Synthesis of organometallic derivatives and their use as fluorescent and electrochemical markers for peptide nucleic acids
Brevetto
Data di Pubblicazione:
2006
Citazione:
Synthesis of organometallic derivatives and their use as fluorescent and electrochemical markers for peptide nucleic acids / S. Maiorana, C. Baldoli, C. Rigamonti, P.R. Mussini.
Abstract:
Organometallic iron, chromium and tungsten compds. R1A(CH2)nCHa[(CH2)mD(R5XYQ)p]b [1, a+b = 3, provided a<3 and at least in one branch m>0; p = 1, 2; n = 0-5, m = 0-8, preferably n = 0-2, m = 1; R1 = H, CO, CHO, C1-6 alkanedioic monoacyl, carboxyalkylamino, carboxy, carbamoyl, 1-imidazolecarbonyl; A, D = O, N, S; X = C0-5 alkylene, CO, carbamoyl, CO(CH2)1-5, C(O)S; Y = C0-5 alkylene,, (CH2)1-5NHCO, (CH2)1-5SCO; Q = (CO)3Cr(5-C6H5), C:Cr(CO)5, C:W(CO)5, (5-C5H4)Fe(5-C5H5); preferably Q = ferrocenyl, (CO)3Cr(5-C6H5)], useful as electrochem. and fluorescent markers for DNA and RNA bonding with peptide nucleic acids (PNA), were prepd. by stepwise modification of precursors A(CH2)nCHa[(CH2)mD]b with reagents R1-E and E1R5XYQ (E, E1 = leaving groups); or by esterification of A(CH2)nC[(CH2)mN(R5COOH)2]3, followed by amidation or thiolation and attachment of the required organometallic moiety. The prepd. mols. 1 were then bound to the biomols. PNA, DNA or RNA, preferably to PNA, suitably modified for peptide synthesis, mainly for the purposes of diagnostics. In an example, compd. H2NC(CH2OCH2Fc)3 (20; Fc = ferrocenyl) was prepd. by etherification of N-Cbz-tris(hydroxymethyl)methanamine with ferrocenemethanol and subsequent deprotection in 90% yield. In another example, tyrosine PNA monomer was modified by 20 giving 4'-[tris(ferrocenylmethoxymethyl)methyl]carbamoyl deriv. (30). These products are preferably used as labels of biomols. (for example: nucleic acids, oligonucleotides, PNAs, peptides, proteins, steroids etc.) mainly used in the field of diagnostics
Tipologia IRIS:
09 - Brevetto, privativa o norma
Elenco autori:
S. Maiorana, C. Baldoli, C. Rigamonti, P.R. Mussini
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