Hypocrellin B | CAS#123940-54-5 | causes DNA strand breakage | induces apoptosis | inhibits cell proliferation

MedKoo Cat#: 540208 | Name: Hypocrellin B

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Description:

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

Hypocrellin B are photosensitive pigments isolated from Hypocrella bambusae Sacc. Hypocrellin B causes DNA strand breakage, induces apoptosis in ovarian cancer cells, and inhibits proliferation of Staphylococcus by increasing ROS levels, and damaging cell walls.

Chemical Structure

Hypocrellin B

CAS#123940-54-5

Theoretical Analysis

MedKoo Cat#: 540208

Name: Hypocrellin B

CAS#: 123940-54-5

Chemical Formula: C30H24O9

Exact Mass: 528.1420

Molecular Weight: 528.51

Elemental Analysis: C, 68.18; H, 4.58; O, 27.24

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks
10mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Hypocrellin B;

IUPAC/Chemical Name

3-acetyl-6,11-dihydroxy-4,8,9,13-tetramethoxy-2-methyl-1H-cyclohepta[ghi]perylene-5,12-dione

InChi Key

KPGRZWCQXQUGHK-UHFFFAOYSA-N

InChi Code

InChI=1S/C30H24O9/c1-10-7-13-20-19-12(26(33)28(35)29(13)38-5)8-15(36-3)22-16(37-4)9-14(32)21(24(19)22)25-23(20)17(10)18(11(2)31)30(39-6)27(25)34/h8-9,32H,7H2,1-6H3,(H,33,35)

SMILES Code

O=C1C(OC)=C(C(C)=O)C2=C(C)CC(C3=C4C(C=C(OC)C5=C(OC)C=C(O)C(C1=C23)=C54)=C6O)=C(OC)C6=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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 528.51 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: Wang X, Luo J, Leung AW, Li Y, Zhang H, Xu C. Hypocrellin B in hepatocellular carcinoma cells: Subcellular localization and sonodynamic damage. Int J Radiat Biol. 2015 May;91(5):399-406. doi: 10.3109/09553002.2015.1001532. Epub 2015 Feb 6. PubMed PMID: 25565557. 2: Wang X, Leung AW, Hua H, Xu C, Ip M. Sonodynamic action of hypocrellin B on biofilm-producing Staphylococcus epidermidis in planktonic condition. J Acoust Soc Am. 2015 Oct;138(4):2548-53. doi: 10.1121/1.4932014. PubMed PMID: 26520337. 3: Jiang Y, Leung AW, Wang X, Zhang H, Xu C. Effect of photodynamic therapy with hypocrellin B on apoptosis, adhesion, and migration of cancer cells. Int J Radiat Biol. 2014 Jul;90(7):575-9. doi: 10.3109/09553002.2014.906765. Epub 2014 Apr 23. PubMed PMID: 24661233. 4: Wang X, Ip M, Leung AW, Wang P, Zhang H, Hua H, Xu C. Sonodynamic action of hypocrellin B on methicillin-resistant Staphylococcus aureus. Ultrasonics. 2016 Feb;65:137-44. doi: 10.1016/j.ultras.2015.10.008. Epub 2015 Oct 14. PubMed PMID: 26482395. 5: Jiang Y, Leung AW, Wang X, Zhang H, Xu C. Inactivation of Staphylococcus aureus by photodynamic action of hypocrellin B. Photodiagnosis Photodyn Ther. 2013 Dec;10(4):600-6. doi: 10.1016/j.pdpdt.2013.06.004. Epub 2013 Aug 5. PubMed PMID: 24284117. 6: Kong M, Chen Z, Yin Z, Zhang J. [Simultaneous determination of hypocrellin A, hypocrellin B, and hypocrellin C by HPLC]. Zhongguo Zhong Yao Za Zhi. 2012 Jan;37(1):75-8. Chinese. PubMed PMID: 22741466. 7: Galinato MG, Fogle RS 3rd, Galan JF. Binding interaction of hypocrellin B to myoglobin: a spectroscopic and computational study. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Nov;115:337-44. doi: 10.1016/j.saa.2013.06.052. Epub 2013 Jun 27. PubMed PMID: 23851176. 8: Zhao H, Yin R, Chen D, Ren J, Wang Y, Zhanga J, Deng H, Wang Y, Qiu H, Huang N, Zou Q, Zhao J, Gu Y. In vitro and in vivo antitumor activity of a novel hypocrellin B derivative for photodynamic therapy. Photodiagnosis Photodyn Ther. 2014 Jun;11(2):204-12. doi: 10.1016/j.pdpdt.2014.01.003. Epub 2014 Feb 14. PubMed PMID: 24534694. 9: Li T, Hou X, Deng H, Zhao J, Huang N, Zeng J, Chen H, Gu Y. Liposomal hypocrellin B as a potential photosensitizer for age-related macular degeneration: pharmacokinetics, photodynamic efficacy, and skin phototoxicity in vivo. Photochem Photobiol Sci. 2015 May;14(5):972-81. doi: 10.1039/c4pp00412d. PubMed PMID: 25793654. 10: Wang X, Leung AW, Jiang Y, Yu H, Li X, Xu C. Hypocrellin B-mediated sonodynamic action induces apoptosis of hepatocellular carcinoma cells. Ultrasonics. 2012 Apr;52(4):543-6. doi: 10.1016/j.ultras.2011.11.007. Epub 2011 Nov 28. PubMed PMID: 22172458. 11: Jiang Y, Xia X, Leung AW, Xiang J, Xu C. Apoptosis of breast cancer cells induced by hypocrellin B under light-emitting diode irradiation. Photodiagnosis Photodyn Ther. 2012 Dec;9(4):337-43. doi: 10.1016/j.pdpdt.2012.03.009. Epub 2012 May 29. PubMed PMID: 23200015. 12: Chang JE, Cho HJ, Yi E, Kim DD, Jheon S. Hypocrellin B and paclitaxel-encapsulated hyaluronic acid-ceramide nanoparticles for targeted photodynamic therapy in lung cancer. J Photochem Photobiol B. 2016 May;158:113-21. doi: 10.1016/j.jphotobiol.2016.02.035. Epub 2016 Mar 3. PubMed PMID: 26967521. 13: Zhang J, Yan H, Chen Y, Chen R, He Y, Liu W. Efficient Degradation of Aqueous Rhodamine B Irradiation Under Indoor Light Using a SiO2 -Hypocrellin B Complex. Photochem Photobiol. 2016 Jul;92(4):644-8. doi: 10.1111/php.12596. Epub 2016 Jun 6. PubMed PMID: 27135189. 14: Zhou Z, Li Q, Liu W, Zhang L, Wang X, Ma H, Sheng W, Li Z, Zeng Y, Zhong R. Photo-killing mechanism of 2-demethoxy-2,3-ethylenediamino hypocrellin B (EDAHB) to HeLa cells. J Photochem Photobiol B. 2012 Dec 5;117:47-54. doi: 10.1016/j.jphotobiol.2012.08.014. Epub 2012 Sep 15. PubMed PMID: 23037979. 15: Jia Y, Wang X, Liu Q, Leung AW, Wang P, Xu C. Sonodynamic action of hypocrellin B triggers cell apoptoisis of breast cancer cells involving caspase pathway. Ultrasonics. 2017 Jan;73:154-161. doi: 10.1016/j.ultras.2016.09.013. Epub 2016 Sep 13. PubMed PMID: 27657480. 16: Ma G, Khan SI, Jacob MR, Tekwani BL, Li Z, Pasco DS, Walker LA, Khan IA. Antimicrobial and antileishmanial activities of hypocrellins A and B. Antimicrob Agents Chemother. 2004 Nov;48(11):4450-2. PubMed PMID: 15504880; PubMed Central PMCID: PMC525422. 17: Zhou Z, Liu Y, Qin M, Sheng W, Wang X, Li Z, Zhong R. Depletion of PKM2 leads to impaired glycolysis and cell death in 2-demethoxy-2,3-ethylenediamino hypocrellin B-photoinduced A549 cells. J Photochem Photobiol B. 2014 May 5;134:1-8. doi: 10.1016/j.jphotobiol.2014.03.014. Epub 2014 Apr 2. PubMed PMID: 24792468. 18: Bai D, Xia X, Yow CM, Chu ES, Xu C. Hypocrellin B-encapsulated nanoparticle-mediated rev-caspase-3 gene transfection and photodynamic therapy on tumor cells. Eur J Pharmacol. 2011 Jan 15;650(2-3):496-500. doi: 10.1016/j.ejphar.2010.10.017. Epub 2010 Oct 21. PubMed PMID: 20970418. 19: Paramaguru G, Solomon RV, Venuvanalingam P, Renganathan R. Spectroscopic studies on TiO(2) enhanced binding of Hypocrellin B with DNA. J Fluoresc. 2011 Sep;21(5):1887-95. doi: 10.1007/s10895-011-0885-4. Epub 2011 Mar 30. PubMed PMID: 21448702. 20: Wang P, Xu CS, Xu J, Wang X, Leung AW. Hypocrellin B enhances ultrasound-induced cell death of nasopharyngeal carcinoma cells. Ultrasound Med Biol. 2010 Feb;36(2):336-42. doi: 10.1016/j.ultrasmedbio.2009.09.007. Epub 2009 Dec 16. PubMed PMID: 20018428.