Bimosiamose
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MedKoo CAT#: 329446

CAS#: 187269-40-5 (free acid)

Description: Bimosiamose, also known as TBC-1269, is a L/E/P-selectin antagonist potentially for the treatment of asthma, chronic obstructive pulmonary. Bimosiamose attenuates airway inflammation in COPD. Bimosiamose, an inhaled small-molecule pan-selectin antagonist, attenuates late asthmatic reactions following allergen challenge in mild asthmatics.

Chemical Structure

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Bimosiamose
CAS# 187269-40-5 (free acid)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329446
Name: Bimosiamose
CAS#: 187269-40-5 (free acid)
Chemical Formula: C46H54O16
Exact Mass: 862.34
Molecular Weight: 862.922
Elemental Analysis: C, 64.03; H, 6.31; O, 29.66

Price and Availability

Size Price Availability Quantity
2mg USD 90 Ready to ship
5mg USD 190 Ready to ship
10mg USD 350 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
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Related CAS #: 187269-40-5 (free acid)   187269-60-9 (disodium)  

Synonym: Bimosiamose; TBC-1269; TBC 1269; TBC1269.

IUPAC/Chemical Name: 2,2'-(hexane-1,6-diylbis(6'-(((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-[1,1'-biphenyl]-3',3-diyl))diacetic acid

InChi Key: RYWCQJDEHXJHRI-XJMXIVSISA-N

InChi Code: InChI=1S/C46H54O16/c47-23-35-39(53)41(55)43(57)45(61-35)59-33-15-13-25(19-31(33)29-11-5-9-27(17-29)21-37(49)50)7-3-1-2-4-8-26-14-16-34(60-46-44(58)42(56)40(54)36(24-48)62-46)32(20-26)30-12-6-10-28(18-30)22-38(51)52/h5-6,9-20,35-36,39-48,53-58H,1-4,7-8,21-24H2,(H,49,50)(H,51,52)/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+/m1/s1

SMILES Code: O[C@@H]1[C@@H](OC2=C(C3=CC=CC(CC(O)=O)=C3)C=C(CCCCCCC4=CC(C5=CC=CC(CC(O)=O)=C5)=C(O[C@@H]6[C@H]([C@H]([C@@H]([C@@H](CO)O6)O)O)O)C=C4)C=C2)O[C@H](CO)[C@@H](O)[C@@H]1O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# CAS#187269-60-9 (Bimosiamose disodium) CAS#187269-40-5 (Bimosiamose free)

Biological target: Bimosiamose (TBC-1269) is a nonoligosaccharide pan-selectin antagonist with IC50s of 88 μM, 20 μM, and 86 μM for E-selectin, P-selectin, and L-selectin, respectively.
In vitro activity: TBC1269, which acts as a pan-selectin antagonist, resulted in the inhibition of the intestinal epithelial migration of HL-60–differentiated eosinophils. The effect was dose dependent, and complete inhibition of migration was seen at 10 mg/mL concentration (Fig. 1). Therefore, the migration of HL-60–differentiated eosinophils across intestinal epithelial migration seems to be dependent on selectins and/or their ligands. The individual selectins/ligands then were investigated as potential players in the process of migration as described below. Reference: Pediatr Res. 2005 Oct;58(4):644-7. https://www.nature.com/articles/pr2005717
In vivo activity: Consistent with previous studies in the pig model, the major inflammatory cell population detected by immunohistochemical long term studies after ischemia was CD4+ T lymphocytes. No infiltrating cells were detected in Cont and Unif (data not shown). In contrast, the number of CD4+ increased between weeks 1 and 2 after reperfusion in WI 45 and particularly WI 60 (Figure 4a). After week 2, CD4+ cells plateaued up to 16 weeks following reperfusion in groups WI 45 and WI 60. In WI 60 and WI 45 groups, monocyte/macrophage increased between weeks 1 and 2 and slightly decreased between weeks 2 and 4, then plateaued between weeks 4 and 16 (Figure 4b). Monocyte/macrophage number was significantly increased in WI 60 group when compared to WI 45 group. In WI kidneys treated with TBC-1269, CD4-positive cell number was significantly reduced. Monocyte/macrophage number was also different in WI TBC 45 and WI TBC 60 when compared to WI 45 and WI 60, respectively (Figure 5a). TBC-1269 was also efficient in cold ischemia model in reducing inflammatory cells (Figure 5b). TBC-1269 reduced CD4-positive cells and macrophages during the first week, and this beneficial effect remained detectable between weeks 4 and 16. Reference: Kidney Int. 2006 May;69(10):1749-55. https://www.kidney-international.org/article/S0085-2538(15)51353-7/fulltext

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 115.89
0.1 M NaOH 25.0 28.97

Preparing Stock Solutions

The following data is based on the product molecular weight 862.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Michail S, Mezoff E, Abernathy F. Role of selectins in the intestinal epithelial migration of eosinophils. Pediatr Res. 2005 Oct;58(4):644-7. doi: 10.1203/01.PDR.0000180572.65751.F4. PMID: 16189187. 2. Jayle C, Milinkevitch S, Favreau F, Doucet C, Richer JP, Deretz S, Mauco G, Rabb H, Hauet T. Protective role of selectin ligand inhibition in a large animal model of kidney ischemia-reperfusion injury. Kidney Int. 2006 May;69(10):1749-55. doi: 10.1038/sj.ki.5000335. PMID: 16625150. 3. Armstrong PC, Hu H, Rivera J, Rigby S, Chen YC, Howden BP, Gardiner E, Peter K. Staphylococcal superantigen-like protein 5 induces thrombotic and bleeding complications in vivo: inhibition by an anti-SSL5 antibody and the glycan Bimosiamose. J Thromb Haemost. 2012 Dec;10(12):2607-9. doi: 10.1111/jth.12022. PMID: 23039170.
In vitro protocol: 1. Michail S, Mezoff E, Abernathy F. Role of selectins in the intestinal epithelial migration of eosinophils. Pediatr Res. 2005 Oct;58(4):644-7. doi: 10.1203/01.PDR.0000180572.65751.F4. PMID: 16189187.
In vivo protocol: 1. Jayle C, Milinkevitch S, Favreau F, Doucet C, Richer JP, Deretz S, Mauco G, Rabb H, Hauet T. Protective role of selectin ligand inhibition in a large animal model of kidney ischemia-reperfusion injury. Kidney Int. 2006 May;69(10):1749-55. doi: 10.1038/sj.ki.5000335. PMID: 16625150. 2. Armstrong PC, Hu H, Rivera J, Rigby S, Chen YC, Howden BP, Gardiner E, Peter K. Staphylococcal superantigen-like protein 5 induces thrombotic and bleeding complications in vivo: inhibition by an anti-SSL5 antibody and the glycan Bimosiamose. J Thromb Haemost. 2012 Dec;10(12):2607-9. doi: 10.1111/jth.12022. PMID: 23039170.

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1: Gross NJ. The COPD pipeline XXII. COPD. 2013 Jun;10(3):390-2. doi: 10.3109/15412555.2013.795422. PubMed PMID: 23713599.

2: Watz H, Bock D, Meyer M, Schierhorn K, Vollhardt K, Woischwill C, Pedersen F, Kirsten A, Beeh KM, Meyer-Sabellek W, Magnussen H, Beier J. Inhaled pan-selectin antagonist Bimosiamose attenuates airway inflammation in COPD. Pulm Pharmacol Ther. 2013 Apr;26(2):265-70. doi: 10.1016/j.pupt.2012.12.003. PubMed PMID: 23257347.

3: Armstrong PC, Hu H, Rivera J, Rigby S, Chen YC, Howden BP, Gardiner E, Peter K. Staphylococcal superantigen-like protein 5 induces thrombotic and bleeding complications in vivo: inhibition by an anti-SSL5 antibody and the glycan Bimosiamose. J Thromb Haemost. 2012 Dec;10(12):2607-9. doi: 10.1111/jth.12022. PubMed PMID: 23039170.

4: Kirsten A, Watz H, Kretschmar G, Pedersen F, Bock D, Meyer-Sabellek W, Magnussen H. Efficacy of the pan-selectin antagonist Bimosiamose on ozone-induced airway inflammation in healthy subjects--a double blind, randomized, placebo-controlled, cross-over clinical trial. Pulm Pharmacol Ther. 2011 Oct;24(5):555-8. doi: 10.1016/j.pupt.2011.04.029. PubMed PMID: 21514398.

5: Paschos KA, Canovas D, Bird NC. The engagement of selectins and their ligands in colorectal cancer liver metastases. J Cell Mol Med. 2010 Jan;14(1-2):165-74. doi: 10.1111/j.1582-4934.2009.00852.x. Review. PubMed PMID: 19627399; PubMed Central PMCID: PMC3837616.

6: Anaya-Prado R, Pérez-Gomez N, Toledo-Pereyra LH, Walsh J, Jordan J, Ward PA. Small molecule selectin inhibitor in global cerebral ischemia and controlled hemorrhagic shock. J Trauma. 2008 Sep;65(3):678-84. doi: 10.1097/TA.0b013e3181843f3a. PubMed PMID: 18784584.

7: Mayr FB, Firbas C, Leitner JM, Spiel AO, Reiter RA, Beyer D, Meyer M, Wolff G, Jilma B. Effects of the pan-selectin antagonist bimosiamose (TBC1269) in experimental human endotoxemia. Shock. 2008 Apr;29(4):475-82. PubMed PMID: 18598003.

8: Woodside DG, Vanderslice P. Cell adhesion antagonists: therapeutic potential in asthma and chronic obstructive pulmonary disease. BioDrugs. 2008;22(2):85-100. Review. PubMed PMID: 18345706.

9: Meyer M, Beyer D, Vollhardt K, Woischwill C, Jilma B, Wolff G. The pharmacokinetics of subcutaneously injected Bimosiamose disodium in healthy male volunteers. Biopharm Drug Dispos. 2007 Dec;28(9):475-84. PubMed PMID: 17876866.

10: Kranich R, Busemann AS, Bock D, Schroeter-Maas S, Beyer D, Heinemann B, Meyer M, Schierhorn K, Zahlten R, Wolff G, Aydt EM. Rational design of novel, potent small molecule pan-selectin antagonists. J Med Chem. 2007 Mar 22;50(6):1101-15. PubMed PMID: 17302397.

11: López-Neblina F, Toledo-Pereyra LH. Anti-ischemic effect of selectin blocker through modulation of tumor necrosis factor-alpha and interleukin-10. J Surg Res. 2007 Apr;138(2):275-83. PubMed PMID: 17254609.

12: Meyer M, Beeh KM, Beier J, Beyer D, Aydt E, Zahlten R, Jilma B, Wolff G. Tolerability and pharmacokinetics of inhaled bimosiamose disodium in healthy males. Br J Clin Pharmacol. 2007 Apr;63(4):451-8. PubMed PMID: 17067318; PubMed Central PMCID: PMC2203253.

13: Jayle C, Milinkevitch S, Favreau F, Doucet C, Richer JP, Deretz S, Mauco G, Rabb H, Hauet T. Protective role of selectin ligand inhibition in a large animal model of kidney ischemia-reperfusion injury. Kidney Int. 2006 May;69(10):1749-55. PubMed PMID: 16625150.

14: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Jan-Feb;28(1):31-63. PubMed PMID: 16541195.

15: Friedrich M, Bock D, Philipp S, Ludwig N, Sabat R, Wolk K, Schroeter-Maas S, Aydt E, Kang S, Dam TN, Zahlten R, Sterry W, Wolff G. Pan-selectin antagonism improves psoriasis manifestation in mice and man. Arch Dermatol Res. 2006 Feb;297(8):345-51. PubMed PMID: 16362415.

16: Meyer M, Jilma B, Zahlten R, Wolff G. Physiochemical properties, safety and pharmacokinetics of bimosiamose disodium after intravenous administration. Int J Clin Pharmacol Ther. 2005 Oct;43(10):463-71. PubMed PMID: 16240703.

17: Beeh KM, Beier J, Meyer M, Buhl R, Zahlten R, Wolff G. Bimosiamose, an inhaled small-molecule pan-selectin antagonist, attenuates late asthmatic reactions following allergen challenge in mild asthmatics: a randomized, double-blind, placebo-controlled clinical cross-over-trial. Pulm Pharmacol Ther. 2006;19(4):233-41. PubMed PMID: 16140027.

18: Beauharnois ME, Lindquist KC, Marathe D, Vanderslice P, Xia J, Matta KL, Neelamegham S. Affinity and kinetics of sialyl Lewis-X and core-2 based oligosaccharides binding to L- and P-selectin. Biochemistry. 2005 Jul 12;44(27):9507-19. PubMed PMID: 15996105.

19: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jan-Feb;27(1):49-77. PubMed PMID: 15834459.

20: Romano SJ. Selectin antagonists : therapeutic potential in asthma and COPD. Treat Respir Med. 2005;4(2):85-94. Review. PubMed PMID: 15813660.