Tucaresol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 462619

CAS#: 84290-27-7

Description: Tucaresol has been used in trials studying the treatment of HIV Infections.

Chemical Structure

img
Tucaresol
CAS# 84290-27-7
Instruction

Theoretical Analysis

MedKoo Cat#: 462619
Name: Tucaresol
CAS#: 84290-27-7
Chemical Formula: C15H12O5
Exact Mass: 272.07
Molecular Weight: 272.256
Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 589C; 589C80; BW 589C; BW A589C; BW-589C

IUPAC/Chemical Name: 4-((2-formyl-3-hydroxyphenoxy)methyl)benzoic acid

InChi Key: XEDONBRPTABQFB-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: OC(c1ccc(COc2c(C=O)c(O)ccc2)cc1)=O

Appearance: 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: >3 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 272.26 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.