Recent developments in the synthesis and biological activity of muramylpeptides

Current Medicinal Chemistry

Volumn 18, Issue 16, 2011, Pages 2438-2451

  Dzierzbicka, K ^a   Wardowska, A ^b   Trzonkowski, P ^b  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Adjuvant; Cancer immunotherapy; Innate immunity; MDP; MDP analogues; Muramyl dipeptide; Synthesis

Indexed keywords

2 EPIMURAMYLDIPEPTIDE; ALBENDAZOLE; ALPHA INTERFERON; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; CASPASE RECRUITMENT DOMAIN PROTEIN 15; CGP 19835 A; CISPLATIN; CYTOKINE; CYTOSTATIC AGENT; CYTOTOXIC AGENT; DOXORUBICIN; FLUOROURACIL; FOLINIC ACID; IFOSFAMIDE; IMMUNOLOGICAL ADJUVANT; IMMUNOMODULATING AGENT; IMMUNOSTIMULATING AGENT; METHOTREXATE; MIFAMURTIDE; MURAMYL PEPTIDE; MURAMYL PEPTIDE DERIVATIVE; MURAMYL PEPTIDE PACLITAXEL; MUROCTASIN; N ACETYLGLUCOSAMINYL BETA1 4 N ACETYLMURAMYLALANYL DEXTRO ISOGLUTAMINE; N ACETYLMURAMYLALANYL DEXTRO ISOGLUTAMINEGLYCEROL DIPALMITATE; N2 [(N ACETYLMURAMYL)ALANYL DEXTRO ISOGLUTAMINYL] N6 STEAROYLLYSINE; PACLITAXEL; PEPTIDE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER IMMUNOTHERAPY; DRUG POTENTIATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ECHINOCOCCOSIS; HUMAN; IMMUNE SYSTEM; INFECTION; LUNG METASTASIS; MELANOMA; NONHUMAN; OSTEOSARCOMA; PROTEIN DOMAIN; PROTEIN EXPRESSION;

ACETYLMURAMYL-ALANYL-ISOGLUTAMINE; ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; COMMUNICABLE DISEASES; HUMANS; MOLECULAR CONFORMATION; NEOPLASMS;

EID: 79957943310     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986711795843173     Document Type: Article

References (84)

1. Ellouz, F.; Adam, A.; Ciorbaru, R.; Lederer, E. Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives. Biochem. Biophys. Res. Commun., 1974, 59, 1317-1325.
2. Lefrancier, P.; Choay, J.; Derrien, M.; Lederman, I. Synthesis of Nacetylmuramyl- L- alanyl-D-isoglutamine, an adjuvant of the immune response and some N-acetylmuramyl peptide analogs. Int. J. Pept. Protein Res., 1977, 9, 249-257. (Pubitemid 8081226)
3. Adam, A.; Devys, M.; Souvannavong, V.; Lefrancier, P.; Choay, J.; Lederer, E. Correlation of structure and adjuvant activity of N-acetyl muramyl-Lalanyl- D-isoglutamine (MDP), its derivatives and analogues. Anti-adjuvant and competition properties of stereoisomers. Biochem. Biophys. Res. Commun., 1976, 72, 339-346.
4. Fujimoto, Y.; Inamura, S.; Kawasaki, A.; Shiokawa, Z.; Shimoyama, A.; Hashimoto, T.; Kusumoto, S.; Fukase, K. Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism. J. Endotoxin Res., 2007, 13, 189-196. (Pubitemid 47471321)
5. Adam, A.; Lederer, E. Muramyl Peptides: Immunomodulators, Sleep Factors and Vitamins. Med. Res. Rev., 1984, 4, 111-152. (Pubitemid 14149766)
6. Adam, A.; Lederer, E. Muramylpeptides as immunomodulators. ISI Atlas Sci., 1988, 1, 205-214.
7. Bahr, G.M.; Darcissac, E.; Bevec, D.; Dukor, P.; Chedid, L. Immunopharmacological activities and clinical development of muramyl peptides with particilar emphasis on murabutide. Int. J. Immunopharmac., 1995, 17, 117-131.
8. Baschang, G. Muramylpeptides and lipopeptides: studies towards immunostimulants. Tetrahedron, 1989, 45, 6331-6360. (Pubitemid 19268241)
9. Dzierzbicka, K.; Kočodziejczyk, A.M. Muramyl peptides - synthesis and biological activity. Pol. J. Chem., 2003, 77, 373-395. (Pubitemid 36539272)
10. Girardin, S.E.; Travassos, L H.; Herve, M.; Blanot, D.; Boneca, I.G.; Philpott, D.J.; Sansonetti, P.J.; Mengin-Lecreulx, D. Peptidoglycan molecular requirements allowing detection by Nod1 and Nod2. J. Biol. Chem., 2003, 278, 41702-41708. (Pubitemid 37310428)
11. Traub, S.; von Aulock, S.; Hartung, T.; Hermann, C. MDP and other muropeptides - direct and synergistic effects on the immune system. J. Endotoxin Res., 2006, 12, 69-85. (Pubitemid 47470157)
12. Azuma, I.; Seya, T. Development of immunoadjuvants for immunotherapy of cancer. Int. Immunopharmacol., 2001, 1, 1249-1259. (Pubitemid 32522979)
13. Takada, H.; Yokoyama, S.; Yang, S. Enhancement of endotoxin activity by muramyldipeptide. J. Endotoxin. Res., 2002, 8, 337-342. (Pubitemid 35460668)
14. Nardin, A.; Lefebvre, M.L.; Labroquere, K.; Faure, O.; Abastado, J.P. Liposomal muramyl tripeptide phosphatidylethanolamine: Targeting and activating macrophages for adjuvant treatment of osteosarcoma. Curr. Cancer Drug Tar., 2006, 6, 123-133.
15. Bahr, G.M.; De La Tribomiere, X.; Darcissac, E.; Ajana, F.; Bocket L.; Sissako, D.; Yazdanpanah, Y.; Dewulf, J.; Amiel, C.; Mouton, Y. Clinical and immunological effects of a 6 week immunotherapy cycle with murabutide in HIV-1 patients with unsuccessful long-term antiretroviral treatment. J. Antimicrob. Chemother., 2003, 51, 1377-1388. (Pubitemid 36748926)
16. Darcissac, E.; Vidal, V.; Guuillaune, M.; Thebault, J.J.; Bahr, G.M. Clinical tolerance and profile of cytokine induction in healthy volunteers following the simultaneous administration of IFN-alpha and the synthetic immunomodulator murabutide. J. Interferon. Cytokine Res., 2001, 21, 655-661. (Pubitemid 32955695)
17. Dzierzbicka, K.; Trzonkowski, P.; Sewerynek, P.; Kočodziejczyk, A.M.; Myśliwski, A. Synthesis and biological activity of tuftsin, its analogue and conjugates containing muramyl dipeptides or nor-muramyl dipeptides. J. Pept. Sci., 2005, 11, 123-135. (Pubitemid 40347544)
18. Klimp, A.H.; de Vries, E.G.E.; Shcerphof, G.L.; Daemen, T. A potential role of macrophage activation in the treatment of cancer. Crit. Rev. Oncol./Hemat., 2002, 44, 143-161. (Pubitemid 36159043)
19. Ekman, A.K.; Cardell, L.O. The expression and function of Nod-like receptors in neutrophils. Immunology, 2010, 130(1), 55-63.
20. Duan, W.; Mehta, A.K.; Magalhaes, J.G.; Ziegler, S.F.; Dong, C.; Philpott, D.J.; Croft, M. Innate signals from Nod2 block respiratory tolerance and program T(H)2-driven allergic inflammation. J. Allergy Clin. Immunol., 2010, 126(6), 1284-1293.
21. van der Meer, J.H.; Netea, M.G.; Dinarello, C.A. Modulation of muramyl dipeptide stimulation of cytokine production by blood components. Clin. Exp. Immunol., 2009, 156(3), 428-433.
22. Sevcík, J.; Masek, K. The interaction of immunomodulatory muramyl dipeptide with peripheral 5-HT receptors: overview of the current state. Int. J. Immunopharmacol., 1999, 21(3), 227-232. (Pubitemid 29142444)
23. Marina-Garcia, N.; Franchi, L.; Kim, Y.G.; Hu, Y.J.; Smith, D.E.; Boons, G.J.; Nunez, G. Clathrin- and dynamin-dependent endocytic pathway regulates muramyl dipeptide internalization and NOD2 activation. J. Immunol., 2009, 182, 4321-4327.
24. Franchi, L.; Warner, N.; Viani, K.; Nuñez, G. Function of Nod-like receptors in microbial recognition and host defense. Immunol. Rev., 2009, 227(1), 106-128.
25. Cottagnoud, P.; Gerber, C.M.; Majcherczyk, P.A.; Acosta, F.; Cottagnoud, M.; Neftel, K.; Moreillon, P.; Täuber, M.G. The stereochemistry of the amino acid side chain influences the inflammatory potential of muramyl dipeptide in experimental meningitis. Infect. Immun., 2003, 71(6), 3663-3666. (Pubitemid 36637602)
26. Traub, S.; Kubasch, N.; Morath, S.; Kresse, M.; Hartung, T.; Schmidt, R.R.; Hermann, C. Structural requirements of synthetic muropeptides to synergize with lipopolysaccharide in cytokine induction. J. Biol. Chem., 2004, 279, 8694-8700. (Pubitemid 38295924)
27. Strober, W.; Kitani, A.; Fuss, I.; Asano, N.; Watanabe, T. The molecular basis of NOD2 susceptibility mutations in Crohn's disease. Mucosal Immunol., 2008, 1S1, 5-9.
28. Kanneganti, T.D. Central roles of NLRs and inflammasomes in viral infection. Nat. Rev. Immunol., 2010, 10(10), 688-698.
29. Uehori, J.; Fukase, K.; Akazawa, T.; Uematsu, S.; Akira, S.; Funami, K.; Shingai, M.; Matsumoto, M.; Czuma, I.; Toyoshima , K.; Kusumoto, S.; Seya, T. Dendritic cell maturation induced by muramyl dipeptide (MDP) derivatives: Monoacylated MDP confers TLR2/TLR4 activation. J. Immunol., 2005, 174, 7096-7103. (Pubitemid 40705675)
30. Uehara, A.; Yang, S.; Fujimoto, Y.; Fukase, K.; Kusumoto, S; Shibata, K.; Sugawara, S.; Takeda, H. Muramyldipeptide and diaminopimelic acidcontaining desmuramylpeptides in combination with chemically synthesized Toll-like receptor agonists synergistically induced production of interleukin- 8 in a NOD2- and NOD1-dependent manner, respectively, in human monocytic cells in culture. Cell. Microbiology, 2005, 7, 53-61.
31. Kawasaki, A,; Karasudani, Y.; Otsuka, Y.; Hasegawa, M.; Inohara, N.; Fujimoto, Y.; Fukase, K. Synthesis of diaminopimelic acid containing peptidoglycan fragments and Tracheal Cytotoxin (TCT) and investigation of their biological functions. Chem. Eur. J., 2008, 14, 10318-10330.
32. Uehara, A.; Fujimoto, Y.; Kawasaki, A.; Kusumoto, S; Fukase, K.; Takada, H. Meso- diaminopimelic acid and meso-lanthionine, amino acids specific to bacterial peptidoglycans, activate human epithelial cells through NOD1. J. Immunol., 2006, 177, 1796-1804. (Pubitemid 44092517)
33. Windheim, M.; Lang, C.; Peggie, M.; Plater, L.A.; Cohen, P. Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide. Biochem. J., 2007, 404, 179-190. (Pubitemid 46849589)
34. Davey, M.P.; Martin, T.M.; Planck, S.R.; Lee, J.; Zamora, D.; Rosenbaum, J.T. Human endothelial cells express NOD2/CRD15 and increase IL-6 secretion in response to muramyl dipeptide. Microvascular Res., 2006, 71, 103-107.
35. Sladek, Z.; Rysanek, D. Expression of macrophage CD14 receptor in the course of experimental inflammatory responses induced by lipopolysaccharide and muramyl dipeptide. Vet. Med., 2008, 53, 347-357.
36. Sladek, Z.; Rysanek, D. Expression of macrophage CD44 receptor in the course of experimental inflammatory response of bovine mammary gland induced by lipopolysaccharide and muramyl dipeptide. Res. Vet. Sci., 2009, 86, 235-240.
37. Watanabe, T.; Asano, N.; Murray, P.J.; Ozato, K.; Tailor, P.; Fuss, I.J.; Kitani, A.; Strober, W. Muramyl dipeptide activation of nucleotide-binding oligomerization domain 2 protects mice from experimental colitis. J. Clin. Invest., 2008, 118, 545-559. (Pubitemid 351206545)
38. Natsuka, M.; Uehara, A.; Yang, S.; Echigo, S.; Takada, H. A polymer-type water-soluble peptidoglycan exhibited both Toll-like receptor 2-and NOD2- agonistic activities, resulting in synergistic activation of human monocytic cells. Innate Immunity, 2008, 14, 298-308.
39. Kim, H.J.; Yang, J.S.; Woo, S.S.; Kim, S.K.; Yun, C.H.; Kim, K.K.; Han, S.H. Lipoteichoic acid and muramyl dipeptide synergistically induce maturation of human dendritic cells and concurrent expression of proinflammatory cytokinez. J. Leukoc. Biol., 2007, 81, 983-989.
40. Turánek, J.; Ledvina, M.; Kašná, A,; Vacek, A.; Hŕibalová, V.; Krejči, J.; Miller, A.D. Liposomal preparations of muramyl glycopeptides as immunomodulators and adjuvants. Vaccine, 2006, 24S2, S2/90-S2/91.
41. Yang, H.Z.; Xu, S.; Liao, X.Y.; Zhang, S.D.; Liang, Z.L.; Liu, B.H.; Bai, J.Y.; Jiang, C.; Ding, J.; Cheng, G.F.; Liu, G. A novel immunostimulator, N- 2-[(alpha-O-benzyl-N- (acetylmuramyl)-L-alanyl-D-isoglutaminyl]-N-6- trans-(m-nitrocinnamoyl)-L-lysine, and its adjuvancy on the hepatitis B surface antygen. J. Med. Chem., 2005, 48, 5112-5122. (Pubitemid 41113899)
42. Jain, V.; Vyas, S.P.; Kohli, D.V. Well-defined and potent liposomal hepatitis B vaccines adjuvanted with lipophilic MDP derivatives. Nanomedicine- Nanotechnology Biology and Medicine, 2009, 5, 334-344.
43. Szilágyi, L.; Pristovšek, P. Structural aspects of peptides with immunomodulating activity. Mini-Rev. Med. Chem., 2007, 7, 861-870. (Pubitemid 47304948)
44. Chattree, V.; Khanna, N.; Bisht, V.; Rao, D.N. Liposomal delivery of Mycobacterium leprae antigen(s) with murabutide and Trat peptide inhibits Fas-mediated apoptosis of peripheral blood mononuclear cells derived from leprosy patients. Indian J. Biochem. Biophys., 2007, 44, 386-393. (Pubitemid 351481357)
45. Wolfert, M.A.; Murray, T.F.; Boons, G.J.; Moore, J.N. The origin of the synergistic effect of muramyl dipeptide with endotoxin and peptidoglycan. J. Biol. Chem., 2002, 277, 39179-39186. (Pubitemid 35190886)
46. Girardin, S.E.; Boneca, I.G.; Viala, J.; Chamaillard, M.; Labigne, A.; Thomas, G.; Philpott, D.; Samsonetti, P.J. Nod2 is a general sensor of peptidoglycan through muramyl dipeptide (MDP) detection. J. Biol. Chem., 2003, 278, 8869-8872. (Pubitemid 36800360)
47. Inohara, N.; Ogura, Y.; Fontalba, A.; Gutierrez, O,; Pons, F.; Crespo, J.; Fukase, K.; Inamura, S.; Kusumoto, S.; Hashimoto, M.; Foster, S.j.; Moran, A.P. Fernandez-Luna, J.L.; Nunez, G. Host recognition of bacterial muramyl dipeptide mediated through NOD2. J. Biol. Chem., 2003, 278, 5509-5512. (Pubitemid 36800790)
48. Wardowska, A.; Dzierzbicka, K.; Szaryńska, M.; Da̧browska-Szponar, M.; Wiśniewska, K.; Myśliwski, A.; Trzonkowski, P. Analogues of muramyl dipeptide (MDP) and tuftsin limit infection and inflammation in murine model of sepsis. Vaccine, 2009, 27, 369-374.
49. Bergman, P.J. Cancer Immunotherapy. Topics in Companion Animal Medicine, 2009, 24, 130-136.
50. Kleinerman, E.S.; Jia, S.F.; Griffin, J.; Seibel, N.I.; Benjamin, R.S.; Jaffe, N. Phase-II study of liposomal muramyl tripeptide in osteosarcoma - the cytokine cascade and monocyte activation following administration. J. Clin. Oncol., 1992, 10, 1310-1316.
51. Asano, T.; Kleinerman, E.S. Liposome-encapsulated MTP-PE - a novel biologic agent for cancer-therapy. J. Immunother., 1993, 14, 286-292. (Pubitemid 23322747)
52. Dzierzbicka, K.; Gozdowska, M.; Kołodziejczyk, A.M. L-MTP-PE - a potential drug for cancer therapy. Post. Hig. Med. Dočw., 1997, 51, 227-236.
53. Anon, Mifamurtide - CGP 19835, CGP 19835A, L-MTP-PE, liposomal MTP-PE, MLV 19835A, MTP-PE, muramyltripeptide phosphatidylethanolamine. Drugs in R@D, 2008, 9, 131-135.
54. Meyers, P.A. Muramyl tripeptide (mifamurtide) for the treatment of osteosarcoma. Expert Rev. Anticancer Ther., 2009, 9, 1035-1049.
55. Mori, K.; Ando, K.; Heymann, D. Liposomal muramyl tripeptide phosphatidyl ethanolamine: a safe and effective agent against osteosarcoma pulmonary metastases. Expert Rev. Anticancer Ther., 2008, 8, 151-159. (Pubitemid 351385905)
56. Dvoroznakova, E.; Porubcova, J.; Snabel, V.; Fedorocko, P. Imunomodulative effect of liposomized muramyltripeptide phosphatidylethanolamine (L-MTP-PE) on mice with alveolar echinococcosis and treated with albendazole. Parasitol. Res., 2008, 103, 919-929.
57. Tamura, M.; Yoo, Y.C.; Yoshimatsu, K.; Yoshida, R.; Oka, T.; Ohkuma, K.; Arikawa, J. Azuma, I. Effects of muramyl dipeptide derivatives as adjuvants on the induction of antibody-response to recombinant hepatitis-B surfaceantigen. Vaccine, 1995, 13, 77-82.
58. Fukushima, A.; Yoo, Y.C.; Yoshimatsu, K.; Matsuzawa, K.; Tamura, M.; Tonooka, S.; Taniguchi, K.; Urasawa, S.; Arikawa, J.; Azuma, I. Effect of MDP-Lys(L18) as a mucosal immunoadjuvant on protection of mucosal infections by Sendai virus and rotavirus. Vaccine, 1996, 14, 485-491. (Pubitemid 26173750)
59. Petrova, E.E.; Valyakina, T.I.; Simonova, M.A.; Komaleva, R.L.; Khaidukov, S.V.; Makarov, E.A.; Blokhin D.Y.; Ivanov, P.K.; Andronova, T.M.; Nesmeyanov, V.A. Muramyl peptides augment cytotoxic effect of tumor necrosis factor-alpha in combination with cytotoxic drugs on tumor cells. Int. Immunopharmacol., 2006, 6, 1377-1386. (Pubitemid 44038679)
60. Petrova, E.E.; Valyakina, T.I.; Komaleva, R.L.; Simonova, M.A.; Nesmeyanov, V.A. Glucosaminylmuramyl dipeptide potentiates the effects of tumor necrosis factor-alpha and cisplatin on transformed cells in vitro. Bull. Exp. Biol. Med., 2007, 143, 251-254. (Pubitemid 47225385)
61. Csuk, R.; Göthe, G. Synthesis of cyclopropanoid analogues of N-acylmuramyldipeptide as potential immunostimulants. Tetrahedron, 2004, 60, 2201-2211. (Pubitemid 38224573)
62. Csuk, R.; Göthe, G. Synthesis of cyclopropanoid 2-epi- muramyldipeptide analogues as potential immunostimulants. Tetrahedron, 2004, 60, 2191-2199. (Pubitemid 38224572)
63. Zemlyakov, A.E.; Tsikalova, V.N.; Tsikalov, V.V.; Chirva, V.Y.; Mulik, E.L.; Kalyuzhin, O.V. Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-Disoglutamine. Russ. J. Bioorg. Chem., 2006, 32, 382-388. (Pubitemid 44048641)
64. Zemlyakov, A.E.; Tsikalova, V.N.; Tsikalov, V.V.; Chirva, V.Y.; Mulik, E.L.; Kuzovlev F.N.; Kalyuzhin, O.V.; Kiselevsky, M.V. Dialkylmethyl beta-glycosides of N-acetyl- muramyl-L-Alanyl-D-isoglutamine: Synthesis and protective antiinfection and cytotoxic activities. Russ. J. Bioorg. Chem., 2008, 34, 103-109. (Pubitemid 351650949)
65. Zemlyakov, A.E.; Tsikalova, V.N.; Azizova, L.R.; Chirva, V.Y.; Mulik, E.L.; Shkalev, M.V.; Kalyuzhin, O.V.; Kiselevsky, M.V. Synthesis and biological activity of aryl S-beta- glycosides of 1-thio-N-acetylmuramyl-Lalanyl- D-isoglutamine. Russ. J. Bioorg. Chem., 2008, 34, 223-229. (Pubitemid 351534244)
66. Roychowdhury, A.; Wolfert, M.A.; Boons, G-J. Synthesis and proinflammatory properties of muramyl tripeptides containing lysine and diaminopimelic acid moieties. ChemBioChem, 2005, 6, 2088-2097. (Pubitemid 41598185)
67. Liu, G.; Zhang, S.D.; Xin, S.Q.; Ding, Z.K. Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin metod. Bioorg. Med. Chem. Lett., 2000, 10, 1361-1363. (Pubitemid 30391969)
68. Zhang, S.D.; Liu, G.; Xin, S.Q.; Wu, P. Design and synthesis of muramyl dipeptide cyclic analogue. Chin. Chem. Lett., 2002, 13, 17-18.
69. Zhang, S.D.; Liu, G.; Xin, S.Q.; Wu, P., Zhang, I. "Meshed-Bag Gathered- Bunch" method for solid-phase synthesis of small molecular diverse compounds. J. Comb. Chem., 2002, 4, 131-137.
70. Babič, A.; Pečar, S. Synthesis of protected hydroxyethylamine transitionstate analogs of N-Ac-muramyl-L-alanine. Synthetic Commun., 2008, 38, 3052-3061.
71. Li, X.; Yu, J.; Xu, S.; Wang, N.; Yang, H.; Yan, Z.; Cheng, G.; Liu, G. Chemical conjugation of muramyl dipeptide and paclitaxel to explore the combination of immunotherapy and chemotherapy for cancer. Glycoconj. J., 2008, 25, 415-425.
72. Dzierzbicka, K.; Kołodziejczyk, A.M. Inhibitors of microtubule in cancer therapy. Wiad. Chem., 2006, 60, 345-364.
73. Laman, A.G.; Shepelyakovskaya, A.O.; Berezin, I.A.; Boziev, K.M.; Rodionov, I.L.; Chulina, I.A.; Malakhova, G.V.; Brovko, F.A.; Murashev, A.N.; Korpela, T.K.; Nesmeyanov, V.A. Identitication of pentadecapeptide mimicking muramyl peptide. Vaccine, 2007, 25, 2900-2906. (Pubitemid 46420610)
74. Cai, Y.; Ling, Ch-Ch.; Bundle, D.R. Concise and Efficient Synthesis of 2- Acetamido-2- deoxy-beta-D-hexopyranosides of Diverse Aminosugars from 2-Acetamido-2-deoxy-beta-D-glucose. J. Org. Chem., 2009, 74, 580-589.
75. Hesek, D.; Lee, M.; Hang, W.; Noll B.C.; Mobashery, S. Total Synthesis of N-Acetyl- glucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli. J. Am. Chem. Soc., 2009, 131, 5187-5193.
76. Dzierzbicka, K.; 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., 2001, 44, 3606-3615. (Pubitemid 33026668)
77. Flowers, H.M.; Jeanloz, R.W. The synthesis of 2-acetamido-3-O-(D-1- carboxy-ethyl)-2-deoxy-α-D-glucose (N-acetyl-muramic acid) and of benzyl glycoside derivatives of 2-amino-3-O-(D-1-carboxy-ethyl)-2-deoxy-Dglucose (muramic acid). J. Org. Chem., 1963, 28, 2983-2986.
78. Dzierzbicka, K.; Kołodziejczyk, A.M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridine/acridone derivatives. J. Med. Chem., 2003, 46, 183-189. (Pubitemid 36043798)
79. 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., 2003, 46, 978-986. (Pubitemid 36423144)
80. Kołodziejczyk, A.M.; Kołodziejczyk, A.S.; Stoev, S. New convenient synthesis of immunostimulating peptides containing meso-diaminopimelic acid - synthesis of FK-565 and FK-156. Int. J. Pept. Protein Res., 1992, 39, 382-387.
81. Trzonkowski, P.; Dzierzbicka, K.; Bociewicz, J.; Szmit, E.; Myśliwski, A. Biological activity of conjugates of muramyl dipeptides with batracyclin derivatives. Int. Immunopharmacol., 2005, 5, 241-251. (Pubitemid 40126350)
82. Dzierzbicka, K. Synthesis of conjugates of muramyl dipeptide and normuramyl dipeptide with retro-tuftsin (Arg-Pro-Lys-ThrOMe) as potential immunostimulants. Pol. J. Chem., 2004, 78, 409-416. (Pubitemid 38407463)
83. Dzierzbicka, K. Synthesis of new conjugates of MDP and nor-MDP with retro-tuftsin derivatives as potential immunomodulators. Pol. J. Chem., 2008, 82, 1431-1439.
84. Wardowska, A.; Dzierzbicka, K.; Trzonkowski, P.; Myśliwski, A. Immunomodulatory properties of new conjugates of muramyl dipeptide and nor-muramyl dipeptide with retro-tuftsin (Arg-Pro-Lys-Thr-OMe). Int. Immunopharmacol., 2006, 6, 1560-1568. (Pubitemid 44216198)