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Volumn 59, Issue 5, 2004, Pages 345-352

Modulation of cytokine production by some phthalimido-desmuramyl dipeptides and their cytotoxicity

Author keywords

Cytokines; Cytotoxic activity; Muramyl dipeptide analogues; Phthalimido desmuramyldipeptides; Synthesis

Indexed keywords

CYTOKINE; GAMMA INTERFERON; IMMUNOMODULATING AGENT; INTERLEUKIN 10; INTERLEUKIN 12; INTERLEUKIN 2; INTERLEUKIN 4; IONOMYCIN; LK 413; LK 508; LK 511; LK 512; LK 517; MURAMYL DIPEPTIDE DERIVATIVE; N (5 PHTHALIMIDOPENTANOYL) DEXTRO ALANYL DEXTRO ISOGLUTAMINE; PEPTIDOGLYCAN; PHORBOL 13 ACETATE 12 MYRISTATE; UNCLASSIFIED DRUG;

EID: 2142779123     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2004.01.003     Document Type: Article
Times cited : (11)

References (53)
  • 1
    • 0016200846 scopus 로고
    • Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives
    • Ellouz F., Adam A., Cirobaru R., Lederer E. Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives. Biochem. Biophys. Res. Commun. 59:1974;1317-1325
    • (1974) Biochem. Biophys. Res. Commun. , vol.59 , pp. 1317-1325
    • Ellouz, F.1    Adam, A.2    Cirobaru, R.3    Lederer, E.4
  • 2
    • 0022647082 scopus 로고
    • Multiplicity of biological efects of muramyl dipeptide
    • Mašek K. Multiplicity of biological efects of muramyl dipeptide. Methods Find. Exp. Clin. Pharmacol. 8:1986;97-99
    • (1986) Methods Find. Exp. Clin. Pharmacol. , vol.8 , pp. 97-99
    • Mašek, K.1
  • 3
    • 0022978898 scopus 로고
    • Immunological activities of muramyl peptides
    • Bahr G.M., Chedid L. Immunological activities of muramyl peptides. Fed. Proc. 45:1986;2541-2544
    • (1986) Fed. Proc. , vol.45 , pp. 2541-2544
    • Bahr, G.M.1    Chedid, L.2
  • 4
    • 0018957559 scopus 로고
    • Central pyrogenic activity of muramyl dipeptide
    • Riveau G., Mašek K., Parant M., Chedid L. Central pyrogenic activity of muramyl dipeptide. J. Exp. Med. 152:1980;869-877
    • (1980) J. Exp. Med. , vol.152 , pp. 869-877
    • Riveau, G.1    Mašek, K.2    Parant, M.3    Chedid, L.4
  • 6
    • 0028229633 scopus 로고
    • Potentiation of host defense mechanism against infection by a cytokine inducer, an acyl-MDP derivative, MDP-Lys(L18) (Romurtide) in mice and humans
    • Azuma I., Otani T. Potentiation of host defense mechanism against infection by a cytokine inducer, an acyl-MDP derivative, MDP-Lys(L18) (Romurtide) in mice and humans. Med. Res. Rev. 14:1994;401-414
    • (1994) Med. Res. Rev. , vol.14 , pp. 401-414
    • Azuma, I.1    Otani, T.2
  • 8
    • 0021324968 scopus 로고
    • Muramyl peptides: Immunomodulators, sleep factors and vitamins
    • Adam A., Lederer E. Muramyl peptides: immunomodulators, sleep factors and vitamins. Med. Res. Rev. 4:1984;111-152
    • (1984) Med. Res. Rev. , vol.4 , pp. 111-152
    • Adam, A.1    Lederer, E.2
  • 9
    • 0024452645 scopus 로고
    • Muramylpeptides and lipopeptides: Studies toward immunostimulants
    • Baschang G. Muramylpeptides and lipopeptides: studies toward immunostimulants. Tetrahedron. 45:1989;6331-6360
    • (1989) Tetrahedron , vol.45 , pp. 6331-6360
    • Baschang, G.1
  • 11
    • 0019802735 scopus 로고
    • Total synthesis of FK-156 isolated from a Streptomyces as an immunostimulating peptide: Application of a novel copper chelate amino protection
    • Hemmi K., Takeno H., Okada S., Nakaguchi O., Kitaura Y., Hashimoto M. Total synthesis of FK-156 isolated from a Streptomyces as an immunostimulating peptide: application of a novel copper chelate amino protection. J. Am. Chem. Soc. 103:1981;7026-7028
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7026-7028
    • Hemmi, K.1    Takeno, H.2    Okada, S.3    Nakaguchi, O.4    Kitaura, Y.5    Hashimoto, M.6
  • 13
    • 0029845471 scopus 로고    scopus 로고
    • The influence of the lipophilicity of the 7-oxoacyl-L-alanyl-D- isoglutamines on their immunorestoration activity in vivo
    • Sollner M., Pečar S., Štalc A. The influence of the lipophilicity of the 7-oxoacyl-L-alanyl-D-isoglutamines on their immunorestoration activity in vivo. Eur. J. Med. Chem. 31:1996;927-933
    • (1996) Eur. J. Med. Chem. , vol.31 , pp. 927-933
    • Sollner, M.1    Pečar, S.2    Štalc, A.3
  • 14
    • 0024373521 scopus 로고
    • Synthesis of biologically active carbocyclic analogues of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP)
    • Barton D.H.R., Camara J., Dalko P., Gero S.D. Synthesis of biologically active carbocyclic analogues of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP). J. Org. Chem. 54:1989;3764-3766
    • (1989) J. Org. Chem. , vol.54 , pp. 3764-3766
    • Barton, D.H.R.1    Camara, J.2    Dalko, P.3    Gero, S.D.4
  • 15
    • 0034935443 scopus 로고    scopus 로고
    • Synthesis and modulation of cytokine production by two new adamantane substituted acyclic desmuramyldipeptide analogs
    • Gobec S., Urleb U., Simčič S., Wraber B. Synthesis and modulation of cytokine production by two new adamantane substituted acyclic desmuramyldipeptide analogs. Pharmazie. 56:2001;523-526
    • (2001) Pharmazie , vol.56 , pp. 523-526
    • Gobec, S.1    Urleb, U.2    Simčič, S.3    Wraber, B.4
  • 16
    • 0004705992 scopus 로고
    • Immunosupression by thalidomide?
    • Dukor P., Dietrich F.M. Immunosupression by thalidomide? Lancet. 1:1967;569-570
    • (1967) Lancet , vol.1 , pp. 569-570
    • Dukor, P.1    Dietrich, F.M.2
  • 17
    • 0031052074 scopus 로고    scopus 로고
    • Immunomodulatory assays to study structure-activity relationships of thalidomide
    • Shannon E.J., Morales M.J., Sandoval F. Immunomodulatory assays to study structure-activity relationships of thalidomide. Immunopharmacology. 35:1997;203-212
    • (1997) Immunopharmacology , vol.35 , pp. 203-212
    • Shannon, E.J.1    Morales, M.J.2    Sandoval, F.3
  • 18
    • 0028568261 scopus 로고
    • TNF alpha regulation of HIV-1: Biology and therapy
    • Kaplan G., Moreira A.L. TNF alpha regulation of HIV-1: Biology and therapy. Res. Immunol. 145:1994;685-689
    • (1994) Res. Immunol. , vol.145 , pp. 685-689
    • Kaplan, G.1    Moreira, A.L.2
  • 19
    • 0031837706 scopus 로고    scopus 로고
    • Novel biological response modifiers derived from thalidomide
    • Hashimoto Y. Novel biological response modifiers derived from thalidomide. Curr. Med. Chem. 5:1998;163-178
    • (1998) Curr. Med. Chem. , vol.5 , pp. 163-178
    • Hashimoto, Y.1
  • 21
    • 0018596740 scopus 로고
    • Studies on the derivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid. I. Synthesis and pharmacological analysis of acylderivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid
    • Jacobiec T., Glama I., Kowlaczyk-Bromisz S.H., Stankiewicz J., Zawisza T. Studies on the derivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid. I. Synthesis and pharmacological analysis of acylderivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid. Arch. Immunol. Ther. Exp. 27:1979;777-794
    • (1979) Arch. Immunol. Ther. Exp. , vol.27 , pp. 777-794
    • Jacobiec, T.1    Glama, I.2    Kowlaczyk-Bromisz, S.H.3    Stankiewicz, J.4    Zawisza, T.5
  • 22
    • 25944478649 scopus 로고
    • Aziridine carboxylic acid derivatives, Ger. Offen. 2740,248, 15 Mar 1977
    • Bosies E., Heerdt R., Gall R., Bicker U., Ziegler A.E. Aziridine carboxylic acid derivatives, Ger. Offen. 2740, 248, 15 Mar 1977. Chem. Abstr. 90:1979;203849q
    • (1979) Chem. Abstr. , vol.90
    • Bosies, E.1    Heerdt, R.2    Gall, R.3    Bicker, U.4    Ziegler, A.E.5
  • 23
    • 0028957692 scopus 로고
    • Synthesis of phthalimido-desmuramylpeptide analogues as potential immunomodulating agents
    • Urleb U., Krbavčič A., Sollner M., Kikelj D., Pečar S. Synthesis of phthalimido-desmuramylpeptide analogues as potential immunomodulating agents. Arch. Pharm. (Weinheim). 328:1995;113-117
    • (1995) Arch. Pharm. (Weinheim) , vol.328 , pp. 113-117
    • Urleb, U.1    Krbavčič, A.2    Sollner, M.3    Kikelj, D.4    Pečar, S.5
  • 25
    • 0033058550 scopus 로고    scopus 로고
    • Therapeutic effects of LK 423, a phthalimido-desmuramyldipeptide compound, on dextran sulphate sodium-induced colitis in rodents through restoring their interleukin-10 producing capacity
    • Moriguchi M., Urabe K., Norisada N., Ochi C., Štalc A., Urleb U., Muraoka S. Therapeutic effects of LK 423, a phthalimido-desmuramyldipeptide compound, on dextran sulphate sodium-induced colitis in rodents through restoring their interleukin-10 producing capacity. Arzneim.-Forsch./Drug Res. 49:1999;184-192
    • (1999) Arzneim.-Forsch./Drug Res. , vol.49 , pp. 184-192
    • Moriguchi, M.1    Urabe, K.2    Norisada, N.3    Ochi, C.4    Štalc, A.5    Urleb, U.6    Muraoka, S.7
  • 26
    • 0033833904 scopus 로고    scopus 로고
    • Modulation of tumor necrosis factor production with desmuramyldipeptide analogues
    • Simčič S., Wraber B., Sollner M., Urleb U., Gobec S. Modulation of tumor necrosis factor production with desmuramyldipeptide analogues. Pflug. Arch. Eur. J. Phy. 440:2000;R64-R66
    • (2000) Pflug. Arch. Eur. J. Phy. , vol.440 , pp. 64-R66
    • Simčič, S.1    Wraber, B.2    Sollner, M.3    Urleb, U.4    Gobec, S.5
  • 27
    • 0000123376 scopus 로고
    • Synthesis and activity of phosphono desmuramyldipeptide analogs
    • Urleb U., Gobec S., Prelog D. Synthesis and activity of phosphono desmuramyldipeptide analogs. Lett. Pept. Sci. 2:1995;193-197
    • (1995) Lett. Pept. Sci. , vol.2 , pp. 193-197
    • Urleb, U.1    Gobec, S.2    Prelog, D.3
  • 28
    • 0001536815 scopus 로고    scopus 로고
    • Synthesis of new phosphonamidate and phosphinamide desmuramyldipeptide analogs
    • Gobec S., Urleb U. Synthesis of new phosphonamidate and phosphinamide desmuramyldipeptide analogs. Lett. Pept. Sci. 5:1998;109-114
    • (1998) Lett. Pept. Sci. , vol.5 , pp. 109-114
    • Gobec, S.1    Urleb, U.2
  • 29
    • 0034338141 scopus 로고    scopus 로고
    • Synthesis of phosphono phthalimido-desmuramyldipeptide analogs
    • Gobec S., Urleb U. Synthesis of phosphono phthalimido-desmuramyldipeptide analogs. Phosphorus, Sulfur, Silicon Relat. Elem. 156:2000;125-133
    • (2000) Phosphorus, Sulfur, Silicon Relat. Elem. , vol.156 , pp. 125-133
    • Gobec, S.1    Urleb, U.2
  • 30
    • 0037601266 scopus 로고    scopus 로고
    • Synthesis of new lipophilic phosphonate and phosphonamidate analogues of N-acetylmuramyl-L-alanyl-D-isoglutamine related to LK 423
    • Gobec S., Urleb U. Synthesis of new lipophilic phosphonate and phosphonamidate analogues of N-acetylmuramyl-L-alanyl-D-isoglutamine related to LK 423. Molecules. 7:2002;394-404
    • (2002) Molecules , vol.7 , pp. 394-404
    • Gobec, S.1    Urleb, U.2
  • 31
    • 0032249333 scopus 로고    scopus 로고
    • Influence of immunomodulators of the type MDP on secrecion and activity of cytokines
    • Dzierzbicka K., Godowska M., Kolodziejczyk A.M. Influence of immunomodulators of the type MDP on secrecion and activity of cytokines. Postepy Biochem. 44:1998;216-219
    • (1998) Postepy Biochem. , vol.44 , pp. 216-219
    • Dzierzbicka, K.1    Godowska, M.2    Kolodziejczyk, A.M.3
  • 32
    • 0028245845 scopus 로고
    • Differences in interleukin-1 (IL-1), IL-6, tumor-necrosis-factor and IL-1 receptor antagonist production by human monocytes stimulated with muramyl dipeptide (MDP) and its stearoyl derivative, romurtide
    • Suzuki K., Torii K., Hida S., Hayashi H., Hiyama Y., Oomoto Y., Takii T., Chiba T., Onozaki K. Differences in interleukin-1 (IL-1), IL-6, tumor-necrosis-factor and IL-1 receptor antagonist production by human monocytes stimulated with muramyl dipeptide (MDP) and its stearoyl derivative, romurtide. Immunopharmacology. 28:1994;31-38
    • (1994) Immunopharmacology , vol.28 , pp. 31-38
    • Suzuki, K.1    Torii, K.2    Hida, S.3    Hayashi, H.4    Hiyama, Y.5    Oomoto, Y.6    Takii, T.7    Chiba, T.8    Onozaki, K.9
  • 33
    • 0030032209 scopus 로고    scopus 로고
    • Synergistic effects between recombinant interleukin-2 and the synthetic immunomodulator murabutide: Selective enhancement of cytokine release and potentiation of antitumor activity
    • Bahr G.M., Darcissac E., Pouillart P.R., Chedid L.A. Synergistic effects between recombinant interleukin-2 and the synthetic immunomodulator murabutide: Selective enhancement of cytokine release and potentiation of antitumor activity. J. Interferon Cytokine Res. 16:1996;169-178
    • (1996) J. Interferon Cytokine Res. , vol.16 , pp. 169-178
    • Bahr, G.M.1    Darcissac, E.2    Pouillart, P.R.3    Chedid, L.A.4
  • 34
    • 0032855210 scopus 로고    scopus 로고
    • ImmTher, a lipophilic disaccharide derivative of muramyl dipeptide, up-regulates specific monocyte cytokine genes and activates monocyte-mediated tumoricidal activity
    • Worth L.L., Jia S.F., An T., Kleinerman E.S. ImmTher, a lipophilic disaccharide derivative of muramyl dipeptide, up-regulates specific monocyte cytokine genes and activates monocyte-mediated tumoricidal activity. Cancer Immunol. Immunother. 48:1999;312-320
    • (1999) Cancer Immunol. Immunother. , vol.48 , pp. 312-320
    • Worth, L.L.1    Jia, S.F.2    An, T.3    Kleinerman, E.S.4
  • 35
    • 0018220121 scopus 로고
    • Synthesis of 6-O-mycolyl-N-acetyl-muramyl-L-alanyl-D-isoglutamine with antitumor activity
    • Shiba T., Okada S., Kusumoto S., Azuma I., Yamamura Y. Synthesis of 6-O-mycolyl-N-acetyl-muramyl-L-alanyl-D-isoglutamine with antitumor activity. Bull. Chem. Soc. Jpn. 51:1978;3307-3311
    • (1978) Bull. Chem. Soc. Jpn. , vol.51 , pp. 3307-3311
    • Shiba, T.1    Okada, S.2    Kusumoto, S.3    Azuma, I.4    Yamamura, Y.5
  • 36
    • 0018069909 scopus 로고
    • Synthesis of long chain fatty acid esters of N-acetyl-muramyl-L-alanyl-D- isoglutamine in relation to anti-tumor activity
    • Kusumoto S., Inage M., Shiba T., Azuma I., Yamamura Y. Synthesis of long chain fatty acid esters of N-acetyl-muramyl-L-alanyl-D-isoglutamine in relation to anti-tumor activity. Tetrahedron Lett. 49:1978;4895-4899
    • (1978) Tetrahedron Lett. , vol.49 , pp. 4895-4899
    • Kusumoto, S.1    Inage, M.2    Shiba, T.3    Azuma, I.4    Yamamura, Y.5
  • 38
    • 0035950163 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramylpeptides with acridine/acridone derivatives
    • Dzierzbicka K., Kolodziejczyk A.M., Wysocka-Skrzela B., Myśliwski A., Sosnowska D. Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramylpeptides with acridine/acridone derivatives. J. Med. Chem. 44:2001;3606-3615
    • (2001) J. Med. Chem. , vol.44 , pp. 3606-3615
    • Dzierzbicka, K.1    Kolodziejczyk, A.M.2    Wysocka-Skrzela, B.3    Myśliwski, A.4    Sosnowska, D.5
  • 39
    • 0037413547 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridine/acridone derivatives
    • Dzierzbicka K., Kolodziejczyk A.M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridine/ acridone derivatives. J. Med. Chem. 46:2003;183-189
    • (2003) J. Med. Chem. , vol.46 , pp. 183-189
    • Dzierzbicka, K.1    Kolodziejczyk, A.M.2
  • 40
    • 0037435066 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives
    • Dzierzbicka K., Trzonkowski P., Sewerynek P., Myśliwski A. Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives. J. Med. Chem. 46:2003;978-986
    • (2003) J. Med. Chem. , vol.46 , pp. 978-986
    • Dzierzbicka, K.1    Trzonkowski, P.2    Sewerynek, P.3    Myśliwski, A.4
  • 41
    • 0038070140 scopus 로고    scopus 로고
    • Determination of cytotoxic activity of adamantyl-desmuramyl dipeptides
    • Filipič M., Kuhar P., Žegura B., Urleb U., Gobec S. Determination of cytotoxic activity of adamantyl-desmuramyl dipeptides. Pharmazie. 58:2003;442-443
    • (2003) Pharmazie , vol.58 , pp. 442-443
    • Filipič, M.1    Kuhar, P.2    Žegura, B.3    Urleb, U.4    Gobec, S.5
  • 42
    • 0028954832 scopus 로고
    • Cytotoxicity of imides-N-alkyl semicarbazones, thiosemicarbazones, acetylhydrazones and related derivatives
    • Hall I.H., Wong O.T., Chapmann J.M. Cytotoxicity of imides-N-alkyl semicarbazones, thiosemicarbazones, acetylhydrazones and related derivatives. Anti-Cancer Drugs. 6:1995;147-153
    • (1995) Anti-Cancer Drugs , vol.6 , pp. 147-153
    • Hall, I.H.1    Wong, O.T.2    Chapmann, J.M.3
  • 43
    • 0029135409 scopus 로고
    • The cytotoxicity of N-pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide
    • Hall I.H., Wong O.T., Scovill J.P. The cytotoxicity of N-pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide. Biomed. and Pharmacother. 5:1995;251-258
    • (1995) Biomed. and Pharmacother. , vol.5 , pp. 251-258
    • Hall, I.H.1    Wong, O.T.2    Scovill, J.P.3
  • 44
    • 0035096816 scopus 로고    scopus 로고
    • A study of the anti-invasive properties of N-alpha-phthalimidomethyl- ketomethylene tripeptide-based metalloprotease inhibitors
    • Martin S.L., McDowell A., Lynas J.F., Nelson J., Walker B. A study of the anti-invasive properties of N-alpha-phthalimidomethyl-ketomethylene tripeptide-based metalloprotease inhibitors. J. Pharm. Pharmacol. 53:2001;333-343
    • (2001) J. Pharm. Pharmacol. , vol.53 , pp. 333-343
    • Martin, S.L.1    McDowell, A.2    Lynas, J.F.3    Nelson, J.4    Walker, B.5
  • 46
    • 0029072244 scopus 로고
    • Evaluation of the anticancer property of a new α-methylene-γ- lactone derivative of phthalimide
    • Sanyal U., Dutta S., Das H. Evaluation of the anticancer property of a new α-methylene-γ-lactone derivative of phthalimide. Neoplasma. 42:1995;129-132
    • (1995) Neoplasma , vol.42 , pp. 129-132
    • Sanyal, U.1    Dutta, S.2    Das, H.3
  • 47
    • 84982074419 scopus 로고
    • A simple preparation of phthaloyl amino acids via a mild phthaloylation
    • Nefkens G.H.L., Tesser G.I., Nivard R.J.F. A simple preparation of phthaloyl amino acids via a mild phthaloylation. Rec. Trav. Chim. Pays-Bas. 79:1960;688-698
    • (1960) Rec. Trav. Chim. Pays-Bas , vol.79 , pp. 688-698
    • Nefkens, G.H.L.1    Tesser, G.I.2    Nivard, R.J.F.3
  • 48
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival - Application to proliferation and cyto-toxicity assays
    • Mosmann T. Rapid colorimetric assay for cellular growth and survival - application to proliferation and cyto-toxicity assays. J. Immunol. Meth. 65:1983;55-63
    • (1983) J. Immunol. Meth. , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 52
    • 0031058331 scopus 로고    scopus 로고
    • Cytokines acting on or secreted by macrophages during intracellular infection (IL-10, IL-12, IFN-γ)
    • Trinchieri G. Cytokines acting on or secreted by macrophages during intracellular infection (IL-10, IL-12, IFN-γ). Curr. Opin. Immunol. 9:1997;17-23
    • (1997) Curr. Opin. Immunol. , vol.9 , pp. 17-23
    • Trinchieri, G.1
  • 53
    • 0004149256 scopus 로고    scopus 로고
    • J.J. Oppenheim, & M. Feldmann. San Diego: Academic Press
    • Oppenheim J.J., Feldmann M. Cytokine reference. 2001;Academic Press, San Diego
    • (2001) Cytokine Reference


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