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MedKoo Cat#: 561469 | Name: Coralyne chloride
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Description:

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

Coralyne chloride is a a protoberberine alkaloid, can be used as a fluorescent DNA-based molecular rectifier. Coralyne constructs into a DNA duplex by site-specific intercalation. Coralyne is a useful fluorescent probe for the sensitive and selective detection of heparin, DNA, nucleic acid, etc. Coralyne is also a promising antitumor and necurodrug.

Chemical Structure

Coralyne chloride
CAS#38989-38-7 (chloride)

Theoretical Analysis

MedKoo Cat#: 561469

Name: Coralyne chloride

CAS#: 38989-38-7 (chloride)

Chemical Formula: C22H22ClNO4

Exact Mass: 0.0000

Molecular Weight: 399.87

Elemental Analysis: C, 66.08; H, 5.55; Cl, 8.87; N, 3.50; O, 16.00

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to ship
10mg USD 160.00 Ready to ship
25mg USD 350.00 Ready to ship
50mg USD 550.00 Ready to ship
100mg USD 950.00 Ready to ship
200mg USD 1,650.00 Ready to ship
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Related CAS #
6872-73-7 (free base) 38989-37-6 (sulfoacetate) 38989-38-7 (chloride)
Synonym
Coralyne chloride; NSC 154890; NSC-154890; NSC154890;
IUPAC/Chemical Name
2,3,10,11-Tetramethoxy-8-methylisoquinolino[2,1-b]isoquinolin-7-ium chloride
InChi Key
PDYBUYVOPAJLKP-UHFFFAOYSA-M
InChi Code
InChI=1S/C22H22NO4.ClH/c1-13-16-11-21(26-4)20(25-3)10-15(16)8-18-17-12-22(27-5)19(24-2)9-14(17)6-7-23(13)18;/h6-12H,1-5H3;1H/q+1;/p-1
SMILES Code
CC1=C2C=C(OC)C(OC)=CC2=CC3=C4C=C(OC)C(OC)=CC4=CC=[N+]13.[Cl-]
Appearance
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:
Coralyne chloride acts as a potent topoisomerase I poison and induces Top I mediated DNA cleavage.
In vitro activity:
Next, this study determined the maximum non-toxic dose of coralyne on A549 cells using the propidium iodide short-term cytotoxicity assay and the long-term survival assay. Results showed no signs of significant toxicity when the coralyne was permanently available at concentrations ranging from 1 to 15 µM for up to 72 h. When the coralyne was washed from the medium after 24 h, the IC75 and IC50 values from the clonogenic survival assay after 10 days were calculated as ~ 25 µM and 50 µM, respectively. These results are in agreement with the earlier documented in vitro study using coralyne. The authors reported that metabolic activity of A549, MCF7, A431 and MDA-MB-231 was not decreased by the coralyne at concentrations ranging from 0.01 µM to 20 µM after 72 h. In line with these results, Bhattacharyya et al. found that the coralyne at concentrations ranging from 1 µM to 5 µM did not induce any cytotoxicity against U2-OS, A549 and A431 cancer cells after 72 h. Reference: Int J Mol Sci. 2021 May 28;22(11):5791. https://www.mdpi.com/1422-0067/22/11/5791/htm
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 5.0 12.50
Water 5.0 12.50
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 399.87 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:
1. Węgierek-Ciuk A, Arabski M, Ciepluch K, Brzóska K, Lisowska H, Czerwińska M, Stępkowski T, Lis K, Lankoff A. Coralyne Radiosensitizes A549 Cells by Upregulation of CDKN1A Expression to Attenuate Radiation Induced G2/M Block of the Cell Cycle. Int J Mol Sci. 2021 May 28;22(11):5791. doi: 10.3390/ijms22115791. PMID: 34071406. 2. Bhattacharyya R, Gupta P, Bandyopadhyay SK, Patro BS, Chattopadhyay S. Coralyne, a protoberberine alkaloid, causes robust photosenstization of cancer cells through ATR-p38 MAPK-BAX and JAK2-STAT1-BAX pathways. Chem Biol Interact. 2018 Apr 1;285:27-39. doi: 10.1016/j.cbi.2018.02.032. Epub 2018 Feb 24. PMID: 29486184.
In vitro protocol:
1. Węgierek-Ciuk A, Arabski M, Ciepluch K, Brzóska K, Lisowska H, Czerwińska M, Stępkowski T, Lis K, Lankoff A. Coralyne Radiosensitizes A549 Cells by Upregulation of CDKN1A Expression to Attenuate Radiation Induced G2/M Block of the Cell Cycle. Int J Mol Sci. 2021 May 28;22(11):5791. doi: 10.3390/ijms22115791. PMID: 34071406. 2. Bhattacharyya R, Gupta P, Bandyopadhyay SK, Patro BS, Chattopadhyay S. Coralyne, a protoberberine alkaloid, causes robust photosenstization of cancer cells through ATR-p38 MAPK-BAX and JAK2-STAT1-BAX pathways. Chem Biol Interact. 2018 Apr 1;285:27-39. doi: 10.1016/j.cbi.2018.02.032. Epub 2018 Feb 24. PMID: 29486184.
In vivo protocol:
TBD
1: Padmapriya K, Barthwal R. Nuclear magnetic resonance based structure of the protoberberine alkaloid coralyne and its self-association by spectroscopy techniques. J Pharm Anal. 2019 Dec;9(6):437-448. doi: 10.1016/j.jpha.2019.09.006. Epub 2019 Sep 26. PMID: 31890344; PMCID: PMC6931075. 2: Ma C, Chen M, He H, Chen L. Detection of coralyne and heparin by polymerase extension reaction using SYBR Green I. Mol Cell Probes. 2019 Aug;46:101423. doi: 10.1016/j.mcp.2019.101423. Epub 2019 Jul 16. PMID: 31323319. 3: Kumari S, Mohan MG, Shailender G, Badana AK, Malla RR. Synergistic enhancement of apoptosis by coralyne and paclitaxel in combination on MDA-MB-231 a triple-negative breast cancer cell line. J Cell Biochem. 2019 Oct;120(10):18104-18116. doi: 10.1002/jcb.29114. Epub 2019 Jun 6. PMID: 31172606. 4: Patro BS, Bhattacharyya R, Gupta P, Bandyopadhyay S, Chattopadhyay S. Mechanism of coralyne-mediated DNA photo-nicking process. J Photochem Photobiol B. 2019 May;194:140-148. doi: 10.1016/j.jphotobiol.2019.03.011. Epub 2019 Mar 21. PMID: 30954873. 5: Lee CY, Lin SW, Wu YH, Hsieh YZ. Combining DNA-stabilized silver nanocluster synthesis with exonuclease III amplification allows label-free detection of coralyne. Anal Chim Acta. 2018 Dec 26;1042:86-92. doi: 10.1016/j.aca.2018.08.030. Epub 2018 Aug 18. PMID: 30428992. 6: Wang Y, Sun X, Zeng J, Deng M, Li N, Chen Q, Zhu H, Liu F, Xing X. Label-free and sensitive detection assay for terminal deoxynucleotidyl transferase via polyadenosine-coralyne fluorescence enhancement strategy. Anal Biochem. 2019 Feb 15;567:85-89. doi: 10.1016/j.ab.2018.08.003. Epub 2018 Aug 26. PMID: 30157446. 7: Bhattacharyya R, Gupta P, Bandyopadhyay SK, Patro BS, Chattopadhyay S. Coralyne, a protoberberine alkaloid, causes robust photosenstization of cancer cells through ATR-p38 MAPK-BAX and JAK2-STAT1-BAX pathways. Chem Biol Interact. 2018 Apr 1;285:27-39. doi: 10.1016/j.cbi.2018.02.032. Epub 2018 Feb 24. PMID: 29486184. 8: Bhattacharyya R, Saha B, Tyagi M, Bandyopadhyay SK, Patro BS, Chattopadhyay S. Differential modes of photosensitisation in cancer cells by berberine and coralyne. Free Radic Res. 2017 Jul-Aug;51(7-8):723-738. doi: 10.1080/10715762.2017.1368506. Epub 2017 Sep 5. PMID: 28870132. 9: Pithan PM, Decker D, Druzhinin SI, Ihmels H, Schönherr H, Voß Y. 8-Styryl- substituted coralyne derivatives as DNA binding fluorescent probes. RSC Adv. 2017 Feb 8;7(18):10660-10667. doi: 10.1039/c6ra27684a. PMID: 28496973; PMCID: PMC5361113. 10: Kumari S, Badana AK, Mohan GM, Shailender Naik G, Malla R. Synergistic effects of coralyne and paclitaxel on cell migration and proliferation of breast cancer cells lines. Biomed Pharmacother. 2017 Jul;91:436-445. doi: 10.1016/j.biopha.2017.04.027. Epub 2017 May 2. PMID: 28475922. 11: Padmapriya K, Barthwal R. NMR based structural studies decipher stacking of the alkaloid coralyne to terminal guanines at two different sites in parallel G-quadruplex DNA, [d(TTGGGGT)]4 and [d(TTAGGGT)]4. Biochim Biophys Acta Gen Subj. 2017 Feb;1861(2):37-48. doi: 10.1016/j.bbagen.2016.11.011. Epub 2016 Nov 10. PMID: 27838396. 12: Padmapriya K, Barthwal R. Binding of the alkaloid coralyne to parallel G-quadruplex DNA [d(TTGGGGT)]4 studied by multi-spectroscopic techniques. Biophys Chem. 2016 Dec;219:49-58. doi: 10.1016/j.bpc.2016.09.006. Epub 2016 Oct 1. PMID: 27721081. 13: Padmapriya K, Barthwal R. Nuclear magnetic resonance studies reveal stabilization of parallel G-quadruplex DNA [d(T2G4T)]4 upon binding to protoberberine alkaloid coralyne. Bioorg Med Chem Lett. 2016 Oct 15;26(20):4915-4918. doi: 10.1016/j.bmcl.2016.09.016. Epub 2016 Sep 7. PMID: 27624081. 14: Kim KT, Choi TS, Kim KY, Kim HI, Kim BH. Disassembly of Chromophore-Guided DNA Duplexes through Site-Selective Binding of Coralyne to Pyrene-Modified Adenine Bases. Chempluschem. 2016 Jul;81(7):590-593. doi: 10.1002/cplu.201600230. Epub 2016 May 31. PMID: 31968721. 15: Li JJ, Xi Q, Du WF, Yu RQ, Jiang JH. Label-free fluorescence detection of microRNA based on target induced adenosine2-coralyne-adenosine2 formation. Analyst. 2016 Apr 21;141(8):2384-7. doi: 10.1039/c6an00001k. Epub 2016 Mar 21. PMID: 26998900. 16: Huang H, Shi S, Zheng X, Yao T. Sensitive detection for coralyne and mercury ions based on homo-A/T DNA by exonuclease signal amplification. Biosens Bioelectron. 2015 Sep 15;71:439-444. doi: 10.1016/j.bios.2015.04.076. Epub 2015 Apr 24. PMID: 25950941. 17: Chen M , Yang S , He X , Wang K , Qiu P , He D . Co-loading of coralyne and indocyanine green into adenine DNA-functionalized mesoporous silica nanoparticles for pH- and near-infrared-responsive chemothermal treatment of cancer cells. J Mater Chem B. 2014 Sep 28;2(36):6064-6071. doi: 10.1039/c4tb01040j. Epub 2014 Aug 6. PMID: 32261858. 18: Wang G, Zhu Y, Chen L, Zhang X. Dual hairpin-like molecular beacon based on coralyne-adenosine interaction for sensing melamine in dairy products. Talanta. 2014 Nov;129:398-403. doi: 10.1016/j.talanta.2014.05.046. Epub 2014 Jun 11. PMID: 25127611. 19: Zheng Y, Zhou J, Sayre DA, Sintim HO. Identification of bromophenol thiohydantoin as an inhibitor of DisA, a c-di-AMP synthase, from a 1000 compound library, using the coralyne assay. Chem Commun (Camb). 2014 Oct 4;50(76):11234-7. doi: 10.1039/c4cc02916j. PMID: 25116237. 20: Kan Y, Jiang C, Xi Q, Wang X, Peng L, Jiang J, Yu R. A simple, sensitive colorimetric assay for coralyne based on target induced split G-quadruplex formation. Anal Sci. 2014;30(5):561-8. doi: 10.2116/analsci.30.561. PMID: 24813954.

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