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Organic Letters
Volumn 11, Issue 12, 2009, Pages 2479-2482
Solid-phase synthetic strategy and bioevaluation of a labeled δ-opioid receptor ligand Dmt-Tic-Lys for In Vivo imaging
Author keywords

[No Author keywords available]
Indexed keywords

CARBOCYANINE; CYANINE DYE 5; DELTA OPIATE RECEPTOR; DIAGNOSTIC AGENT; FLUORESCENT DYE; ISOQUINOLINE DERIVATIVE; LIGAND;
EID: 67149116788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900200k     Document Type: Article
Times cited : (24)
References (39)
  • 26
    • 67149140667 scopus 로고    scopus 로고
    • Calculated log D of compound 1 reveals a value of 1.01 at pH 7.4 (log D: 2.6. 1.35. 1.16 at pH 1.5. 5.0, 6.5, respectively)
    • (a) Calculated log D of compound 1 reveals a value of 1.01 at pH 7.4 (log D: 2.6. 1.35. 1.16 at pH 1.5. 5.0, 6.5, respectively)
  • 28
    • 84869000246 scopus 로고    scopus 로고
    • In a 50 mL bottle containing 1 g of Wang resin (0.93 mmol/g) with a magnetic stir bar, dry CH2C12 was added to swell the resin for 1 h. The solvent was removed, the bottle closed with a septum and flushed with nitrogen, and ιPr2NEt (9 equiv, 1.4 mL) in 15 mL of CH 2Cl2 was added. The resin slurry was cooled to 0 °C followed by dropwise addition of MsCl (8 equiv, 0.57 mL) in 2 mL of CH 2C12. The reaction was stirred for 20 min, the ice-bath was removed, and the stirring was continued for another 20 min (rt, The resin was then transferred to a syringe reactor and washed with dry CH 2C12 and dry DMF. Fmoc-Lys(Mtt)-OH (2 equiv, 1.2g, Csl (2 equiv, 6.5g, ιPr2NEt (2 equiv, 0.32 mL) in ca. 10 mL of dry DMF were added, and the reaction was stirred overnight at rt
    • 2NEt (2 equiv, 0.32 mL) in ca. 10 mL of dry DMF were added, and the reaction was stirred overnight at rt.
  • 29
    • 84868962828 scopus 로고    scopus 로고
    • 2, 0.2 M HOBt/DMF, and DMF. Fmoc-Tic-OH (3 equiv), HOCt (3 equiv), and DIC (6 equiv) in DMF were then added, and the reaction was stirred for 2 h.
    • 2, 0.2 M HOBt/DMF, and DMF. Fmoc-Tic-OH (3 equiv), HOCt (3 equiv), and DIC (6 equiv) in DMF were then added, and the reaction was stirred for 2 h.
  • 31
    • 84868965363 scopus 로고    scopus 로고
    • 2NEt (6 equiv) in DMF were added to the resin, and the reaction was heated in a household microwave for 3 s. The reaction was stirred until it cooled to rt; the heating was repeated (5x), and the resin was stirried for another 2 h.
    • 2NEt (6 equiv) in DMF were added to the resin, and the reaction was heated in a household microwave for 3 s. The reaction was stirred until it cooled to rt; the heating was repeated (5x), and the resin was stirried for another 2 h.
  • 32
    • 67149126110 scopus 로고    scopus 로고
    • Ligand 8 was dissolved in HEPES buffer (pH 7.2), and 1.3 equiv of Cy5-maleimide was added in aliquots until full conversion was achieved as monitored on analytical HPLC. The labeled ligand was then separated with SPE (see Supporting Information).
    • Ligand 8 was dissolved in HEPES buffer (pH 7.2), and 1.3 equiv of Cy5-maleimide was added in aliquots until full conversion was achieved as monitored on analytical HPLC. The labeled ligand was then separated with SPE (see Supporting Information).
  • 33
    • 84868996518 scopus 로고    scopus 로고
    • 2.
    • 2.
  • 34
    • 67149110491 scopus 로고    scopus 로고
    • The reaction stirred overnight in inert atmosphere (to prevent disulfide formation by air oxidation)
    • The purified compound was dissolved in (NH4) 2CO3/NF4OAC buffer (pH 8) and 3 equiv of EuCl3-6H2O was added, Supporting Information
    • 2O was added. The reaction stirred overnight in inert atmosphere (to prevent disulfide formation by air oxidation). The excess salts were then removed by solid-phase extraction (SPE) (see Supporting Information).
    • The excess salts were then removed by solid-phase extraction (SPE) (see
  • 35
    • 0028077859 scopus 로고    scopus 로고
    • No diketopiperazine formation was observed in this solvent system for 1 month; see: Carpenter, K. A.; Weltrowska, G.; Wilkes, B. C.; Schmidt, R.; Schiller, P. W. J. An. Chem. Soc. 1994, 116, 8450-8458.
    • No diketopiperazine formation was observed in this solvent system for 1 month; see: Carpenter, K. A.; Weltrowska, G.; Wilkes, B. C.; Schmidt, R.; Schiller, P. W. J. An. Chem. Soc. 1994, 116, 8450-8458.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.