Hexamethylene bisacetamide

• CAT Number: I011921
• CAS Number: 3073-59-4
• Molecular Formula: C10H20N2O2
• Molecular Weight: 200.282
• Purity: ≥95%
• Synonyms: Diacetyldiaminohexane; Hexamethylene bisacetamide; HMBA;;N,N/’-(hexane-1,6-diyl)diacetamide
• Target: transcription elongation factor b inhibitor
• Solubility: Soluble in DMSO
• Storage: Store at 0-8 °C
• IUPAC Name: N-(6-acetamidohexyl)acetamide
• InChI: InChI=1S/C10H20N2O2/c1-9(13)11-7-5-3-4-6-8-12-10(2)14/h3-8H2,1-2H3,(H,11,13)(H,12,14)
• InChIKey: BNQSTAOJRULKNX-UHFFFAOYSA-N
• SMILES: CC(=O)NCCCCCCNC(=O)C

Hexamethylene bisacetamide is a HEXIM1 activator that inhibits transcription elongation factor b(P-TEFb) and modulates RNA polymerase II and mRNA synthesis. It induces differentiation and apoptosis in cancer cells.

Reference

1: Nilsson LM, Green LC, Muralidharan SV, Demir D, Welin M, Bhadury J, Logan DT, Walse B, Nilsson JA. Cancer Differentiating Agent Hexamethylene Bisacetamide Inhibits BET Bromodomain Proteins. Cancer Res. 2016 Apr 15;76(8):2376-83. doi: 10.1158/0008-5472.CAN-15-2721. Epub 2016 Mar 3. PubMed PMID: 26941288.2: Smith KM, Ketchart W, Zhou X, Montano MM, Xu Y. Determination of hexamethylene bisacetamide, an antineoplastic compound, in mouse and human plasma by LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Aug 1;879(23):2206-12. doi: 10.1016/j.jchromb.2011.06.002. Epub 2011 Jun 13. PubMed PMID: 21723208; PubMed Central PMCID: PMC4068250.3: Ren X, Zhang Y, Li C, Wang H, Jiang Z, Zhang Z, Guo Q, Song G, Bi K, Jiang G. Enhancement of baicalin by hexamethylene bisacetamide on the induction of apoptosis contributes to simultaneous activation of the intrinsic and extrinsic apoptotic pathways in human leukemia cells. Oncol Rep. 2013 Nov;30(5):2071-80. doi: 10.3892/or.2013.2684. Epub 2013 Aug 21. PubMed PMID: 23970138.4: Ward FT, Kelley JA, Roth JS, Lombardo FA, Weiss RB, Leyland-Jones B, Chun HG. Phase I bioavailability and pharmacokinetic study of hexamethylene bisacetamide (NSC 95580) administered via nasogastric tube. Cancer Res. 1991 Apr 1;51(7):1803-10. PubMed PMID: 2004365.5: Parekh D, Ishizuka J, Townsend CM Jr, Haber BE, Beauchamp RD, Rajaraman S, Karp G, Hsieh J, Thompson JC. Differential effects of sodium butyrate and hexamethylene bisacetamide on growth and secretion of cultured human endocrine tumor cells. Arch Surg. 1991 Apr;126(4):467-72. PubMed PMID: 1706915.6: Naito S, Obayashi S, Sumi T, Iwai S, Nakazawa M, Ikuta K, Yura Y. Enhancement of antitumor activity of herpes simplex virus gamma(1)34.5-deficient mutant for oral squamous cell carcinoma cells by hexamethylene bisacetamide. Cancer Gene Ther. 2006 Aug;13(8):780-91. Epub 2006 Apr 28. PubMed PMID: 16645620.7: Ouchida R, Kusuhara M, Shimizu N, Hisada T, Makino Y, Morimoto C, Handa H, Ohsuzu F, Tanaka H. Suppression of NF-kappaB-dependent gene expression by a hexamethylene bisacetamide-inducible protein HEXIM1 in human vascular smooth muscle cells. Genes Cells. 2003 Feb;8(2):95-107. PubMed PMID: 12581153.8: Hassan HT, Rees JK. Effect of AML serum on normal human myeloid differentiation and hexamethylene bisacetamide-induced granulocytic differentiation of the human HL-60 promyelocytic leukaemic cell line. Folia Haematol Int Mag Klin Morphol Blutforsch. 1990;117(1):151-9. PubMed PMID: 1695170.9: Petrak J, Myslivcova D, Man P, Cmejlova J, Cmejla R, Vyoral D. Proteomic analysis of erythroid differentiation induced by hexamethylene bisacetamide in murine erythroleukemia cells. Exp Hematol. 2007 Feb;35(2):193-202. PubMed PMID: 17258068.10: Callery PS, Egorin MJ, Geelhaar LA, Nayar MS. Identification of metabolites of the cell-differentiating agent hexamethylene bisacetamide in humans. Cancer Res. 1986 Oct;46(10):4900-3. PubMed PMID: 3756851.11: Cecchinato V, Erba E, Basile A, Scarpati B, Fazi C, Brando B, Comi P, Chiaramonte R. Hexamethylene bisacetamide inhibits malignant phenotype in T-ALL cell lines. Leuk Res. 2008 May;32(5):791-7. Epub 2007 Oct 26. PubMed PMID: 17964649.12: Conley BA, Egorin MJ, Zuhowski EG, Sinibaldi VJ, Peterson DE. Salivary concentrations of hexamethylene bisacetamide (HMBA) in patients receiving 5-day continuous infusions. Cancer Chemother Pharmacol. 1988;22(1):65-8. PubMed PMID: 3396146.13: Ren X, Wen PE, Yang WH, Tang TH, Ren HQ, Zhang ZY, Zhao HT, Fan H, Qiao GJ, Jiang GH. [Molecular mechanism underlying differentiation of HL-60 cells induced by hexamethylene bisacetamide]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2008 Oct;16(5):1030-4. Chinese. PubMed PMID: 18928589.14: Kitagawa R, Takahashi Y, Takahashi M, Imazu H, Yasuda M, Sadanari H, Tanaka J. Hexamethylene bisacetamide can convert nonpermissive human cells to a permissive state for expressing the major immediate-early genes of human cytomegalovirus by up-regulating NF-kappaB activity. Virology. 2009 Jan 20;383(2):195-206. doi: 10.1016/j.virol.2008.10.028. Epub 2008 Nov 22. PubMed PMID: 19027925.15: Roth JS, Kelley JA, Chun HG, Ward FT. Simultaneous measurement of the cell-differentiating agent hexamethylene bisacetamide and its metabolites by gas chromatography. J Chromatogr. 1994 Feb 11;652(2):149-59. PubMed PMID: 8006099.16: Burris CA, de Silva S, Narrow WC, Casey AE, Lotta LT Jr, Federoff HJ, Bowers WJ. Hexamethylene bisacetamide leads to reduced helper virus-free HSV-1 amplicon expression titers via suppression of ICP0. J Gene Med. 2008 Feb;10(2):152-64. PubMed PMID: 18058952; PubMed Central PMCID: PMC2440655.17: Ogawa T, Hayashi T, Yorioka N, Kyoizumi S, Trosko JE. Hexamethylene bisacetamide protects peritoneal mesothelial cells from glucose. Kidney Int. 2001 Sep;60(3):996-1008. PubMed PMID: 11532094.18: Michaeli J, Busquets X, Orlow I, Younes A, Colomer D, Marks PA, Rifkind RA, Kolesnick RN. A rise and fall in 1,2-diacylglycerol content signal hexamethylene bisacetamide-induced erythropoiesis. J Biol Chem. 1992 Nov 25;267(33):23463-6. PubMed PMID: 1429688.19: Schroy PC 3rd, Carnright K, Winawer SJ, Friedman EA. Heterogeneous responses of human colon carcinomas to hexamethylene bisacetamide. Cancer Res. 1988 Oct 1;48(19):5487-94. PubMed PMID: 2458179.20: Dey A, Wong E, Kua N, Teo HL, Tergaonkar V, Lane D. Hexamethylene bisacetamide (HMBA) simultaneously targets AKT and MAPK pathway and represses NF kappaB activity: implications for cancer therapy. Cell Cycle. 2008 Dec;7(23):3759-67. Epub 2008 Dec 10. PubMed PMID: 19029824.