Indican | CAS#1328-73-0 | dye

MedKoo Cat#: 562045 | Name: Indican

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Description:

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

Indican is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. It is a precursor of indigo dye. Indican is a glycoside. Its hydrolysis yields β-D-glucose and indoxyl. Reaction of indoxyl (indican) by a mild oxidizing agent, e.g. atmospheric oxygen, yields indigo dye which is blue in colour.

Chemical Structure

Indican

CAS#487-60-5

Theoretical Analysis

MedKoo Cat#: 562045

Name: Indican

CAS#: 487-60-5

Chemical Formula: C14H17NO6

Exact Mass: 295.1056

Molecular Weight: 295.29

Elemental Analysis: C, 56.95; H, 5.80; N, 4.74; O, 32.51

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 550.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,650.00	2 Weeks
2g	USD 2,950.00	2 Weeks

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Related CAS #

1328-73-0 (trihydrate) 487-60-5

Synonym

Indican; NSC-87517; NSC 87517; NSC87517;

IUPAC/Chemical Name

(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol

InChi Key

XVARCVCWNFACQC-RKQHYHRCSA-N

InChi Code

InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1

SMILES Code

O[C@@H]1[C@@H](CO)O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@H]1O

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

>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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Indican (Indoxyl-β-D-glucoside), a glycoside of indoxyl, is a precursor of the dyesindigo and indirubin. Indican has a major metabolite, indoxyl sulfate (IS). IS, an uremic toxin, is a substrate/inhibitor of organic anion transporter (OAT) 1, OAT 3 and multidrug resistance-associated protein (MRP) 4.

In vitro activity:

In Figure 2C, in differentiated THP-1 (dTHP1: human monocyte-derived macrophages) cells, IS (indoxyl sulfate) induced the activation of mTORC1 and increased the expression of pro-inflammatory cytokines (TNF-α and IL-6), and these effects were also suppressed by the presence of rapamycin. These results suggest that IS induces the epithelial–mesenchymal transition of tubular epithelial cells, myofibroblast differentiation from fibroblasts, and inflammatory responses in macrophages through mTORC1 activation. Reference: Toxins (Basel). 2021 Dec 18;13(12):909. https://pubmed.ncbi.nlm.nih.gov/34941746/

In vivo activity:

An increased expression of REST protein (p < 0.05, Figures 6D, ,6E)6E) and mRNA (p < 0.05, Figure 6I) was found in the brains of indoxyl sulfate-treated mice and this elevation was decreased by AST-120 (p < 0.05, Figures 6D, ,6E,6E, ,6I).6I). The mRNA level of REST downstream of the Synaptosomal-Associated Protein 25 (SNAP-25) gene was decreased in indoxyl sulfate-treated mice (p < 0.05, Figure 6J). Its downregulation was alleviated by AST-120 (p < 0.05, Figure 6J). These findings suggest that indoxyl sulfate has inhibitory effects on BDNF and serotonin expression, and also induces corticosterone release. In addition, intracellular signaling and the reduction in BDNF and serotonin expression can be improved by AST-120. Reference: Aging (Albany NY). 2021 Feb 17;13(5):6681-6701. https://pubmed.ncbi.nlm.nih.gov/33621199/

	Solvent	mg/mL	mM
Solubility
	DMF	2.0	6.77
	DMSO	51.5	174.40
	Ethanol	3.0	10.16
	PBS (pH 7.2)	2.0	6.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 295.29 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.

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. Nakano T, Watanabe H, Imafuku T, Tokumaru K, Fujita I, Arimura N, Maeda H, Tanaka M, Matsushita K, Fukagawa M, Maruyama T. Indoxyl Sulfate Contributes to mTORC1-Induced Renal Fibrosis via The OAT/NADPH Oxidase/ROS Pathway. Toxins (Basel). 2021 Dec 18;13(12):909. doi: 10.3390/toxins13120909. PMID: 34941746; PMCID: PMC8706756. 2. Salyers ZR, Coleman M, Balestrieri NP, Ryan TE. Indoxyl sulfate impairs angiogenesis via chronic aryl hydrocarbon receptor activation. Am J Physiol Cell Physiol. 2021 Feb 1;320(2):C240-C249. doi: 10.1152/ajpcell.00262.2020. Epub 2021 Jan 6. PMID: 33406025; PMCID: PMC7948007. 3. Sun CY, Li JR, Wang YY, Lin SY, Ou YC, Lin CJ, Wang JD, Liao SL, Chen CJ. Indoxyl sulfate caused behavioral abnormality and neurodegeneration in mice with unilateral nephrectomy. Aging (Albany NY). 2021 Feb 17;13(5):6681-6701. doi: 10.18632/aging.202523. Epub 2021 Feb 17. PMID: 33621199; PMCID: PMC7993681. 4. Yabuuchi N, Hou H, Gunda N, Narita Y, Jono H, Saito H. Suppressed Hepatic Production of Indoxyl Sulfate Attenuates Cisplatin-Induced Acute Kidney Injury in Sulfotransferase 1a1-Deficient Mice. Int J Mol Sci. 2021 Feb 10;22(4):1764. doi: 10.3390/ijms22041764. PMID: 33578912; PMCID: PMC7916706.

In vitro protocol:

In vivo protocol:

1. Sun CY, Li JR, Wang YY, Lin SY, Ou YC, Lin CJ, Wang JD, Liao SL, Chen CJ. Indoxyl sulfate caused behavioral abnormality and neurodegeneration in mice with unilateral nephrectomy. Aging (Albany NY). 2021 Feb 17;13(5):6681-6701. doi: 10.18632/aging.202523. Epub 2021 Feb 17. PMID: 33621199; PMCID: PMC7993681. 2. Yabuuchi N, Hou H, Gunda N, Narita Y, Jono H, Saito H. Suppressed Hepatic Production of Indoxyl Sulfate Attenuates Cisplatin-Induced Acute Kidney Injury in Sulfotransferase 1a1-Deficient Mice. Int J Mol Sci. 2021 Feb 10;22(4):1764. doi: 10.3390/ijms22041764. PMID: 33578912; PMCID: PMC7916706.

1: Prokopienko AJ, Nolin TD. Microbiota-derived uremic retention solutes: perpetrators of altered nonrenal drug clearance in kidney disease. Expert Rev Clin Pharmacol. 2018 Jan;11(1):71-82. doi: 10.1080/17512433.2018.1378095. Epub 2017 Sep 20. Review. PubMed PMID: 28905671. 2: Kamiński T, Michałowska M, Pawlak D. Aryl hydrocarbon receptor (AhR) and its endogenous agonist - indoxyl sulfate in chronic kidney disease. Postepy Hig Med Dosw (Online). 2017 Jul 30;71(0):624-632. Review. PubMed PMID: 28791957. 3: Gao H, Liu S. Role of uremic toxin indoxyl sulfate in the progression of cardiovascular disease. Life Sci. 2017 Sep 15;185:23-29. doi: 10.1016/j.lfs.2017.07.027. Epub 2017 Jul 25. Review. PubMed PMID: 28754616. 4: Wu CC, Hung SC, Kuo KL, Tarng DC. Impact of Indoxyl Sulfate on Progenitor Cell-Related Neovascularization of Peripheral Arterial Disease and Post-Angioplasty Thrombosis of Dialysis Vascular Access. Toxins (Basel). 2017 Jan 7;9(1). pii: E25. doi: 10.3390/toxins9010025. Review. PubMed PMID: 28067862; PubMed Central PMCID: PMC5308257. 5: Niwa T. The role of carbon adsorbent in the conservative management of chronic kidney disease. Panminerva Med. 2017 Jun;59(2):139-148. doi: 10.23736/S0031-0808.16.03272-9. Epub 2016 Dec 16. Review. PubMed PMID: 27990791. 6: Yamaguchi J, Tanaka T, Inagi R. Effect of AST-120 in Chronic Kidney Disease Treatment: Still a Controversy? Nephron. 2017;135(3):201-206. doi: 10.1159/000453673. Epub 2016 Dec 14. Review. PubMed PMID: 27960172. 7: Leong SC, Sirich TL. Indoxyl Sulfate-Review of Toxicity and Therapeutic Strategies. Toxins (Basel). 2016 Nov 30;8(12). pii: E358. Review. PubMed PMID: 27916890; PubMed Central PMCID: PMC5198552. 8: Liabeuf S, Villain C, Massy ZA. Protein-bound toxins: has the Cinderella of uraemic toxins turned into a princess? Clin Sci (Lond). 2016 Dec 1;130(23):2209-2216. Review. PubMed PMID: 27799624. 9: Tan X, Cao X, Zou J, Shen B, Zhang X, Liu Z, Lv W, Teng J, Ding X. Indoxyl sulfate, a valuable biomarker in chronic kidney disease and dialysis. Hemodial Int. 2017 Apr;21(2):161-167. doi: 10.1111/hdi.12483. Epub 2016 Sep 12. Review. PubMed PMID: 27616754. 10: Al Khodor S, Shatat IF. Gut microbiome and kidney disease: a bidirectional relationship. Pediatr Nephrol. 2017 Jun;32(6):921-931. doi: 10.1007/s00467-016-3392-7. Epub 2016 Apr 29. Review. PubMed PMID: 27129691; PubMed Central PMCID: PMC5399049. 11: Ellis RJ, Small DM, Vesey DA, Johnson DW, Francis R, Vitetta L, Gobe GC, Morais C. Indoxyl sulphate and kidney disease: Causes, consequences and interventions. Nephrology (Carlton). 2016 Mar;21(3):170-7. doi: 10.1111/nep.12580. Review. PubMed PMID: 26239363. 12: Lin CJ, Wu V, Wu PC, Wu CJ. Meta-Analysis of the Associations of p-Cresyl Sulfate (PCS) and Indoxyl Sulfate (IS) with Cardiovascular Events and All-Cause Mortality in Patients with Chronic Renal Failure. PLoS One. 2015 Jul 14;10(7):e0132589. doi: 10.1371/journal.pone.0132589. eCollection 2015. Review. PubMed PMID: 26173073; PubMed Central PMCID: PMC4501756. 13: Lekawanvijit S, Krum H. Cardiorenal syndrome: role of protein-bound uremic toxins. J Ren Nutr. 2015 Mar;25(2):149-54. doi: 10.1053/j.jrn.2014.10.009. Epub 2014 Dec 31. Review. PubMed PMID: 25556308. 14: Barisione C, Ghigliotti G, Canepa M, Balbi M, Brunelli C, Ameri P. Indoxyl sulfate: a candidate target for the prevention and treatment of cardiovascular disease in chronic kidney disease. Curr Drug Targets. 2015;16(4):366-72. Review. PubMed PMID: 25537654. 15: Barreto FC, Stinghen AE, de Oliveira RB, Franco AT, Moreno AN, Barreto DV, Pecoits-Filho R, Drüeke TB, Massy ZA. The quest for a better understanding of chronic kidney disease complications: an update on uremic toxins. J Bras Nefrol. 2014 Apr-Jun;36(2):221-35. Review. English, Portuguese. PubMed PMID: 25055363. 16: Vanholder R, Schepers E, Pletinck A, Nagler EV, Glorieux G. The uremic toxicity of indoxyl sulfate and p-cresyl sulfate: a systematic review. J Am Soc Nephrol. 2014 Sep;25(9):1897-907. doi: 10.1681/ASN.2013101062. Epub 2014 May 8. Review. PubMed PMID: 24812165; PubMed Central PMCID: PMC4147984. 17: Ito S, Yoshida M. Protein-bound uremic toxins: new culprits of cardiovascular events in chronic kidney disease patients. Toxins (Basel). 2014 Feb 20;6(2):665-78. doi: 10.3390/toxins6020665. Review. PubMed PMID: 24561478; PubMed Central PMCID: PMC3942758. 18: Stockler-Pinto MB, Fouque D, Soulage CO, Croze M, Mafra D. Indoxyl sulfate and p-cresyl sulfate in chronic kidney disease. Could these toxins modulate the antioxidant Nrf2-Keap1 pathway? J Ren Nutr. 2014 Sep;24(5):286-91. doi: 10.1053/j.jrn.2013.11.006. Epub 2014 Jan 28. Review. PubMed PMID: 24480117. 19: Niwa T. Targeting protein-bound uremic toxins in chronic kidney disease. Expert Opin Ther Targets. 2013 Nov;17(11):1287-301. doi: 10.1517/14728222.2013.829456. Epub 2013 Aug 13. Review. PubMed PMID: 23941498. 20: Watanabe H. Molecular mechanisms for uremic toxin-induced oxidative tissue damage via a cardiovascular-renal connection. Yakugaku Zasshi. 2013;133(8):889-95. Review. Japanese. PubMed PMID: 23903229.