7; found [M+H] 1391.9. For HTK03086, the HPLC conditions were33% acetonitrile in water with 0.1% TFA at a flow rate of 4.5 mL/min. The retention time was 9.1 mm.ESI-MS: calculated [M+H] for HTK03086 C68H99N12020 1403.7; found [M+H] 1404.1. For HTK03087,the HPLC conditions were 23% acetonitrile in water with 0.1% TFA ata flow rate of 4.5 mL/min. Theretention time was 13.9 mi ESI-MS: calculated [M+H] for HTK03087 C67H98N13019 1388.7; found[M+H] 1389.0. For HTK03089, the HPLC conditions were 33% acetonitrile in water with 0.1% TFA ataflow rate of 4.5 mL/min. The retention time was 10.6 mi ESI-MS: calculated [M+H] for HTK03089C67H96N13021 1418.7; found [M+H] 1419.0. For HTKO3O9O, the HPLC conditions were 35% acetonitrile in water with 0.1% TFA at a flow rate of 4.5 mL/min. The retention time was 9.1 mm. ESI-MS:calculated [M+H] for HTKO3O9O C68H99N12019 1387.7; found [M+H] 1387.9.
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