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74817-61-1-Murabutide Murabutide

Murabutide

For research use only. Not for therapeutic Use.

  • CAT Number: I032887
  • CAS Number: 74817-61-1
  • Molecular Formula: C23H40N4O11
  • Molecular Weight: 548.59
  • Purity: 98%
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Related Small Molecules: OXFBD02     INDY     NS3694    

Murabutide (Cat.No:I032887) is a synthetic immunomodulatory peptide derived from bacterial peptidoglycan. It acts as an immune stimulant by activating toll-like receptor 2 (TLR2) and enhancing the production of cytokines and chemokines. Murabutide has shown potential in immunotherapy and as an adjuvant in vaccines, with applications in infectious diseases and cancer treatment.


Catalog Number I032887
CAS Number 74817-61-1
Synonyms

Murabutide

Molecular Formula C23H40N4O11
Purity 98%
Target HIV
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 2-Acetamido-3-O-((R)-1-(((S)-1-(((R)-3-carbamoyl-1-carboxypropyl)carbamoyl)ethyl)carbamoyl)ethyl)-2-deoxy-D-glucopyranose, butyl ester
InChI InChI=1S/C23H40N4O11/c1-5-6-9-36-22(34)14(7-8-16(24)30)27-20(32)11(2)25-21(33)12(3)37-19-17(26-13(4)29)23(35)38-15(10-28)18(19)31/h11-12,14-15,17-19,23,28,31,35H,5-10H2,1-4H3,(H2,24,30)(H,25,33)(H,26,29)(H,27,32)/t11-,12+,14+,15+,17+,18+,19+,23?/m0/s1
InChIKey ZDSXRJABOCTJTD-HUYBTDLASA-N
SMILES OC1[C@H](NC(C)=O)[C@H]([C@@H]([C@@H](CO)O1)O)O[C@@H](C(N[C@H](C(N[C@@H](C(OCCCC)=O)CCC(N)=O)=O)C)=O)C
Reference

1: Jakopin Ž. Murabutide revisited: a review of its pleiotropic biological effects. Curr Med Chem. 2013;20(16):2068-79. doi: 10.2174/0929867311320160002. PMID: 23531213.
2: Liu L, Qu H, Qin H, Yang Y, Liao Z, Cui J, Gao F, Cai J. NOD2 agonist murabutide alleviates radiation-induced injury through DNA damage response pathway mediated by ATR. J Cell Physiol. 2019 Nov;234(11):21294-21306. doi: 10.1002/jcp.28734. Epub 2019 May 3. PMID: 31054162.
3: Kantipakala R, Bonam SR, Vemireddy S, Miryala S, Halmuthur M SK. Squalane- based emulsion vaccine delivery system: composition with murabutide activate Th1 response. Pharm Dev Technol. 2019 Mar;24(3):269-275. doi: 10.1080/10837450.2018.1469150. Epub 2018 Jul 4. PMID: 29688119.
4: Audibert FM, Przewlocki G, Leclerc CD, Jolivet ME, Gras-Masse HS, Tartar AL, Chedid LA. Enhancement by murabutide of the immune response to natural and synthetic hepatitis B surface antigens. Infect Immun. 1984 Jul;45(1):261-6. PMID: 6735468; PMCID: PMC263310.
5: Vidal V, Dewulf J, Bahr GM. Enhanced maturation and functional capacity of monocyte-derived immature dendritic cells by the synthetic immunomodulator Murabutide. Immunology. 2001 Aug;103(4):479-87. doi: 10.1046/j.1365-2567.2001.01269.x. PMID: 11529939; PMCID: PMC1783259.
6: Bahr GM, De La Tribonniere X, Darcissac E, Ajana F, Bocket L, Sissoko 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 Jun;51(6):1377-88. doi: 10.1093/jac/dkg244. Epub 2003 Apr 25. PMID: 12716777.
7: Amiel C, De La Tribonnière X, Vidal V, Darcissac E, Mouton Y, Bahr GM. Clinical tolerance and immunologic effects after single or repeated administrations of the synthetic immunomodulator murabutide in HIV-1-infected patients. J Acquir Immune Defic Syndr. 2002 Jul 1;30(3):294-305. doi: 10.1097/00126334-200207010-00005. PMID: 12131566.
8: Truong MJ, Delsart V, Bahr GM. Differentially expressed genes in HIV-1-infected macrophages following treatment with the virus-suppressive immunomodulator murabutide. Virus Res. 2004 Jan;99(1):25-33. doi: 10.1016/j.virusres.2003.09.011. PMID: 14687943.
9: Feinen B, Petrovsky N, Verma A, Merkel TJ. Advax-adjuvanted recombinant protective antigen provides protection against inhalational anthrax that is further enhanced by addition of murabutide adjuvant. Clin Vaccine Immunol. 2014 Apr;21(4):580-6. doi: 10.1128/CVI.00019-14. Epub 2014 Feb 19. PMID: 24554695; PMCID: PMC3993118.
10: Darcissac EC, Truong MJ, Dewulf J, Mouton Y, Capron A, Bahr GM. The synthetic immunomodulator murabutide controls human immunodeficiency virus type 1 replication at multiple levels in macrophages and dendritic cells. J Virol. 2000 Sep;74(17):7794-802. doi: 10.1128/jvi.74.17.7794-7802.2000. PMID: 10933686; PMCID: PMC112309.
11: Jackson EM, Herbst-Kralovetz MM. Intranasal vaccination with murabutide enhances humoral and mucosal immune responses to a virus-like particle vaccine. PLoS One. 2012;7(7):e41529. doi: 10.1371/journal.pone.0041529. Epub 2012 Jul 25. PMID: 22855691; PMCID: PMC3405106.
12: Bahr GM. Non-specific immunotherapy of HIV-1 infection: potential use of the synthetic immunodulator murabutide. J Antimicrob Chemother. 2003 Jan;51(1):5-8. doi: 10.1093/jac/dkg063. PMID: 12493780.
13: Bahr GM, Darcissac E, Pouillart PR, Chedid LA. 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. 1996 Feb;16(2):169-78. doi: 10.1089/jir.1996.16.169. PMID: 8742370.
14: Sridevi K, Khanna N, Chattree V, Pal PC, Haq W, Rao DN. Reversal of T cell anergy in leprosy patients: in vitro presentation with Mycobacterium leprae antigens using murabutide and Trat peptide in liposomal delivery. Int Immunopharmacol. 2003 Nov;3(12):1589-600. doi: 10.1016/S1567-5769(03)00181-4. PMID: 14555284.
15: De La Tribonniere X, Mouton Y, Vidal V, Darcissac E, Sissoko D, Fontier C, Douadi Y, Dewulf Jl, Amiel C, Bahr GM. A phase I study of a six-week cycle of immunotherapy with Murabutide in HIV-1 patients naive to antiretrovirals. Med Sci Monit. 2003 Jun;9(6):PI43-50. PMID: 12824957.
16: Darcissac EC, Bahr GM, Pouillart PR, Riveau GJ, Parant MA. Selective potentiation of cytokine expression in human whole blood by murabutide, a muramyl dipeptide analogue. Cytokine. 1996 Aug;8(8):658-66. doi: 10.1006/cyto.1996.0088. PMID: 8894442.
17: Vidal VF, Castéran N, Riendeau CJ, Kornfeld H, Darcissac EC, Capron A, Bahr GM. Macrophage stimulation with Murabutide, an HIV-suppressive muramyl peptide derivative, selectively activates extracellular signal-regulated kinases 1 and 2, C/EBPbeta and STAT1: role of CD14 and Toll-like receptors 2 and 4. Eur J Immunol. 2001 Jul;31(7):1962-71. doi: 10.1002/1521-4141(200107)31:7<1962::aid- immu1962>3.0.co;2-v. PMID: 11449348.
18: Chattree V, Khanna N, Bisht V, Rao DN. 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 Oct;44(5):386-93. PMID: 18341215.
19: Audibert F, Przewlocki G, Lefrancier P, Choay J, Chedid L. Renforcement de l’activité d’un vaccin contre l’hépatite virale de type B par association avec le murabutide [Enhancement of the activity of hepatitis B virus vaccine by association with murabutide]. C R Seances Acad Sci III. 1982 Nov 22;295(10):611-4. French. PMID: 6218866.
20: Goasduff T, Darcissac EC, Vidal V, Capron A, Bahr GM. The transcriptional response of human macrophages to murabutide reflects a spectrum of biological effects for the synthetic immunomodulator. Clin Exp Immunol. 2002 Jun;128(3):474-82. doi: 10.1046/j.1365-2249.2002.01872.x. PMID: 12067302; PMCID: PMC1906249.

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