2-Deoxy-3-O-(9-phenylnonanoyl)-2-[3(S)-(9-phenylnonanoyloxy)tetradecanamido]-4-O-sulfo-D-glucopyrano

• CAT Number: M092815
• CAS Number: 152646-95-2
• Molecular Formula: C50H78NNaO12S
• Molecular Weight: 940.21
• Purity: ≥95%
• Storage: -20°C

Ono 4007 is new synthetic low-toxicity lipid A analog which stimulates the production of tumor necrosis factor-alpha in tumor tissues, resulting in the rejection of transplanted rat hepatoma cells. Studies suggest that ONO-4007 is therapeutically useful for the treatment of TNF-alpha-sensitive tumors and tumor eradication.

Reference

1: Calvopina M, Barroso PA, Marco JD, Korenaga M, Cooper PJ, Nonaka S, Hashiguchi Y. Efficacy of vaccination with a combination of Leishmania amastigote antigens and the lipid A-analogue ONO-4007 for immunoprophylaxis and immunotherapy against Leishmania amazonensis infection in a murine model of New World cutaneous leishmaniasis. Vaccine. 2006 Jul 7;24(27-28):5645-52. Epub 2006 Mar 29. PubMed PMID: 16621179. 2: Matsushita K, Kuramitsu Y, Ohiro Y, Kobayashi I, Watanabe T, Kobayashi M, Hosokawa M. ONO-4007, a synthetic lipid A analog, induces Th1-type immune response in tumor eradication and restores nitric oxide production by peritoneal macrophages. Int J Oncol. 2003 Aug;23(2):489-93. PubMed PMID: 12851700. 3: Saito Y, Kuramitsu Y, Arai H, Kato Y, Fujimoto M, Ita M, Hayatsu Y, Shinozaki F, Nakamura K. A signaling pathway by a new synthetic lipid A analog, ONO-4007, in RAW264.7 cells. Anticancer Drugs. 2002 Nov;13(10):1069-75. PubMed PMID: 12439341. 4: Khan MA, Maruno M, Khaskhely NM, Ramzi ST, Hosokawa A, Uezato H, Landires EA, Hashiguchi Y, Nonaka S. Inhibition of intracellular proliferation of Leishmania parasites in vitro and suppression of skin lesion development in BALB/c mice by a novel lipid A analog (ONO-4007). Am J Trop Med Hyg. 2002 Aug;67(2):184-90. PubMed PMID: 12389945. 5: Iio J, Katamura K, Takeda H, Ohmura K, Yasumi T, Meguro TA, Ohshima Y, Nakahata T. Lipid A analogue, ONO-4007, inhibits IgE response and antigen-induced eosinophilic recruitment into airways in BALB/c mice. Int Arch Allergy Immunol. 2002 Mar;127(3):217-25. PubMed PMID: 11979047. 6: Satoh M, Tsurumaki K, Kagehara H, Yamazaki M. Induction of intratumoral tumor necrosis factor by a synthetic lipid A analog, ONO-4007, with less tolerance in repeated administration and its implication in potent antitumor effects with low toxicity. Cancer Immunol Immunother. 2002 Feb;50(12):653-62. Epub 2001 Dec 6. PubMed PMID: 11862417. 7: Matsumoto N, Aze Y, Akimoto A, Fujita T. ONO-4007, an antitumor lipid A analog, induces tumor necrosis factor-alpha production by human monocytes only under primed state: different effects of ONO-4007 and lipopolysaccharide on cytokine production. J Pharmacol Exp Ther. 1998 Jan;284(1):189-95. PubMed PMID: 9435177. 8: Kuramitsu Y, Nishibe M, Ohiro Y, Matsushita K, Yuan L, Obara M, Kobayashi M, Hosokawa M. A new synthetic lipid A analog, ONO-4007, stimulates the production of tumor necrosis factor-alpha in tumor tissues, resulting in the rejection of transplanted rat hepatoma cells. Anticancer Drugs. 1997 Jun;8(5):500-8. PubMed PMID: 9215614. 9: Hattori Y, Szabó C, Gross S, Thiemermann C, Vane JR. Lipid A and the lipid A analogue anti-tumour compound ONO-4007 induce nitric oxide synthase in vitro and in vivo. Eur J Pharmacol. 1995 Oct 15;291(2):83-90. PubMed PMID: 8566179. 10: Ishida H, Irie K, Suganuma T, Fujii E, Yoshioka T, Muraki T, Ogawa R. A lipid A analog ONO-4007 induces tolerance to plasma leakage in mice. Inflamm Res. 2002 Jan;51(1):38-43. PubMed PMID: 11845997. 11: Ishida H, Fujii E, Irie K, Yoshioka T, Muraki T, Ogawa R. Role of inflammatory mediators in lipid A analogue (ONO-4007)-induced vascular permeability change in mouse skin. Br J Pharmacol. 2000 Jul;130(6):1235-40. PubMed PMID: 10903960; PubMed Central PMCID: PMC1572185. 12: de Bono JS, Dalgleish AG, Carmichael J, Diffley J, Lofts FJ, Fyffe D, Ellard S, Gordon RJ, Brindley CJ, Evans TR. Phase I study of ONO-4007, a synthetic analogue of the lipid A moiety of bacterial lipopolysaccharide. Clin Cancer Res. 2000 Feb;6(2):397-405. PubMed PMID: 10690516. 13: Mizushima Y, Sassa K, Fujishita T, Oosaki R, Kobayashi M. Therapeutic effect of a new synthetic lipid A analog (ONO-4007) on a tumor implanted at different sites in rats. J Immunother. 1999 Sep;22(5):401-6. PubMed PMID: 10546155. 14: Matsumoto N, Oida H, Aze Y, Akimoto A, Fujita T. Intratumoral tumor necrosis factor induction and tumor growth suppression by ONO-4007, a low-toxicity lipid A analog. Anticancer Res. 1998 Nov-Dec;18(6A):4283-9. PubMed PMID: 9891479. 15: Matsushita K, Kobayashi M, Totsuka Y, Hosokawa M. ONO-4007 induces specific anti-tumor immunity mediated by tumor necrosis factor-alpha. Anticancer Drugs. 1998 Mar;9(3):273-82. PubMed PMID: 9625438. 16: Kuramitsu Y, Matsushita K, Ohiro Y, Obara M, Kobayashi M, Hosokawa M. Therapeutic effects of a new synthetic lipid A analog, ONO-4007, on rat hepatoma KDH-8 depend on tumor necrosis factor-sensitivity of the tumor cells. Anticancer Drugs. 1997 Oct;8(9):898-901. PubMed PMID: 9402318. 17: Kuramitsu Y, Ohiro Y, Matsushita K, Obara M, Kobayashi M, Hosokawa M. The mechanism of locally enhanced production of tumor necrosis factor-alpha in tumor tissues by the administration of a new synthetic lipid A analog, ONO-4007, in hepatoma-bearing rats. Anticancer Drugs. 1997 Oct;8(9):886-93. PubMed PMID: 9402316. 18: Matsumoto N, Aze Y, Akimoto A, Fujita T. Restoration of immune responses in tumor-bearing mice by ONO-4007, an antitumor lipid A derivative. Immunopharmacology. 1997 Apr;36(1):69-78. PubMed PMID: 9129998. 19: Ueda H, Yamazaki M. Induction of tumor necrosis factor in a murine tumor by systemic administration of a novel synthetic lipid A analogue, ONO-4007. J Immunother. 1997 Jan;20(1):65-9. PubMed PMID: 9101415. 20: Kobayashi M, Nagayasu H, Hamada J, Takeichi N, Hosokawa M. ONO-4007, a new synthetic lipid A derivative, induces differentiation of rat myelomonocytic leukemia cells in vitro and in vivo. Exp Hematol. 1994 May;22(5):454-9. PubMed PMID: 8174676.