Cyclens and Their Applications in MRI and RNA Studies
Delve into the world of cyclens and discover their diverse applications in magnetic resonance imaging (MRI) and RNA studies. From their synthesis pathways to functionalization methods, learn how cyclens play a crucial role in advancing medical and scientific research.
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Presentation Transcript
- (Crown ethers) 18 - 6 1. 2. KMnO4 18 - 6 !
Cyclen Aza 12 - 4 : -CH2CH2NH- cyclens: 1. 2. !
1886 Baeyer 1. 1937 Alphen 2. 1953, 1956 Kriissig Greber 3. 1959 Down 6 . 1960 Curtis 5. 1961 Stetter and Mayer 7. 1967 - Pedersen 4. tetraazaquaterene
Cyclens MRI DNA RNA !
2+2 i) ii) THF,RT LiAlH4, THF,RT cyclen (1961) 27% 3+1 DMF 110o C H2SO4 40% 1 90% 2
- cyclen 70 - 90% pyridine 90% 1 80-95% 2 RT
N cyclen Direct N1,N4- or N1,N7-Difunctionalization of Cyclen via Tri- or Tetracyclic Intermediates N,N-cis-Difunctionalization of Cyclen a)BnBr b) 2 chloromethyl pyridine c) n-PrBr d)4-tBuBnBr EtOH + reflux Na2CO3 DMF 100 C NaOH, H2O 90 C 55-77% 66% 96% 1 93 74% 2 81-71% 3
cyclens 1H NMR 13C NMR MS
Magnetic resonance imaging (MRI) 90 FID sequence: : S = kp (1-? ?R ?1) : 1 2 Ln3+ 1 2
Cyclens MRI Ln3+ : Gadoteric acid in vivo MRI ( ), 1 : 0.1 mmol/kg
RNA 5 RNA 5 : 1. mRna 2. mRNA 3. mRNA 5
Cyclens RNA 86% 5 4h - 0.10 mM 37 C pH = 7.4 2+ t1/2: 37 C ( ) Zn(NO3)2 : a-phosphate : GDP and Eu(THED)-GMP 5
(RIT) (42He) 40-100 m - ( ) (e-) 1mm 1cm 0.1 1 keV/ m 100keV/ m DNA
Cyclens H2O [213Bi(Me-do2pa)] NO3 213Bi(NO3)3.5H2O + : ligand (-) t1/2 Bi 212Bi (t1/2=61 min) and 213Bi (t1/2=46 min) 212Pb (t1/2= 10.6 h)
Jerald S. Bradshaw, Krzysztof E. Krakowiak, Reed M. Izatt, AZA CROWN MACROCYCLES, Department of Chemistry Brigham Young University, Provo. Utah 84602-1022 Cong Li and Wing-Tak Wong, Tetrahedron Letters 43 (2002) 3217 3220 Mojm r Such and Robert H. E. Hudson, Eur. J. Org. Chem. 2008, 4847 4865 Silvio Aime, Mauro Botta, oltan Garda, Benjamin E. Kucera, Gyula Tircso, Victor G. Young, and Mark Woods, Inorg. Chem. 2011, 50, 7955 7965 Armando Tartaro,Marica Tina Maccarone, Reports in Medical Imaging 2015:8 25 35 Daniel M. Epstein, Lara L. Chappell, Homayoon Khalili, Ronald M. Supkowski, William DeW. Horrocks, Jr., and Janet R. Morrow, Inorg. Chem. 2000, 39, 2130-2134 Brenda F. Baker, Homayoon Khalili, Ning Wei, and Janet R. Morrow, Jacs ,1997, 119, 38 Luis M. P. Lima, Maryline Beyler, Fatima Oukhatar, Patricia Le Saec, Alain Faivre Chauvet, Carlos Platas-Iglesias, Rita Delgado and Raphael Tripier, Chem. Commun., 2014, 50, 12371-12374 Eric W. Price and Chris Orvig, Chem. Soc. Rev., 2014, 43, 260 290 http://www.chemistry.uoc.gr/milios/teaching.htm
