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84290-27-7-Tucaresol Tucaresol

Tucaresol

For research use only. Not for therapeutic Use.

  • CAT Number: I037603
  • CAS Number: 84290-27-7
  • Molecular Formula: C15H12O5
  • Molecular Weight: 272.256
  • Purity: 98%
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Related Small Molecules: 1-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-one     BpV(HOpic)     RAGE antagonist peptide    

Tucaresol(CAT: I037603) has been investigated in clinical trials for its potential to treat HIV infections. As part of these trials, Tucaresol’s therapeutic effects and safety profile were assessed in individuals affected by HIV. These studies aimed to explore the compound’s ability to target and manage the viral infection, potentially contributing to advancements in HIV treatment strategies.


Catalog Number I037603
CAS Number 84290-27-7
Synonyms

589C; 589C80; BW 589C; BW A589C; BW-589C

Molecular Formula C15H12O5
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 4-((2-formyl-3-hydroxyphenoxy)methyl)benzoic acid
InChI InChI=1S/C15H12O5/c16-8-12-13(17)2-1-3-14(12)20-9-10-4-6-11(7-5-10)15(18)19/h1-8,17H,9H2,(H,18,19)
InChIKey XEDONBRPTABQFB-UHFFFAOYSA-N
SMILES OC(c1ccc(COc2c(C=O)c(O)ccc2)cc1)=O
Reference

1: Collins KC, Schlosburg JE, Lockner JW, Bremer PT, Ellis BA, Janda KD. Lipid tucaresol as an adjuvant for methamphetamine vaccine development. Chem Commun (Camb). 2014 Apr 21;50(31):4079-81. doi: 10.1039/c4cc00682h. PMID: 24615284; PMCID: PMC4033696.
2: Wright SE, Rewers-Felkins KA, Chowdhury NI, Ahmed J, Srivastava SK, Lockwood- Cooke PR. Tucaresol down-modulation of MUC1-stimulated human mononuclear cells. Immunol Invest. 2014;43(2):160-9. doi: 10.3109/08820139.2013.860161. Epub 2013 Dec 4. PMID: 24303799.
3: Arya R, Rolan PE, Wootton R, Posner J, Bellingham AJ. Tucaresol increases oxygen affinity and reduces haemolysis in subjects with sickle cell anaemia. Br J Haematol. 1996 Jun;93(4):817-21. doi: 10.1046/j.1365-2141.1996.d01-1744.x. PMID: 8703810.
4: Clerici M, Cogliati M, Rizzardini G, Colombo F, Fossati S, Rhodes J, Bray D, Piconi S. In vitro immunomodulatory properties of tucaresol in HIV infection. Clin Immunol. 2000 Dec;97(3):211-20. doi: 10.1006/clim.2000.4937. PMID: 11112360.
5: Gori A, Trabattoni D, Bandera A, Saresella M, Marchetti G, Gazzola L, Biasin M, Rhodes J, McDade H, Panebianco R, Galli M, Moroni M, Ferrante P, Thomas N, Franzetti F, Bray D, Clerici M. Immunomodulation induced by tucaresol in HIV infection: results of a 16 week pilot Phase I/II trial. Antivir Ther. 2004 Aug;9(4):603-14. PMID: 15456092.
6: Rolan PE, Mercer AJ, Wootton R, Posner J. Pharmacokinetics and pharmacodynamics of tucaresol, an antisickling agent, in healthy volunteers. Br J Clin Pharmacol. 1995 Apr;39(4):375-80. doi: 10.1111/j.1365-2125.1995.tb04465.x. PMID: 7640143; PMCID: PMC1365124.
7: Fernández-Tejada A, Chea EK, George C, Gardner JR, Livingston PO, Ragupathi G, Tan DS, Gin DY. Design, synthesis, and immunologic evaluation of vaccine adjuvant conjugates based on QS-21 and tucaresol. Bioorg Med Chem. 2014 Nov 1;22(21):5917-23. doi: 10.1016/j.bmc.2014.09.016. Epub 2014 Sep 17. PMID: 25284254; PMCID: PMC4410046.
8: Peck RW, Wootton R, Wiggs R, Layton G, Posner J. Effect of food and gender on the pharmacokinetics of tucaresol in healthy volunteers. Br J Clin Pharmacol. 1998 Jul;46(1):83-6. doi: 10.1046/j.1365-2125.1998.00047.x. PMID: 9690954; PMCID: PMC1873973.
9: Smith AC, Yardley V, Rhodes J, Croft SL. Activity of the novel immunomodulatory compound tucaresol against experimental visceral leishmaniasis. Antimicrob Agents Chemother. 2000 Jun;44(6):1494-8. doi: 10.1128/aac.44.6.1494-1498.2000. PMID: 10817698; PMCID: PMC89902.
10: Bulgheroni E, Bandera A, Galli M, Gori A, Rusconi S. Analysis of the env V3 sequences obtained from patients with HIV type 1 infection treated with the immune modulant agent tucaresol. AIDS Res Hum Retroviruses. 2005 Sep;21(9):815-9. doi: 10.1089/aid.2005.21.815. PMID: 16218807.
11: Rolan PE, Parker JE, Gray SJ, Weatherley BC, Ingram J, Leavens W, Wootton R, Posner J. The pharmacokinetics, tolerability and pharmacodynamics of tucaresol (589C80; 4[2-formyl-3-hydroxyphenoxymethyl] benzoic acid), a potential anti- sickling agent, following oral administration to healthy subjects. Br J Clin Pharmacol. 1993 Apr;35(4):419-25. doi: 10.1111/j.1365-2125.1993.tb04160.x. PMID: 8485022; PMCID: PMC1381554.
12: Chen H, Hall S, Heffernan B, Thompson NT, Rogers MV, Rhodes J. Convergence of Schiff base costimulatory signaling and TCR signaling at the level of mitogen-activated protein kinase ERK2. J Immunol. 1997 Sep 1;159(5):2274-81. PMID: 9278316.
13: Chen H, Rhodes J. Schiff base forming drugs: mechanisms of immune potentiation and therapeutic potential. J Mol Med (Berl). 1996 Sep;74(9):497-504. doi: 10.1007/BF00204975. PMID: 8892054.
14: Hall SR, Rhodes J. Schiff base-mediated co-stimulation primes the T-cell- receptor-dependent calcium signalling pathway in CD4 T cells. Immunology. 2001 Sep;104(1):50-7. doi: 10.1046/j.1365-2567.2001.01290.x. PMID: 11576220; PMCID: PMC1783279.
15: Chen H, Hall S, Zheng B, Rhodes J. BioDrugs. 1997 Mar;7(3):217-31. doi: 10.2165/00063030-199707030-00005. PMID: 18031095.
16: Singh G, Pai RS. Dawn of antioxidants and immune modulators to stop HIV- progression and boost the immune system in HIV/AIDS patients: An updated comprehensive and critical review. Pharmacol Rep. 2015 Jun;67(3):600-5. doi: 10.1016/j.pharep.2014.12.007. Epub 2014 Dec 24. PMID: 25933975.
17: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Apr;25(3):225-48. PMID: 12743628.
18: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jun;26(5):357-91. PMID: 15319815.
19: Charo J, Sundbäck M, Wasserman K, Ciupitu AM, Mirzai B, van der Zee R, Kiessling R. Marked enhancement of the antigen-specific immune response by combining plasmid DNA-based immunization with a Schiff base-forming drug. Infect Immun. 2002 Dec;70(12):6652-7. doi: 10.1128/iai.70.12.6652-6657.2002. PMID: 12438338; PMCID: PMC133029.
20: Fernández-Tejada A, Tan DS, Gin DY. Development of Improved Vaccine Adjuvants Based on the Saponin Natural Product QS-21 through Chemical Synthesis. Acc Chem Res. 2016 Sep 20;49(9):1741-56. doi: 10.1021/acs.accounts.6b00242. Epub 2016 Aug 28. PMID: 27568877; PMCID: PMC5032057.

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