Isoindigotin
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MedKoo CAT#: 329478

CAS#: 476-34-6

Description: Isoindigotin is a potential antileukemic agent.

Chemical Structure

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Isoindigotin
CAS# 476-34-6
Instruction

Theoretical Analysis

MedKoo Cat#: 329478
Name: Isoindigotin
CAS#: 476-34-6
Chemical Formula: C16H10N2O2
Exact Mass: 262.07
Molecular Weight: 262.268
Elemental Analysis: C, 73.27; H, 3.84; N, 10.68; O, 12.20

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1250 Ready to ship
1g USD 2250 2 weeks
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Synonym: Isoindigotin

IUPAC/Chemical Name: (E)-[3,3'-biindolinylidene]-2,2'-dione

InChi Key: MLCPSWPIYHDOKG-BUHFOSPRSA-N

InChi Code: InChI=1S/C16H10N2O2/c19-15-13(9-5-1-3-7-11(9)17-15)14-10-6-2-4-8-12(10)18-16(14)20/h1-8H,(H,17,19)(H,18,20)/b14-13+

SMILES Code: O=C1NC2=C(C=CC=C2)/C1=C3C(NC4=C\3C=CC=C4)=O

Appearance: Red 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 262.27 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:

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1: Wu KM, Zhang MY, Fang Z, Huang L. [Potential antileukemic agents, synthesis of derivatives of indirubin, indigo, and isoindigotin]. Yao Xue Xue Bao. 1985 Nov;20(11):821-6. Chinese. PubMed PMID: 3869774.

2: Saleh AM, Aljada A, El-Abadelah MM, Sabri SS, Zahra JA, Nasr A, Aziz MA. The pyridone-annelated isoindigo (5'-Cl) induces apoptosis, dysregulation of mitochondria and formation of ROS in leukemic HL-60 cells. Cell Physiol Biochem. 2015;35(5):1958-74. doi: 10.1159/000374004. PubMed PMID: 25871324.

3: Saleh AM, Aljada A, El-Abadelah MM, Taha MO, Sabri SS, Zahra JA, Aziz MA. The anticancer activity of the substituted pyridone-annelated isoindigo (5'-Cl) involves G0/G1 cell cycle arrest and inactivation of CDKs in the promyelocytic leukemia cell line HL-60. Cell Physiol Biochem. 2015;35(5):1943-57. doi: 10.1159/000374003. PubMed PMID: 25870953.

4: Gui YY, Yang J, Qi LW, Wang X, Tian F, Li XN, Peng L, Wang LX. A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters. Org Biomol Chem. 2015 Jun 14;13(22):6371-9. doi: 10.1039/c5ob00774g. PubMed PMID: 25974840.

5: Saleh AM, El-Abadelah MM, Aziz MA, Taha MO, Nasr A, Rizvi SA. Antiproliferative activity of the isoindigo 5'-Br in HL-60 cells is mediated by apoptosis, dysregulation of mitochondrial functions and arresting cell cycle at G0/G1 phase. Cancer Lett. 2015 Jun 1;361(2):251-61. doi: 10.1016/j.canlet.2015.03.013. PubMed PMID: 25790909.

6: Zhao P, Li Y, Gao G, Wang S, Yan Y, Zhan X, Liu Z, Mao Z, Chen S, Wang L. Design, synthesis and biological evaluation of N-alkyl or aryl substituted isoindigo derivatives as potential dual cyclin-dependent kinase 2 (CDK2)/glycogen synthase kinase 3β (GSK-3β) phosphorylation inhibitors. Eur J Med Chem. 2014 Oct 30;86:165-74. doi: 10.1016/j.ejmech.2014.08.049. PubMed PMID: 25151579.

7: Saleh AM, Al-As'ad RM, El-Abadelah MM, Sabri SS, Zahra JA, Alaskar AS, Aljada A. Synthesis and biological evaluation of new pyridone-annelated isoindigos as anti-proliferative agents. Molecules. 2014 Aug 25;19(9):13076-92. doi: 10.3390/molecules190913076. PubMed PMID: 25157470.

8: Ren Y, Hiszpanski AM, Whittaker-Brooks L, Loo YL. Structure-property relationship study of substitution effects on isoindigo-based model compounds as electron donors in organic solar cells. ACS Appl Mater Interfaces. 2014 Aug 27;6(16):14533-42. doi: 10.1021/am503812f. PubMed PMID: 25089728; PubMed Central PMCID: PMC4149328.

9: Dang D, Chen W, Yang R, Zhu W, Mammo W, Wang E. Fluorine substitution enhanced photovoltaic performance of a D-A(1)-D-A(2) copolymer. Chem Commun (Camb). 2013 Oct 18;49(81):9335-7. doi: 10.1039/c3cc44931a. PubMed PMID: 24000353.

10: Kleeblatt D, Siyo B, Hein M, Iaroshenko VO, Iqbal J, Villinger A, Langer P. Synthesis of N,N'-diglycosylated isoindigos. Org Biomol Chem. 2013 Feb 14;11(6):886-95. doi: 10.1039/c2ob25866h. PubMed PMID: 23288204.

11: Wee XK, Yang T, Go ML. Exploring the anticancer activity of functionalized isoindigos: synthesis, drug-like potential, mode of action and effect on tumor-induced xenografts. ChemMedChem. 2012 May;7(5):777-91. doi: 10.1002/cmdc.201200018. PubMed PMID: 22416043.

12: Nishiumi S, Yamamoto N, Kodoi R, Fukuda I, Yoshida K, Ashida H. Antagonistic and agonistic effects of indigoids on the transformation of an aryl hydrocarbon receptor. Arch Biochem Biophys. 2008 Feb 15;470(2):187-99. PubMed PMID: 18086550.

13: Bouchikhi F, Anizon F, Moreau P. Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7'-azaisoindigo derivatives substituted by Sonogashira cross-coupling. Eur J Med Chem. 2009 Jun;44(6):2705-10. doi: 10.1016/j.ejmech.2009.01.027. PubMed PMID: 19232788.

14: Bouchikhi F, Anizon F, Moreau P. Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives. Eur J Med Chem. 2008 Apr;43(4):755-62. PubMed PMID: 17628214.

15: Perpète EA, Preat J, André JM, Jacquemin D. An ab initio study of the absorption spectra of indirubin, isoindigo, and related derivatives. J Phys Chem A. 2006 May 4;110(17):5629-35. PubMed PMID: 16640356.