-Glycosides of Indigo, Indirubin, and Isoindigo: Blue, Red, and Yellow Sugars and Their Cancerostatic Activity

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2024 Nov 12

PMID 39530076

Authors

Peter Langer

Affiliations

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Abstract

Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. -Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty. The present article provides an account on the synthesis and anticancer activity of these compounds.

References

Maskey R, Grun-Wollny I, Laatsch H . Isolation and structure elucidation of diazaquinomycin C from a terrestrial Streptomyces sp. and confirmation of the akashin structure. Nat Prod Res. 2005; 19(2):137-42. DOI: 10.1080/14786410410001704741. View

Bouchikhi F, Anizon F, Moreau P . Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives. Eur J Med Chem. 2007; 43(4):755-62. DOI: 10.1016/j.ejmech.2007.05.012. View

Soam P, Mandal D, Tyagi V . Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction. J Org Chem. 2023; 88(15):11023-11035. DOI: 10.1021/acs.joc.3c00994. View

Zhivkova V, Kiecker F, Langer P, Eberle J . Crucial role of reactive oxygen species (ROS) for the proapoptotic effects of indirubin derivative DKP-073 in melanoma cells. Mol Carcinog. 2018; 58(2):258-269. DOI: 10.1002/mc.22924. View

Huang C, Hecht S . A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools. Chemistry. 2023; 29(43):e202300981. DOI: 10.1002/chem.202300981. View

Berger A, Quast S, Plotz M, Hein M, Kunz M, Langer P . Sensitization of melanoma cells for death ligand-induced apoptosis by an indirubin derivative--Enhancement of both extrinsic and intrinsic apoptosis pathways. Biochem Pharmacol. 2010; 81(1):71-81. DOI: 10.1016/j.bcp.2010.09.010. View

Eberle J, Spangler B, Becker J, Heinemann S, Klein C, Kunz M . Multicentre study on standardisation of melanoma cell culture--an initiative of the German Melanoma Research Network. Pigment Cell Melanoma Res. 2010; 23(2):296-8. DOI: 10.1111/j.1755-148X.2010.00684.x. View

Fischle A, Schwarz R, Wendt F, Kordt M, Ramer R, Boeckmann L . A Sensitive LC-MS/MS Method for the Simultaneous Determination of Two Thia-Analogous Indirubin -Glycosides and Indirubin-3'-Monoxime in Plasma and Cell Culture Medium. Molecules. 2022; 27(9). PMC: 9101087. DOI: 10.3390/molecules27093031. View

Sassatelli M, Bouchikhi F, Aboab B, Anizon F, Fabbro D, Prudhomme M . In-vitro antiproliferative activities and kinase inhibitory potencies of glycosyl-isoindigo derivatives. Anticancer Drugs. 2007; 18(9):1069-74. DOI: 10.1097/CAD.0b013e328182d281. View

10.

Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G . Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship. Eur J Med Chem. 2021; 223:113652. DOI: 10.1016/j.ejmech.2021.113652. View

11.

Bogdanov A, Mironov V . Recent advances in the application of isoindigo derivatives in materials chemistry. Beilstein J Org Chem. 2021; 17:1533-1564. PMC: 8275870. DOI: 10.3762/bjoc.17.111. View

12.

Moon M, Lee S, Lee J, Song W, Kim S, Kim J . Synthesis and structure-activity relationships of novel indirubin derivatives as potent anti-proliferative agents with CDK2 inhibitory activities. Bioorg Med Chem. 2005; 14(1):237-46. DOI: 10.1016/j.bmc.2005.08.008. View

13.

Huang M, Lin H, Lee Y, Ho P . Evaluation of meisoindigo, an indirubin derivative: in vitro antileukemic activity and in vivo pharmacokinetics. Int J Oncol. 2014; 45(4):1724-34. DOI: 10.3892/ijo.2014.2548. View

14.

Xiao Z, Hao Y, Liu B, Qian L . Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China. Leuk Lymphoma. 2003; 43(9):1763-8. DOI: 10.1080/1042819021000006295. View

15.

Wendt F, Wittig F, Rupprecht A, Ramer R, Langer P, Emmert S . A Thia-Analogous Indirubin -Glycoside Disrupts Mitochondrial Function and Causes the Death of Human Melanoma and Cutaneous Squamous Cell Carcinoma Cells. Cells. 2023; 12(19). PMC: 10572502. DOI: 10.3390/cells12192409. View

16.

Karapetyan G, Chakrabarty K, Hein M, Langer P . Synthesis and bioactivity of carbohydrate derivatives of indigo, its isomers and heteroanalogues. ChemMedChem. 2010; 6(1):25-37. DOI: 10.1002/cmdc.201000374. View

17.

Boeckmann L, Berner J, Kordt M, Lenz E, Schafer M, Semmler M . Synergistic effect of cold gas plasma and experimental drug exposure exhibits skin cancer toxicity in vitro and in vivo. J Adv Res. 2023; 57:181-196. PMC: 10918357. DOI: 10.1016/j.jare.2023.06.014. View

18.

Kunz M, Driller K, Hein M, Libnow S, Hohensee I, Ramer R . Synthesis of thia-analogous indirubin N-Glycosides and their influence on melanoma cell growth and apoptosis. ChemMedChem. 2010; 5(4):534-9. DOI: 10.1002/cmdc.200900506. View

19.

Yang L, Li X, Huang W, Rao X, Lai Y . Pharmacological properties of indirubin and its derivatives. Biomed Pharmacother. 2022; 151:113112. DOI: 10.1016/j.biopha.2022.113112. View

20.

Kleeblatt D, Siyo B, Hein M, Iaroshenko V, Iqbal J, Villinger A . Synthesis of N,N'-diglycosylated isoindigos. Org Biomol Chem. 2013; 11(6):886-95. DOI: 10.1039/c2ob25866h. View