Isoindigotin | CAS#476-34-6 | Antilukemic agent MedKoo

MedKoo Cat#: 329478 | Name: Isoindigotin

Description:

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

Isoindigotin is a structural isomer of indigotin (the main component of natural indigo dye), characterized by a different arrangement of the carbonyl and nitrogen atoms in its molecular framework. It features a conjugated system that gives it deep blue-violet pigmentation, and is used in dye chemistry and organic electronics for its chromophore properties. Though less common than indigotin, isoindigotin is of interest for its electronic and optical properties in applications such as semiconductors and photovoltaic materials.

Chemical Structure

Isoindigotin

CAS#476-34-6

Theoretical Analysis

MedKoo Cat#: 329478

Name: Isoindigotin

CAS#: 476-34-6

Chemical Formula: C16H10N2O2

Exact Mass: 262.0742

Molecular Weight: 262.27

Elemental Analysis: C, 73.27; H, 3.84; N, 10.68; O, 12.20

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,250.00	Ready to ship
1g	USD 2,250.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

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

Certificate of Analysis

View CoA: current batch, Lot#T7R10C26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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.

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

1: El-Abadelah MM, Abdullah AH, Zahra JA, Sabri SS, Bardaweel SK, Taha MO. Synthesis and antitumor activity of model cyclopentene-[g]annelated isoindigos. Z Naturforsch C J Biosci. 2024 Feb 29;79(1-2):41-46. doi: 10.1515/znc-2023-0119. PMID: 38414412. 2: Wang Y, Wang H, Deng J, Pan Y, Zheng Z, Ding X. Isoindigo-Based Dual-Acceptor Conjugated Polymers Incorporated Conjugation Length and Intramolecular Charge Transfer for High-Efficient Photothermal Conversion. Macromol Rapid Commun. 2023 Oct;44(19):e2300244. doi: 10.1002/marc.202300244. Epub 2023 Jul 25. PMID: 37465937. 3: Cao J, Luo X, Zhou S, Wu Z, Zhao Q, Gu H, Wang W, Zhang Z, Zhang K, Li K, Xu J, Liu X, Lu B, Lin K. Isoindigo-Thiophene D-A-D-Type Conjugated Polymers: Electrosynthesis and Electrochromic Performances. Int J Mol Sci. 2023 Jan 22;24(3):2219. doi: 10.3390/ijms24032219. PMID: 36768544; PMCID: PMC9916795. 4: Zhang Z, Sun Y, Zhao X, Jin N, Xi G, Zhang X, Cao J, Wu J, Fan X, Qin W. Novel isoindigo compound with aggregation-induced emission: Br-Br bonding joint restriction of intramolecular motion and cell imaging properties. Soft Matter. 2021 Nov 10;17(43):9866-9870. doi: 10.1039/d1sm00935d. PMID: 34724018. 5: Neophytou M, Bryant D, Lopatin S, Chen H, Hallani RK, Cater L, McCulloch I, Yue W. Alternative Thieno[3,2-b][1]benzothiophene Isoindigo Polymers for Solar Cell Applications. Macromol Rapid Commun. 2018 Jul;39(14):e1700820. doi: 10.1002/marc.201700820. Epub 2018 Mar 5. PMID: 29504170. 6: Li DD, Wang JX, Ma Y, Qian HS, Wang D, Wang L, Zhang G, Qiu L, Wang YC, Yang XZ. A Donor-Acceptor Conjugated Polymer with Alternating Isoindigo Derivative and Bithiophene Units for Near-Infrared Modulated Cancer Thermo-Chemotherapy. ACS Appl Mater Interfaces. 2016 Aug 3;8(30):19312-20. doi: 10.1021/acsami.6b05495. Epub 2016 Jul 20. PMID: 27404741. 7: 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. PMID: 25974840. 8: 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. Epub 2015 Mar 27. PMID: 25871324. 9: 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. Epub 2015 Mar 27. PMID: 25870953. 10: 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. Epub 2015 Mar 16. PMID: 25790909. 11: 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. PMID: 25157470; PMCID: PMC6271423. 12: 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. Epub 2014 Aug 15. PMID: 25151579. 13: 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. Epub 2014 Aug 12. PMID: 25089728; PMCID: PMC4149328. 14: 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. PMID: 24000353. 15: 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. Epub 2013 Jan 4. PMID: 23288204. 16: 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. Epub 2012 Mar 13. PMID: 22416043. 17: 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. Epub 2009 Feb 5. PMID: 19232788. 18: 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. doi: 10.1016/j.abb.2007.11.021. Epub 2007 Dec 7. PMID: 18086550. 19: 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. doi: 10.1016/j.ejmech.2007.05.012. Epub 2007 Jun 3. PMID: 17628214. 20: 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. doi: 10.1021/jp060069e. PMID: 16640356.

View History

Hetolin HCl

MedKoo CAT#: 413703

CAS#: 1949-07-1 (HCl)