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Photo-Trimethyl-Lock
Nom chimique: 3-(2-Nitroveratryl-4,6-dimethylphenyl)-3-methylbutyric acid
- n° Art.:RL-2970
- n° CAS:2095134-25-9
- Formule:C22H27NO7
- Masse moléculaire:417,45 g/mol
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description
The trimethyl-lock concept is a new methodology to mask and inactivate active compounds and activate them by specific conditions. The traceless release of compounds protected with this TML derivative can be triggered by photolytic cleavage.
A wide range of applications already has been published, like prodrug and drug release, use as self immolative spacer or in biomolecular imaging.
references
Syntheses and kinetic studies of cyclisation-based self-immolative spacers; Steve Huvelle, Ahmed Alouane, Thomas Le Saux, Ludovic Jullien, and Frédéric Schmidt; Org. Biomol. Chem.
2017; 15: 3435-3443. DOI: 10.1039/c7ob00121e
Trimethyl lock: a trigger for molecular release in chemistry, biology, and pharmacology; Michael N. Levine and Ronald T. Raines; Chem. Sci. 2012; 3: 2412-2420. DOI:
10.1039/c2sc20536j
Syntheses and kinetic studies of cyclisation-based self-immolative spacers; Steve Huvelle, Ahmed Alouane, Thomas Le Saux, Ludovic Jullien and Frédéric Schmidt; Org. Biomol. Chem.
2017; 15: 3435-3443. DOI: 10.1039/C7OB00121E
Self-Immolative Spacers: Kinetic Aspects, Structure-Property Relationships, and Applications; Ahmed Alouane, Raphaël Labruère, Thomas Le Saux, Frédéric Schmidt, and Ludovic
Jullien; Angew. Chem. Int. Ed. 2015; 54: 7492-7509. DOI: 10.1002/anie.201500088
Fluorogenic Label for Biomolecular Imaging; Luke D. Lavis, Tzu-Yuan Chao, and Ronald T. Raines; ACS Chem. Biol. 2006; 1(4): 252-260. DOI: 10.1021/cb600132m
Prodrug Strategies Based on Intramolecular Cyclization Reactions; Daxian Shan, Michalis G. Nicolaou, Ronald T. Borchardt, and Binghe Wang; J. Pharm. Sci. 1997; 86(7): 765-767.
DOI: S0022-3549(97)00069-5
Drug Delivery Systems Based on Trimethyl Lock Lactonization: Poly(ethylene glycol) Prodrugs of Amino-Containing Compounds; Richard B. Greenwald, Yun H. Choe, Charles D. Conover,
Kwok Shum, Dechun Wu, and Maksim Royzen; J. Med. Chem. 2000; 43: 475-487. DOI: 10.1021/jm990498j
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