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bimosiamose , Selectin inhibitor, CAS No.187269-40-5, Selectin inhibitor

Item Number
B608090
Grouped product items
SKUSizeAvailabilityPrice Qty
B608090-5mg
5mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,334.90
B608090-25mg
25mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$2,001.90
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View related series
selectin P (CD62) Inhibitor

Basic Description

SynonymsBimosiamose | 187269-40-5 | TBC-1269 | Bimosiamose [INN] | TBC 1269 | 97B5KCW80W | CHEMBL1215923 | DTXSID8048783 | NCGC00183833-01 | 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))di
Specifications & PurityMoligand™
GradeMoligand™
Action TypeINHIBITOR
Mechanism of actionSelectin inhibitor

Product Properties

ALogP4.2

Associated Targets(Human)

SELP Tclin P-selectin (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
SELPLG Tbio P-selectin glycoprotein ligand 1 (134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SELL Tchem Leukocyte adhesion molecule-1 (145 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Sele Selectin E (1 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Selp P-selectin (7 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ovis aries (854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Luciferin 4-monooxygenase (66902 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Names and Identifiers

IUPAC Name 2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid
INCHI 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
InChi Key RYWCQJDEHXJHRI-XJMXIVSISA-N
Canonical SMILES OC[C@H]1O[C@H](Oc2ccc(cc2c2cccc(c2)CC(=O)O)CCCCCCc2ccc(c(c2)c2cccc(c2)CC(=O)O)O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)[C@H]([C@H]([C@@H]1O)O)O
Isomeric SMILES C1=CC(=CC(=C1)C2=C(C=CC(=C2)CCCCCCC3=CC(=C(C=C3)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=CC(=C5)CC(=O)O)O[C@@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)CC(=O)O
PubChem CID 9811353
Molecular Weight 862.9

Certificates

Certificate of Analysis(COA)

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Related Documents

 SDS

 Specification Sheet

References

1. Nemoto T, Burne MJ, Daniels F, O'Donnell MP, Crosson J, Berens K, Issekutz A, Kasiske BL, Keane WF, Rabb H.  (2001)  Small molecule selectin ligand inhibition improves outcome in ischemic acute renal failure..  Kidney Int,  60  (6): (2205-14).  [PMID:11737594]
2. Romano SJ, Slee DH.  (2001)  Targeting selectins for the treatment of respiratory diseases..  Curr Opin Investig Drugs,  2  (7): (907-13).  [PMID:11757789]
3. Onai Y, Suzuki J, Nishiwaki Y, Gotoh R, Berens K, Dixon R, Yoshida M, Ito H, Isobe M.  (2003)  Blockade of cell adhesion by a small molecule selectin antagonist attenuates myocardial ischemia/reperfusion injury..  Eur J Pharmacol,  481  (2-3): (217-25).  [PMID:14642789]
4. Vanderslice P, Biediger RJ, Woodside DG, Berens KL, Holland GW, Dixon RA.  (2004)  Development of cell adhesion molecule antagonists as therapeutics for asthma and COPD..  Pulm Pharmacol Ther,  17  (1): (1-10).  [PMID:14643165]
5. Hicks AE, Abbitt KB, Dodd P, Ridger VC, Hellewell PG, Norman KE.  (2005)  The anti-inflammatory effects of a selectin ligand mimetic, TBC-1269, are not a result of competitive inhibition of leukocyte rolling in vivo..  J Leukoc Biol,  77  (1): (59-66).  [PMID:15466915]
6. Toledo-Pereyra LH, Lopez-Neblina F, Reuben JS, Toledo AH, Ward PA.  (2004)  Selectin inhibition modulates Akt/MAPK signaling and chemokine expression after liver ischemia-reperfusion..  J Invest Surg,  17  (6): (303-13).  [PMID:15764497]
7. Anaya-Prado R, Pérez-Gomez N, Toledo-Pereyra LH, Walsh J, Jordan J, Ward PA.  (2008)  Small molecule selectin inhibitor in global cerebral ischemia and controlled hemorrhagic shock..  J Trauma,  65  (3): (678-84).  [PMID:18784584]
8. Calvey CR, Toledo-Pereyra LH.  (2007)  Selectin inhibitors and their proposed role in ischemia and reperfusion..  J Invest Surg,  20  (2): (71-85).  [PMID:17454392]
9. Watz H, Bock D, Meyer M, Schierhorn K, Vollhardt K, Woischwill C, Pedersen F, Kirsten A, Beeh KM, Meyer-Sabellek W et al..  (2013)  Inhaled pan-selectin antagonist Bimosiamose attenuates airway inflammation in COPD..  Pulm Pharmacol Ther,  26  (2): (265-70).  [PMID:23257347]
10. Kogan TP, Dupré B, Bui H, McAbee KL, Kassir JM, Scott IL, Hu X, Vanderslice P, Beck PJ, Dixon RA.  (1998)  Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D- mannopyranosyloxy)phenyl]hexane (TBC1269)..  J Med Chem,  41  (7): (1099-111).  [PMID:9544210]

Solution Calculators

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