Dracorhodin Perchlorate | CAS# 125536-25-6 | Biochemical

MedKoo Cat#: 573990 | Name: Dracorhodin Perchlorate

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Description:

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

Dracorhodin Perchlorate is a pro-apoptotic compound and a synthetic analog of dracorhodin, an anthocyanin. It induces cell cycle arrest at the G0/G1 phase as well as apoptosis in U87MG and T98G glioma cells when used at concentrations of 40 and 80 μM. It also increases levels of p53, p21, Bim, and Bax and decreases levels of Bcl-2 in glioma cells in vitro. Dracorhodin perchlorate is cytotoxic to U937, A375-S2, and MCF-7 cells in a concentration-dependent manner. It is also cytotoxic to HeLa cells, an effect that can be reversed by Ac-YVAD-CMK, Z-DEVD-FMK, Z-IETD-FMK, and Z-LEHD-FMK, which are inhibitors of caspase-1, -3, -8, and -9, respectively.

Chemical Structure

Dracorhodin Perchlorate

CAS#125536-25-6

Theoretical Analysis

MedKoo Cat#: 573990

Name: Dracorhodin Perchlorate

CAS#: 125536-25-6

Chemical Formula: C17H15ClO7

Exact Mass: 366.0506

Molecular Weight: 366.75

Elemental Analysis: C, 55.67; H, 4.12; Cl, 9.67; O, 30.54

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 650.00	2 Weeks
100mg	USD 1,050.00	2 Weeks

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Synonym

Dracorhodin perchlorate; Dracorhodin perochlorate; Dracohodin perochlorate

IUPAC/Chemical Name

7-hydroxy-5-methoxy-6-methyl-2-phenyl-1-benzopyrylium, monoperchlorate

InChi Key

KRTYZFUODYMZPG-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H14O3.ClHO4/c1-11-14(18)10-16-13(17(11)19-2)8-9-15(20-16)12-6-4-3-5-7-12;2-1(3,4)5/h3-10H,1-2H3;(H,2,3,4,5)

SMILES Code

OC1=C(C)C(OC)=C(C=CC(C2=CC=CC=C2)=[O+]3)C3=C1.O=Cl([O-])(=O)=O

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

>3 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dracorhodin perchlorate inhibits cell proliferation and induces cell cycle arrest and apoptosis.

In vitro activity:

Quantitative data indicated that dracorhodin perchlorate at 1 µg/ml significantly reduced the wound width at the time point of 24 h and markedly promoted HaCaT cell migration compared with those in control cells (Fig. 2C). Therefore, this suggests that dracorhodin perchlorate enhanced cell migration in HaCaT keratinocytes. Reference: Exp Ther Med. 2021 Aug;22(2):822. https://pubmed.ncbi.nlm.nih.gov/34131445/

In vivo activity:

DP (dracorhodin perchlorate) treatment alleviated the prolonged inflammatory cell infiltration time and the increase in the TLR4 pathway and inflammatory factors caused by diabetes. DP also promoted wound healing by increasing eNOS protein expression and NO content in the later stage of wound healing. DP promotes wound healing in diabetic rats by regulating the TLR4 pathway and related inflammatory factors. Reference: Evid Based Complement Alternat Med. 2022 Apr 14;2022:9050686. https://pubmed.ncbi.nlm.nih.gov/35463063/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	81.80
	DMSO	65.0	177.23
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.55

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 366.75 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

Formulation protocol:

1. Lu CC, Yang JS, Chiu YJ, Tsai FJ, Hsu YM, Yin MC, Juan YN, Ho TJ, Chen HP. Dracorhodin perchlorate enhances wound healing via β-catenin, ERK/p38, and AKT signaling in human HaCaT keratinocytes. Exp Ther Med. 2021 Aug;22(2):822. doi: 10.3892/etm.2021.10254. Epub 2021 Jun 2. PMID: 34131445; PMCID: PMC8193218. 2. Liu Y, Wang Z, Ma C, Wei Z, Chen K, Wang C, Zhou C, Chen L, Zhang Q, Chen Z, He W, Xu J. Dracorhodin perchlorate inhibits osteoclastogenesis through repressing RANKL-stimulated NFATc1 activity. J Cell Mol Med. 2020 Mar;24(6):3303-3313. doi: 10.1111/jcmm.15003. Epub 2020 Jan 21. PMID: 31965715; PMCID: PMC7131942. 3. Xiong Z, Huo M, Jia Y, Zhou C, Ma X, Yin H, Jiang X, Yu W. Dracorhodin Perchlorate Regulates the Expression of Inflammatory Cytokines through the TLR4 Pathway and Improves Skin Wound Healing in Diabetic Rats. Evid Based Complement Alternat Med. 2022 Apr 14;2022:9050686. doi: 10.1155/2022/9050686. PMID: 35463063; PMCID: PMC9023164. 4. Liu L, Liang C, Mei P, Zhu H, Hou M, Yu C, Song Z, Bao Y, Huang Y, Yi J, Wang S, Wu Y, Zheng L, Sun Y, Wang G, Huo M, Yang S, Sun L, Li Y. Dracorhodin perchlorate protects pancreatic β-cells against glucotoxicity- or lipotoxicity-induced dysfunction and apoptosis in vitro and in vivo. FEBS J. 2019 Sep;286(18):3718-3736. doi: 10.1111/febs.15020. Epub 2019 Aug 14. PMID: 31349381.

In vitro protocol:

In vivo protocol:

1. Xiong Z, Huo M, Jia Y, Zhou C, Ma X, Yin H, Jiang X, Yu W. Dracorhodin Perchlorate Regulates the Expression of Inflammatory Cytokines through the TLR4 Pathway and Improves Skin Wound Healing in Diabetic Rats. Evid Based Complement Alternat Med. 2022 Apr 14;2022:9050686. doi: 10.1155/2022/9050686. PMID: 35463063; PMCID: PMC9023164. 2. Liu L, Liang C, Mei P, Zhu H, Hou M, Yu C, Song Z, Bao Y, Huang Y, Yi J, Wang S, Wu Y, Zheng L, Sun Y, Wang G, Huo M, Yang S, Sun L, Li Y. Dracorhodin perchlorate protects pancreatic β-cells against glucotoxicity- or lipotoxicity-induced dysfunction and apoptosis in vitro and in vivo. FEBS J. 2019 Sep;286(18):3718-3736. doi: 10.1111/febs.15020. Epub 2019 Aug 14. PMID: 31349381.

1: Chen X, Luo J, Meng L, Pan T, Zhao B, Tang ZG, Dai Y. [Retracted] Dracorhodin perchlorate induces the apoptosis of glioma cells. Oncol Rep. 2021 Jun;45(6):98. doi: 10.3892/or.2021.8049. Epub 2021 Apr 13. PMID: 33846807; PMCID: PMC8054315. 2: Lu CC, Yang JS, Chiu YJ, Tsai FJ, Hsu YM, Yin MC, Juan YN, Ho TJ, Chen HP. Dracorhodin perchlorate enhances wound healing via β-catenin, ERK/p38, and AKT signaling in human HaCaT keratinocytes. Exp Ther Med. 2021 Aug;22(2):822. doi: 10.3892/etm.2021.10254. Epub 2021 Jun 2. PMID: 34131445; PMCID: PMC8193218. 3: Wang X, Guo X, Yu R, Yue M, Li X, Liu B, Pan Z. Pharmacodynamics of Dracorhodin Perchlorate and Its Inflammation-Targeting Emulsion Gel for Wound Healing. Gels. 2022 Nov 4;8(11):712. doi: 10.3390/gels8110712. PMID: 36354620; PMCID: PMC9689536. 4: Liu Y, Wang Z, Ma C, Wei Z, Chen K, Wang C, Zhou C, Chen L, Zhang Q, Chen Z, He W, Xu J. Dracorhodin perchlorate inhibits osteoclastogenesis through repressing RANKL-stimulated NFATc1 activity. J Cell Mol Med. 2020 Mar;24(6):3303-3313. doi: 10.1111/jcmm.15003. Epub 2020 Jan 21. PMID: 31965715; PMCID: PMC7131942. 5: Rasul A, Ding C, Li X, Khan M, Yi F, Ali M, Ma T. Dracorhodin perchlorate inhibits PI3K/Akt and NF-κB activation, up-regulates the expression of p53, and enhances apoptosis. Apoptosis. 2012 Oct;17(10):1104-19. doi: 10.1007/s10495-012-0742-1. PMID: 22711363. 6: He Y, Ju W, Hao H, Liu Q, Lv L, Zeng F. Dracorhodin perchlorate suppresses proliferation and induces apoptosis in human prostate cancer cell line PC-3. J Huazhong Univ Sci Technolog Med Sci. 2011 Apr;31(2):215. doi: 10.1007/s11596-011-0255-0. Epub 2011 Apr 20. PMID: 21505988. 7: Xiong Z, Huo M, Jia Y, Zhou C, Ma X, Yin H, Jiang X, Yu W. Dracorhodin Perchlorate Regulates the Expression of Inflammatory Cytokines through the TLR4 Pathway and Improves Skin Wound Healing in Diabetic Rats. Evid Based Complement Alternat Med. 2022 Apr 14;2022:9050686. doi: 10.1155/2022/9050686. PMID: 35463063; PMCID: PMC9023164. 8: Jiang XW, Qiao L, Liu L, Zhang BQ, Wang XW, Han YW, Yu WH. Dracorhodin Perchlorate Accelerates Cutaneous Wound Healing in Wistar Rats. Evid Based Complement Alternat Med. 2017;2017:8950516. doi: 10.1155/2017/8950516. Epub 2017 Dec 3. PMID: 29333188; PMCID: PMC5733224. 9: Jiang X, Liu L, Qiao L, Zhang B, Wang X, Han Y, Yu W. Dracorhodin perchlorate regulates fibroblast proliferation to promote rat's wound healing. J Pharmacol Sci. 2018 Feb;136(2):66-72. doi: 10.1016/j.jphs.2017.12.003. Epub 2018 Feb 7. PMID: 29428295. 10: Chen X, Luo J, Meng L, Pan T, Zhao B, Tang ZG, Dai Y. Dracorhodin perchlorate induces the apoptosis of glioma cells. Oncol Rep. 2016 Apr;35(4):2364-72. doi: 10.3892/or.2016.4612. Epub 2016 Feb 4. Retraction in: Oncol Rep. 2021 Jun;45(6): PMID: 26846469. 11: Yu JH, Zheng GB, Liu CY, Zhang LY, Gao HM, Zhang YH, Dai CY, Huang L, Meng XY, Zhang WY, Yu XF. Dracorhodin perchlorate induced human breast cancer MCF-7 apoptosis through mitochondrial pathways. Int J Med Sci. 2013 Jul 7;10(9):1149-56. doi: 10.7150/ijms.6275. PMID: 23869191; PMCID: PMC3714391. 12: Liu Y, Shi D, Guo Y, Li M, Zha Y, Wang Q, Wang J. Dracorhodin Perochlorate attenuates Staphylococcus aureus USA300 virulence by decreasing α-toxin expression. World J Microbiol Biotechnol. 2017 Jan;33(1):17. doi: 10.1007/s11274-016-2129-x. Epub 2016 Nov 29. PMID: 27900629. 13: Yang LF, Liu X, Lv LL, Ma ZM, Feng XC, Ma TH. Dracorhodin perchlorate inhibits biofilm formation and virulence factors of Candida albicans. J Mycol Med. 2018 Mar;28(1):36-44. doi: 10.1016/j.mycmed.2017.12.011. Epub 2018 Feb 22. PMID: 29477784. 14: Xia M, Wang D, Wang M, Tashiro S, Onodera S, Minami M, Ikejima T. Dracorhodin perchlorate induces apoptosis via activation of caspases and generation of reactive oxygen species. J Pharmacol Sci. 2004 Jun;95(2):273-83. doi: 10.1254/jphs.fpj03102x. PMID: 15215653. 15: Xia M, Wang M, Tashiro S, Onodera S, Minami M, Ikejima T. Dracorhodin perchlorate induces A375-S2 cell apoptosis via accumulation of p53 and activation of caspases. Biol Pharm Bull. 2005 Feb;28(2):226-32. doi: 10.1248/bpb.28.226. PMID: 15684474. 16: Lu Z, Lu C, Li C, Jiao Y, Li Y, Zhang G. Dracorhodin perchlorate induces apoptosis and G2/M cell cycle arrest in human esophageal squamous cell carcinoma through inhibition of the JAK2/STAT3 and AKT/FOXO3a pathways. Mol Med Rep. 2019 Sep;20(3):2091-2100. doi: 10.3892/mmr.2019.10474. Epub 2019 Jul 8. PMID: 31322237; PMCID: PMC6691268. 17: Zhang P, Li J, Tang X, Zhang J, Liang J, Zeng G. Dracorhodin perchlorate induces apoptosis in primary fibroblasts from human skin hypertrophic scars via participation of caspase-3. Eur J Pharmacol. 2014 Apr 5;728:82-92. doi: 10.1016/j.ejphar.2014.01.068. Epub 2014 Feb 10. PMID: 24525335. 18: Liu L, Liang C, Mei P, Zhu H, Hou M, Yu C, Song Z, Bao Y, Huang Y, Yi J, Wang S, Wu Y, Zheng L, Sun Y, Wang G, Huo M, Yang S, Sun L, Li Y. Dracorhodin perchlorate protects pancreatic β-cells against glucotoxicity- or lipotoxicity- induced dysfunction and apoptosis in vitro and in vivo. FEBS J. 2019 Sep;286(18):3718-3736. doi: 10.1111/febs.15020. Epub 2019 Aug 14. PMID: 31349381. 19: Krishnaraj P, Chang Y, Ho TJ, Lu NC, Lin MD, Chen HP. In vivo pro-angiogenic effects of dracorhodin perchlorate in zebrafish embryos: A novel bioactivity evaluation platform for commercial dragon blood samples. J Food Drug Anal. 2019 Jan;27(1):259-265. doi: 10.1016/j.jfda.2018.08.005. Epub 2018 Sep 28. PMID: 30648579; PMCID: PMC9298644. 20: Zhang G, Sun M, Zhang Y, Hua P, Li X, Cui R, Zhang X. Dracorhodin perchlorate induces G1/G0 phase arrest and mitochondria- mediated apoptosis in SK-MES-1 human lung squamous carcinoma cells. Oncol Lett. 2015 Jul;10(1):240-246. doi: 10.3892/ol.2015.3212. Epub 2015 May 14. PMID: 26171006; PMCID: PMC4487096.