Isatin | Tribulin | CAS#91-56-5 | MAO-B inhibitor | guanylate cyclase inhibitor

MedKoo Cat#: 540226 | Name: Isatin

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Description:

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

Isatin, also called Tribulin, is a MAO-B and guanylate cyclase inhibitor found in Istasis, Calanthe and Courouptia. It prevents TNBS-induced increases in pro-inflammatory cytokines and protects agains colitis-induced injuries. Derivatives may inhibit cancer cell growth.

Chemical Structure

Isatin

CAS#91-56-5

Theoretical Analysis

MedKoo Cat#: 540226

Name: Isatin

CAS#: 91-56-5

Chemical Formula: C8H5NO2

Exact Mass: 147.0320

Molecular Weight: 147.13

Elemental Analysis: C, 65.31; H, 3.43; N, 9.52; O, 21.75

Price and Availability

Size	Price	Availability	Quantity
5g	USD 150.00	2 Weeks
25g	USD 250.00	2 Weeks

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Synonym

Isatin; 2,3-Dioxo-2,3-dihydroindole; Isatic acid lactam; Isotin

IUPAC/Chemical Name

indoline-2,3-dione

InChi Key

JXDYKVIHCLTXOP-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

SMILES Code

O=C1NC2=C(C=CC=C2)C1=O

Appearance

Solid powder

Purity

>97% (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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Isatin (Indoline-2,3-dione) is a potent inhibitor of monoamine oxidase (MAO) with an IC50 of 3 μM. Also binds to central benzodiazepine receptors (IC50 against clonazepam, 123 μM). Also acts as an antagonist of both atrial natriuretic peptide stimulated and nitric oxide-stimulated guanylate cyclase activity. Shows effect on the serotonergic system.

In vitro activity:

Isatin inhibited the invasion and metastasis of NB cells in vitro. The growth inhibitory effects of isatin on SH-SY5Y cells were evaluated with a CCK-8 assay. As shown in Figure 1B, isatin at various concentrations influenced the survival rate of SH-SY5Y cells after treatment for 48/72 h. Reference: Int J Clin Exp Pathol. 2019 Jul 1;12(7):2446-2454. https://pubmed.ncbi.nlm.nih.gov/31934071/

In vivo activity:

Consistent with reduced oxidative stress and enhanced antioxidant capacity, isatin cotreatment significantly reduced hepatic MDA content and could increase both GSH content and SOD activity compared to rats administered DENA/2-AAF alone (Figure 3). Reference: Antioxidants (Basel). 2022 Apr 1;11(4):699. https://pubmed.ncbi.nlm.nih.gov/35453384/

	Solvent	mg/mL	mM
Solubility
	DMSO	69.5	472.36
	Ethanol	10.0	0.68

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 147.13 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. Cong S, Luo H, Li X, Wang F, Hua Y, Zhang L, Zhang Z, Li N, Hou L. Isatin inhibits SH-SY5Y neuroblastoma cell invasion and metastasis through PTEN signaling. Int J Clin Exp Pathol. 2019 Jul 1;12(7):2446-2454. PMID: 31934071; PMCID: PMC6949577. 2. Zhang Q, Fu Y, Zhao Y, Cui S, Wang J, Liu F, Yuan Y, Galons H, Yu P, Teng Y. 5-Acetamido-1-(methoxybenzyl) isatin inhibits tumor cell proliferation, migration, and angiogenesis. RSC Adv. 2019 Nov 11;9(63):36690-36698. doi: 10.1039/c9ra07002h. PMID: 35539063; PMCID: PMC9075125. 3. Tawfik NG, Mohamed WR, Mahmoud HS, Alqarni MA, Naguib IA, Fahmy AM, Ahmed OM. Isatin Counteracts Diethylnitrosamine/2-Acetylaminofluorene-Induced Hepatocarcinogenesis in Male Wistar Rats by Upregulating Anti-Inflammatory, Antioxidant, and Detoxification Pathways. Antioxidants (Basel). 2022 Apr 1;11(4):699. doi: 10.3390/antiox11040699. PMID: 35453384; PMCID: PMC9027254. 4. Medvedev A, Kopylov A, Buneeva O, Kurbatov L, Tikhonova O, Ivanov A, Zgoda V. A Neuroprotective Dose of Isatin Causes Multilevel Changes Involving the Brain Proteome: Prospects for Further Research. Int J Mol Sci. 2020 Jun 11;21(11):4187. doi: 10.3390/ijms21114187. PMID: 32545384; PMCID: PMC7313464.

In vitro protocol:

In vivo protocol:

1. Tawfik NG, Mohamed WR, Mahmoud HS, Alqarni MA, Naguib IA, Fahmy AM, Ahmed OM. Isatin Counteracts Diethylnitrosamine/2-Acetylaminofluorene-Induced Hepatocarcinogenesis in Male Wistar Rats by Upregulating Anti-Inflammatory, Antioxidant, and Detoxification Pathways. Antioxidants (Basel). 2022 Apr 1;11(4):699. doi: 10.3390/antiox11040699. PMID: 35453384; PMCID: PMC9027254. 2. Medvedev A, Kopylov A, Buneeva O, Kurbatov L, Tikhonova O, Ivanov A, Zgoda V. A Neuroprotective Dose of Isatin Causes Multilevel Changes Involving the Brain Proteome: Prospects for Further Research. Int J Mol Sci. 2020 Jun 11;21(11):4187. doi: 10.3390/ijms21114187. PMID: 32545384; PMCID: PMC7313464.

1: Sommer T, Bjerregaard-Andersen K, Simensen SM, Jensen JK, Jochimsen B, Riss PJ, Etzerodt M, Morth JP. Enzymatic detection and quantification assay of isatin, a putative stress biomarker in blood. ACS Chem Neurosci. 2015 Aug 19;6(8):1353-60. doi: 10.1021/cn500346x. Epub 2015 May 5. PubMed PMID: 25891478. 2: Dou X, Yao W, Jiang C, Lu Y. Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles. Chem Commun (Camb). 2014 Oct 7;50(77):11354-7. doi: 10.1039/c4cc04586f. PubMed PMID: 25163647. 3: Cigáň M, Jakusová K, Gáplovský M, Filo J, Donovalová J, Gáplovský A. Isatin phenylhydrazones: anion enhanced photochromic behaviour. Photochem Photobiol Sci. 2015 Nov;14(11):2064-73. doi: 10.1039/c5pp00275c. PubMed PMID: 26412034. 4: Pakravan P, Kashanian S, Khodaei MM, Harding FJ. Biochemical and pharmacological characterization of isatin and its derivatives: from structure to activity. Pharmacol Rep. 2013;65(2):313-35. Review. PubMed PMID: 23744416. 5: Phogat P, Singh P. A mini review on central nervous system potential of isatin derivatives. Cent Nerv Syst Agents Med Chem. 2015;15(1):28-31. Review. PubMed PMID: 25693647. 6: Gui Q, Dai F, Liu J, Chen P, Yang Z, Chen X, Tan Z. Synthesis of N-alkyl isatins via oxidative cyclization of N-alkyl 2-bromo(chloro)acetanilides. Org Biomol Chem. 2014 Jun 7;12(21):3349-53. doi: 10.1039/c4ob00118d. Epub 2014 Apr 17. PubMed PMID: 24740324. 7: Paladhi S, Bhati M, Panda D, Dash J. Thiazolidinedione-isatin conjugates via an uncatalyzed diastereoselective aldol reaction on water. J Org Chem. 2014 Feb 7;79(3):1473-80. doi: 10.1021/jo402515d. Epub 2014 Jan 9. PubMed PMID: 24383887. 8: Limpachayaporn P, Wagner S, Kopka K, Schober O, Schäfers M, Haufe G. Synthesis of 7-halogenated isatin sulfonamides: nonradioactive counterparts of caspase-3/-7 inhibitor-based potential radiopharmaceuticals for molecular imaging of apoptosis. J Med Chem. 2014 Nov 26;57(22):9383-95. doi: 10.1021/jm500718e. Epub 2014 Nov 14. PubMed PMID: 25358116. 9: Song J, Hou L, Ju C, Zhang J, Ge Y, Yue W. Isatin inhibits proliferation and induces apoptosis of SH-SY5Y neuroblastoma cells in vitro and in vivo. Eur J Pharmacol. 2013 Feb 28;702(1-3):235-41. doi: 10.1016/j.ejphar.2013.01.017. Epub 2013 Jan 29. PubMed PMID: 23376416. 10: Žari S, Kudrjashova M, Pehk T, Lopp M, Kanger T. Remote activation of the nucleophilicity of isatin. Org Lett. 2014 Mar 21;16(6):1740-3. doi: 10.1021/ol500421k. Epub 2014 Mar 10. PubMed PMID: 24611877. 11: Raj R, Gut J, Rosenthal PJ, Kumar V. 1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: synthesis and antimalarial evaluation. Bioorg Med Chem Lett. 2014 Feb 1;24(3):756-9. doi: 10.1016/j.bmcl.2013.12.109. Epub 2014 Jan 3. PubMed PMID: 24424135. 12: Ibrahim HS, Abou-Seri SM, Tanc M, Elaasser MM, Abdel-Aziz HA, Supuran CT. Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem. 2015 Oct 20;103:583-93. doi: 10.1016/j.ejmech.2015.09.021. Epub 2015 Sep 16. PubMed PMID: 26408817. 13: Ali AQ, Teoh SG, Salhin A, Eltayeb NE, Khadeer Ahamed MB, Abdul Majid AM. Synthesis of isatin thiosemicarbazones derivatives: in vitro anti-cancer, DNA binding and cleavage activities. Spectrochim Acta A Mol Biomol Spectrosc. 2014 May 5;125:440-8. doi: 10.1016/j.saa.2014.01.086. Epub 2014 Jan 29. PubMed PMID: 24607427. 14: Zhang HM, Dai H, Hanson PJ, Li H, Guo H, Ye X, Hemida MG, Wang L, Tong Y, Qiu Y, Liu S, Wang F, Song F, Zhang B, Wang JG, Zhang LX, Yang D. Antiviral activity of an isatin derivative via induction of PERK-Nrf2-mediated suppression of cap-independent translation. ACS Chem Biol. 2014 Apr 18;9(4):1015-24. doi: 10.1021/cb400775z. Epub 2014 Feb 18. PubMed PMID: 24547890. 15: Salah S, El-Wahab ZH, Farag RS, Mostafa MM. Synthesis, characterization and modeling structures of isatin-3-Girard T (IGT) and P (IGP) hydrazone complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:579-87. doi: 10.1016/j.saa.2014.01.082. Epub 2014 Jan 25. PubMed PMID: 24509535. 16: Nisha, Gut J, Rosenthal PJ, Kumar V. β-amino-alcohol tethered 4-aminoquinoline-isatin conjugates: synthesis and antimalarial evaluation. Eur J Med Chem. 2014 Sep 12;84:566-73. doi: 10.1016/j.ejmech.2014.07.064. Epub 2014 Jul 21. PubMed PMID: 25062007. 17: Farag AA. Synthesis and Antimicrobial Activity of 5-(morpholinosulfonyl)isatin Derivatives Incorporating a Thiazole Moiety. Drug Res (Stuttg). 2015 Jul;65(7):373-9. doi: 10.1055/s-0034-1384609. Epub 2014 Aug 12. PubMed PMID: 25116255. 18: Kumar A, Kaur J, Chauhan P, Chimni SS. Organocatalytic asymmetric Friedel-Crafts reaction of sesamol with isatins: access to biologically relevant 3-aryl-3-hydroxy-2-oxindoles. Chem Asian J. 2014 May;9(5):1305-10. doi: 10.1002/asia.201301546. Epub 2014 Mar 3. PubMed PMID: 24591414. 19: Kumar K, Pradines B, Madamet M, Amalvict R, Benoit N, Kumar V. 1H-1,2,3-triazole tethered isatin-ferrocene conjugates: Synthesis and in vitro antimalarial evaluation. Eur J Med Chem. 2014 Nov 24;87:801-4. doi: 10.1016/j.ejmech.2014.10.024. Epub 2014 Oct 13. PubMed PMID: 25440881. 20: Rane RA, Karunanidhi S, Jain K, Shaikh M, Hampannavar G, Karpoormath R. A Recent Perspective on Discovery and Development of Diverse Therapeutic Agents Inspired from Isatin Alkaloids. Curr Top Med Chem. 2016;16(11):1262-89. Review. PubMed PMID: 26369813.