Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid - Publikacja - MOST Wiedzy

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Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid

Abstrakt

Mycophenolic acid (MPA) was coupled with amino acids and biologically active peptides including derivatives of tuftsin to modify its immunosuppressive properties. Both amino acid unit in the case of simple MPA amides and modifications within peptide moiety of MPA - tuftsin conjugates influenced the observed activity. Antiproliferative potential of the obtained conjugates was investigated in vitro and MPA amides with threonine methyl ester and conjugate of MPA with retro-tuftisin occurred to be more selective against PBMC in comparison to parent MPA. Both amino acid and peptide derivatives of MPA acted as inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitors.

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Kategoria:
Publikacja w czasopiśmie
Typ:
artykuły w czasopismach
Opublikowano w:
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY nr 189, strony 1 - 17,
ISSN: 0223-5234
Język:
angielski
Rok wydania:
2020
Opis bibliograficzny:
Siebert A., Cholewiński G., Trzonkowski P., Rachoń J.: Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY -Vol. 189, (2020), s.1-17
DOI:
Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1016/j.ejmech.2020.112091
Bibliografia: test
  1. CNMR (400 MHz,CD3OD-d4) δ ppm: 10.06 (e), 14.98 (f), 18.98 (γ-T4), 22.31 (d), 24.66 (γ-K4), 28.30 (γ-P4), 29.22 (γ-R4), 31.00 (β-R3), 31.96 (β-A3), 33.95 (δ-K5), 35.06 (β-P3), 36.06 (α-A2), 38.66 (β-K3), 40.56 (h), 42.151 (g), 46.868 (ε-K6), 48.332 (δ-R5) 50.85 (δ-P5), 51.48 (α-R2), 53.29 (OMe), 56.93 (α-K2), 57.81 (α-T2), 60.18 (c), 67.01 (β-T3), 69.37 (b), 106.37 (o), 116.03 (l), 122.37 (r), 123.12 (a), 133.63 (j), 145.31 (m), 159.56 (p), 163.42 (k), 170.96 (n), 170.99 (T1), 172.51 (P1), 172.98 (i) 173.26 (K1), 174.24 (R1,A1); otwiera się w nowej karcie
  2. 2.2.2.5. Compound MPA-Arg(NO2)-Pro-Lys(Val)-Thr-OMe 3l: Product 3l was obtained with yield 79% as white powder. otwiera się w nowej karcie
  3. MPA-RT-Val 3l: 1 HNMR (400 MHz, DMSO-d6) δ ppm: 0.807 (d, J=6.9 Hz, 3H, γ-V4), 0.858 (d, J=6.8 Hz, 3H, δ-V5), 1.026 (d, J=4.2 Hz, 3H, γ-T4), 1.279 (m, 2H, γ-K4), 1.369 (m, 3H, δ-K5, β-R3b), 1.461 (m, 3H, β-K3b, γ-R4), 1.627 (m, 2H, β-K3a, β-R3a), 1.714 (s, 3H, f), 1.792 (m, 2H, γ-P4b, β-P3b), 1.861 (m, 2H, γ-P4a, β-V3), 1.977 (m, 1H, β-P3a), 2.061 (s, 3H, e), 2.114 (m, 2H, g), 2.183 (m, 2H, h), 3.005 (m, 5H, α-V2, ε-K6, δ-R5), 3.262 (d, J=6.7 Hz, 2H, d), 3.502 (m, 1H, δ-P5b), 3.604 (m, 1H, δ-P5a), 3.625 (s, 3H, COOMe), 3.676 (s, 3H, c), 4.096 (m, 1H, β-T3), 4.252 (m, 1H, α-T2), 4.269 (m, 1H, α-K2), 4.3 (m, 1H, α-P2), 4.437 (m, 1H, α-R2), 5.096 (t, J=6,5 Hz, 1H, a), 5.222 (s, 2H, b), 7.803 (d, J=8.4 Hz, 1H, α-TNH), 8.022 (m, 3H, α-RNH, α-KNH, ε-KNH);
  4. CNMR (400 MHz,CD3OD-d4) δ ppm: 10.05 (e), 14.96 (f), 16.99 (δ-V5), 18.22 (γ-V4), 18.97 (γ-T4), 22.28 (d), 24.65 (γ-K4), 28.49 (γ-P4), 29.22 (γ-R4), 31.05 (β-R3), 31.56 (β-V3), 33.96 (δ-K5), 35.07 (β-P3), 38.68 (β-K3), 40.53 (h), 42.16 (g), 46.648 (ε-K6), 47.904 (δ-R5) 50.74 (δ-P5), 51.46 (α-R2), 53.33 (OMe), 56.93 (α-T2), 57.80 (α-V2), 60.1 (α-P2), 60.18 (c), 67.01 (β-T3), 69.39 (b), 106.35 (o), 116.26 (l), 122.3 (r), 123.08 (a), 133.67 (j), 145.28 (m), 159.57 (p), 163.42 (k), 170.98 (n), 171.12 (T1), 172.43 (P1), 172.97 (i) 173.22 (K1), 173.41 (R1), 174.21 (V1); otwiera się w nowej karcie
  5. 2.2.2.6. Compound MPA-Arg(NO2)-Pro-Lys(Leu)-Thr-OMe 3m: Product 3m was obtained with yield 91% as white powder. otwiera się w nowej karcie
  6. MPA-RT-Leu 3m: 1 HNMR (400 MHz, DMSO-d6) δ ppm: 0.77 (m, 6H, δ -L5, ε-L6), 1.014 (m, 3H, γ-T4), 1.22 (m, 10H, γ-K4, β-L3b, β-L3a, δ-K5, β-R3b, β-K3b, γ-R4), 1.59 (m, 3H, β-K3a, β-R3a, γ-L4b), 1.69 (s, 3H, f), 1.79 (m, 3H, γ-P4b, β-P3b, γ-L4a), 1.98 (m, 1H, γ-P4a), 2.05 (s, 3H, e), 2.11 (m, 4H, g, h), 3.03 (m, 2H, ε-K6), 3.11 (m, 2H, δ-R5), 3.25 (d, 2H, J=6.2
  7. Hz, d), 3.32 (m, 1H, α-L2), 3.52 (m, 2H, δ-P5b, δ-P5a), 3.60 (s, 3H, COOMe), 3.67 (s, 3H, c), 4.09 (m, 1H, β-T3), 4.24 (m, 2H, α-T2, α-K2), 4.32 (m, 1H, α-P2), 4.43 (m, 1H, α-R2), 5.10 (t, J=6.6 Hz, 1H, a), 5.21 (s, 2H, b), 7.82 (d, J=8.4 Hz, 1H, α-TNH), 8.08 (m, 2H, α-RNH, α-KNH), 8.12 (m, 1H, ε-KNH);
  8. CNMR (400 MHz,CD3OD-d4) δ ppm: 11.49 (e), 16.44 (f), 20.48 (γ-T4), 23.39 (d/γ-K4), 23.35 (δ-L5), 24.41 (γ-L4), 24.87 (γ-P4/γ-R4), 28.83 (β-R3), 29.17 (δ-K5), 29.52 (β-P3), 31.81 (β-K3), 34.25 (h), 35.48 (g), 38.81 (ε-K6), 40.54 (δ-R5) 43.17 (β-L3), 47.18 (δ-P5), 50.26 (α-R2), 52.28 (OMe), 52.74 (α-L2) 52.85 (α-K2), 58.13 (α-T2), 59.58 (α-P2), 60.95 (c), 66.76 (β-T3), 68.98 (b), 122.94 (o/a), 146.11 (m), 159.72 (p), 162.98 (k), 170.48 (n), 171.43 (T1), 171.82 (P1), 172.14 (i) 172.59 (K1); otwiera się w nowej karcie
  9. 2.2.2.7. Compound MPA-Arg(NO2)-Pro-Lys(Ile)-Thr-OMe 3n: Product 3n was obtained with yield 84% as white powder. otwiera się w nowej karcie
  10. MPA-RT-Ile 3n: 1 HNMR (400 MHz, DMSO-d6) δ ppm: 0.806 (m, 6H, δ-I5, ε-I6), 1.041 (d, J=6.3 Hz, 3H, γ-T4), 1.078 (m, 2H, γ-I4), 1.273 (m, 2H, γ-K4), 1.393 (m, 3H, δ-K5, β-R3b), 1.459 (m, 3H, β-K3b, γ-R4), 1.634 (m, 3H, β-K3a, β-R3a, β-I3), 1.727 (s, 3H, f), 1.804 (m, 2H, γ-P4b, β-P3b), 1.894 (m, 2H, γ-P4a, β-T3), 1.995 (m, 1H, β-P3a), 2.071 (s, 3H, e), 2.129 (m, 4H, g, h), 3.007 (m, 5H, α-I2, ε-K6, δ-R5), 3.272 (d, J=6.5 Hz, 2H, d), 3.515 (m, 1H, δ-P5b), 3.617 (m, 1H, δ-P5a), 3.625 (s, 3H, COOMe), 3.687 (s, 3H, c), 4.103 (m, 1H, β-T3), 4.25 (m, 2H, α-T2, α-K2), 4.339 (m, 1H, α-P2), 4.444 (m, 1H, α-R2), 5.142 (t, J=6.7 Hz, 1H, a), 5.228 (s, 2H, b), 7.817 (d, J=8.2 Hz, 1H, α-TNH), 8.018 (m, 3H, α-RNH, α-KNH, ε-KNH);
  11. CNMR (400 MHz,CD3OD-d4) δ ppm: 10.07 (e), 10.45 (δ-I5), 14.45 (ε-I6), 14.93 (f), 18.97 (γ-T4), 22.29 (d), 24.22 (γ-I4), 24.66 (γ-K4), 28.48 (γ-P4), 29.22 (γ-R4), 31.04 (β-R3), 33.97 (δ-K5), 35.08 (β-P3), 38.24 (β-I3), 38.69 (β-K3), 40.53 (h), 42.16 (g), 46.894 (ε-K6), 48.357 (δ-R5) 50.76 (δ-P5), 51.47 (α-R2), 53.35 (OMe), 56.93 (α-T2), 57.81 (α-I2), 59.08 (α-K2), 60.11 (α-P2), 60.18 (c), 67.02 (β-T3), 69.39 (b), 106.35 (o), 116.2 (l), 122.32 (r), 123.09 (a), 133.66 (j), 145.29 (m), 159.56 (p), 163.42 (k), 170.99 (n), 171.14 (T1), 172.45 (P1), 172.97 (i) 173.23 (K1), 173.42 (R1), 174.21 (I1); otwiera się w nowej karcie
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Weryfikacja:
Politechnika Gdańska

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