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MedKoo Cat#: 145806 | Name: Tryptanthrine

Description:

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

Tryptanthrine is a naturally occurring alkaloid found in various plants, particularly those in the Indigofera genus. It is known for its potential antimicrobial and anti-inflammatory properties. Tryptanthrine has been studied for its effects on a range of biological systems, and research suggests it may have applications in treating infections or reducing inflammation. Additionally, it is of interest for its anticancer and antioxidant activities, although much of the research is still in early stages.

Chemical Structure

Tryptanthrine
Tryptanthrine
CAS#13220-57-0

Theoretical Analysis

MedKoo Cat#: 145806

Name: Tryptanthrine

CAS#: 13220-57-0

Chemical Formula: C23H12Cl2F2N2O5

Exact Mass: 504.0100

Molecular Weight: 505.25

Elemental Analysis: C, 54.68; H, 2.39; Cl, 14.03; F, 7.52; N, 5.54; O, 15.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Tryptanthrine; Tryptanthrin; NSC-349447; NSC349447; NSC 349447; Triptantrin;
IUPAC/Chemical Name
indolo[2,1-b]quinazoline-6,12-dione
InChi Key
VQQVWGVXDIPORV-UHFFFAOYSA-N
InChi Code
1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
SMILES Code
O=C1C2=NC3=C(C=CC=C3)C(=O)N2C4=C1C=CC=C4
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 505.25 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
1: Kaur R, Manjal SK, Rawal RK, Kumar K. Recent synthetic and medicinal perspectives of tryptanthrin. Bioorg Med Chem. 2017 Sep 1;25(17):4533-4552. doi: 10.1016/j.bmc.2017.07.003. Epub 2017 Jul 4. PMID: 28720329. 2: Ren L, Yang H, Wang H, Qin S, Zhan X, Li H, Wei Z, Fang Z, Li Q, Liu T, Shi W, Zhao J, Li Z, Bai Z, Xu G, Zhao J. Tryptanthrin suppresses multiple inflammasome activation to regulate NASH progression by targeting ASC protein. Phytomedicine. 2024 Aug;131:155758. doi: 10.1016/j.phymed.2024.155758. Epub 2024 May 28. PMID: 38843643. 3: Plotnikov MB, Chernysheva GA, Smol'yakova VI, Aliev OI, Kovrizhina AR, Khlebnikov AI, Drozd AG, Plotnikov EV. Antioxidant Effects of Tryptanthrin Oxime. Bull Exp Biol Med. 2024 Oct;177(6):741-744. doi: 10.1007/s10517-024-06261-2. Epub 2024 Oct 23. PMID: 39441442. 4: Zhang Y, Xiao B, Yuan S, Ding L, Pan Y, Jiang Y, Sun S, Ke X, Cai L, Jia L. Tryptanthrin targets GSTP1 to induce senescence and increases the susceptibility to apoptosis by senolytics in liver cancer cells. Redox Biol. 2024 Oct;76:103323. doi: 10.1016/j.redox.2024.103323. Epub 2024 Aug 20. PMID: 39180983; PMCID: PMC11388193. 5: Schindler F, Zähner H. Tryptanthrin, ein antibiotisch wirksames Tryptophanderivat aus Candida lipolytica (Kurzfassung [Tryptanthrine, an antibiotic tryptophan derivative from Candida lipolytica (brief report)]. Zentralbl Bakteriol Orig A. 1972 May;220(1):457. German. PMID: 4145624. 6: He Y, Yue J, Teng Y, Fan Z, Jia M, Teng H, Zhuge L. Tryptanthrin promotes pressure ulcers healing in mice by inhibiting macrophage-mediated inflammation via cGAS/STING pathways. Int Immunopharmacol. 2024 Mar 30;130:111687. doi: 10.1016/j.intimp.2024.111687. Epub 2024 Feb 21. PMID: 38382260. 7: Jahng Y. Progress in the studies on tryptanthrin, an alkaloid of history. Arch Pharm Res. 2013 May;36(5):517-35. doi: 10.1007/s12272-013-0091-9. Epub 2013 Mar 31. PMID: 23543631. 8: Narkhede RR, Pise AV, Cheke RS, Shinde SD. Recognition of Natural Products as Potential Inhibitors of COVID-19 Main Protease (Mpro): In-Silico Evidences. Nat Prod Bioprospect. 2020 Oct;10(5):297-306. doi: 10.1007/s13659-020-00253-1. Epub 2020 Jun 17. PMID: 32557405; PMCID: PMC7299459. 9: Wang C, Yang P, Wang J, Liu L, Chen J, Cai X, Zhang M, Lin N, Wang S, Yu Y, Li L, Li X. Evidence and potential mechanism of action of indigo naturalis and its active components in the treatment of psoriasis. Ann Med. 2024 Dec;56(1):2329261. doi: 10.1080/07853890.2024.2329261. Epub 2024 Sep 24. PMID: 39316667; PMCID: PMC11423532. 10: Gajos-Michniewicz A, Czyz M. Modulation of WNT/β-catenin pathway in melanoma by biologically active components derived from plants. Fitoterapia. 2016 Mar;109:283-92. doi: 10.1016/j.fitote.2016.02.002. Epub 2016 Feb 2. PMID: 26851176. 11: Pinheiro D, Pineiro M, Seixas de Melo JS. Tryptanthrin derivatives as efficient singlet oxygen sensitizers. Photochem Photobiol Sci. 2022 May;21(5):645-658. doi: 10.1007/s43630-021-00117-8. Epub 2021 Nov 4. PMID: 34735707. 12: Numao N, Kawaguchi S, Ding J, Karasawa T, Seya K, Matsumiya T, Kikuchi H, Sakuraba H, Fukuda S, Imaizumi T. Tryptanthrin attenuates TLR3-mediated STAT1 activation in THP-1 cells. Immunol Res. 2022 Oct;70(5):688-697. doi: 10.1007/s12026-022-09301-z. Epub 2022 Jun 6. PMID: 35666435; PMCID: PMC9169444. 13: Scovill J, Blank E, Konnick M, Nenortas E, Shapiro T. Antitrypanosomal activities of tryptanthrins. Antimicrob Agents Chemother. 2002 Mar;46(3):882-3. doi: 10.1128/AAC.46.3.882-883.2002. PMID: 11850279; PMCID: PMC127471. 14: Elsohly MA, Gul W. Recent patent reviews on small molecule-based antimalarial drugs. Recent Pat Antiinfect Drug Discov. 2007 Nov;2(3):222-32. doi: 10.2174/157489107782497263. PMID: 18221180. 15: Rasmussen LE, Lee TD, Daves GD Jr, Schmidt MJ. Female-to-male sex pheromones of low volatility in the Asian elephant,Elephas maximus. J Chem Ecol. 1993 Oct;19(10):2115-28. doi: 10.1007/BF00979651. PMID: 24248563. 16: Oberthür C, Hoffmann B, Hamburger M. Synthesis of d-tryptanthrin. Pharmazie. 2002 Aug;57(8):586-7. PMID: 12227204. 17: Zhang S, Qi F, Fang X, Yang D, Hu H, Huang Q, Kuang C, Yang Q. Tryptophan 2,3-dioxygenase inhibitory activities of tryptanthrin derivatives. Eur J Med Chem. 2018 Dec 5;160:133-145. doi: 10.1016/j.ejmech.2018.10.017. Epub 2018 Oct 10. PMID: 30321802. 18: Long X, Zhang G, Long H, Wang Q, Wang C, Zhu M, Wang W, Li C, Wang Z, Ouyang G. Discovery and Mechanism of Novel 7-Aliphatic Amine Tryptanthrin Derivatives against Phytopathogenic Bacteria. Int J Mol Sci. 2023 Jun 30;24(13):10900. doi: 10.3390/ijms241310900. PMID: 37446077; PMCID: PMC10341529. 19: Han NR, Park HJ, Ko SG, Moon PD. Tryptanthrin Down-Regulates Oncostatin M by Targeting GM-CSF-Mediated PI3K-AKT-NF-κB Axis. Nutrients. 2024 Nov 28;16(23):4109. doi: 10.3390/nu16234109. PMID: 39683503; PMCID: PMC11643981. 20: Schepetkin IA, Karpenko OS, Kovrizhina AR, Kirpotina LN, Khlebnikov AI, Chekal SI, Radudik AV, Shybinska MO, Quinn MT. Novel Tryptanthrin Derivatives with Selectivity as c-Jun N-Terminal Kinase (JNK) 3 Inhibitors. Molecules. 2023 Jun 16;28(12):4806. doi: 10.3390/molecules28124806. PMID: 37375361; PMCID: PMC10304880.

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