Cytochalasin D | CAS#22144-77-0 | fungal metabolite

MedKoo Cat#: 561880 | Name: Cytochalasin D

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Description:

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

Cytochalasin D is a fungal metabolite. It blocks formation of contractile microfilament structures, resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. It also inhibits actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.

Chemical Structure

Cytochalasin D

CAS#22144-77-0

Theoretical Analysis

MedKoo Cat#: 561880

Name: Cytochalasin D

CAS#: 22144-77-0

Chemical Formula: C30H37NO6

Exact Mass: 507.2621

Molecular Weight: 507.62

Elemental Analysis: C, 70.98; H, 7.35; N, 2.76; O, 18.91

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 250.00	Back order
5mg	USD 650.00	Back order

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Synonym

Cytochalasin D; Zygosporin A; Lygosporin A; NSC 209835; NSC209835; NSC-209835;

IUPAC/Chemical Name

(3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-3-Benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1H-cycloundeca[d]isoindol-15-yl acetate

InChi Key

SDZRWUKZFQQKKV-JHADDHBZSA-N

InChi Code

InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1

SMILES Code

CC(O[C@@H]([C@@]1([C@](/C=C/C[C@@H]2C)([H])[C@@H]3O)C(N[C@@H](CC4=CC=CC=C4)[C@]1([H])[C@H](C)C3=C)=O)/C=C/[C@@](C)(O)C2=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

>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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Cytochalasin D (Zygosporin A; NSC 209835) is an inhibitor of actin polymerization derived from fungus, inhibits the G-actin–cofilin interaction by binding to G-actin.

In vitro activity:

The osteogenic differentiation of MC3T3-E1 cells induced by Cyto D (cytochalasin D) was assessed by alkaline phosphatase (ALP) staining, Alizarin Red S (ARS) staining, western blotting and quantitative real-time polymerase chain reaction (RT-qPCR). The results showed that the optimized concentration of action was 10-2µg/ml. The expression of Runx2, OCN and OSX was up-regulated by the supplement of Cyto D. Reference: Curr Mol Med. 2019;20(1):79-88. https://pubmed.ncbi.nlm.nih.gov/31589123/

In vivo activity:

Relative to the DMSO-treated control group, significant lung metastatic colonies were observed on the lung surfaces of the mice treated with CytD (cytochalasin D) (Fig. 1A). The average lung weight of the CytD-treated mice was significantly greater than that of the DMSO-treated mice, 1.46±0.15 vs. 0.82±0.18 g (Fig. 1B) (P<0.001). In addition, the number of surface metastatic colonies was also significantly increased in CytD-treated mice relative to controls, 893.47±135.69 vs. 294.63±143.29 (Fig. 1C) (P<0.001). Reference: Oncol Rep. 2013 Jul;30(1):478-84. https://pubmed.ncbi.nlm.nih.gov/23615686/

	Solvent	mg/mL	mM
Solubility
	DMSO	75.0	147.75
	Ethanol	5.0	9.85

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 507.62 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. Liu Q, Zhuang Y, Ouyang N, Yu H. Cytochalasin D Promotes Osteogenic Differentiation of MC3T3-E1 Cells via p38-MAPK Signaling Pathway. Curr Mol Med. 2019;20(1):79-88. doi: 10.2174/1566524019666191007104816. PMID: 31589123. 2. Gao M, Wu S, Ji J, Zhang J, Liu Q, Yue Y, Liu L, Liu X, Liu W. The influence of actin depolymerization induced by Cytochalasin D and mechanical stretch on interleukin-8 expression and JNK phosphorylation levels in human retinal pigment epithelial cells. BMC Ophthalmol. 2017 Apr 7;17(1):43. doi: 10.1186/s12886-017-0437-z. PMID: 28388885; PMCID: PMC5384187. 3. Huang FY, Mei WL, Tan GH, Dai HF, Li YN, Guo JL, Huang YH, Zhao HG, Wang H, Zhou SL, Lin YY. Cytochalasin D promotes pulmonary metastasis of B16 melanoma through expression of tissue factor. Oncol Rep. 2013 Jul;30(1):478-84. doi: 10.3892/or.2013.2423. Epub 2013 Apr 24. PMID: 23615686. 4. Huang FY, Li YN, Mei WL, Dai HF, Zhou P, Tan GH. Cytochalasin D, a tropical fungal metabolite, inhibits CT26 tumor growth and angiogenesis. Asian Pac J Trop Med. 2012 Mar;5(3):169-74. doi: 10.1016/S1995-7645(12)60019-4. PMID: 22305779.

In vitro protocol:

In vivo protocol:

1. Huang FY, Mei WL, Tan GH, Dai HF, Li YN, Guo JL, Huang YH, Zhao HG, Wang H, Zhou SL, Lin YY. Cytochalasin D promotes pulmonary metastasis of B16 melanoma through expression of tissue factor. Oncol Rep. 2013 Jul;30(1):478-84. doi: 10.3892/or.2013.2423. Epub 2013 Apr 24. PMID: 23615686. 2. Huang FY, Li YN, Mei WL, Dai HF, Zhou P, Tan GH. Cytochalasin D, a tropical fungal metabolite, inhibits CT26 tumor growth and angiogenesis. Asian Pac J Trop Med. 2012 Mar;5(3):169-74. doi: 10.1016/S1995-7645(12)60019-4. PMID: 22305779.

1: Erdoes G, Reid C, Koster A. The Dark Side of FIBTEM: Cytochalasin D. J Cardiothorac Vasc Anesth. 2020 Jun;34(6):1474-1475. doi: 10.1053/j.jvca.2020.01.029. Epub 2020 Jan 22. PMID: 32144067. 2: Liu Q, Zhuang Y, Ouyang N, Yu H. Cytochalasin D Promotes Osteogenic Differentiation of MC3T3-E1 Cells via p38-MAPK Signaling Pathway. Curr Mol Med. 2019;20(1):79-88. doi: 10.2174/1566524019666191007104816. PMID: 31589123. 3: Martinez G, Cappetta D, Telesca M, Urbanek K, Castaldo G, Dhellemmes M, Mele VG, Chioccarelli T, Porreca V, Barbotin AL, Boursier A, Guillou F, Coutton C, Brouillet S, De Angelis A, Berrino L, Pierantoni R, Cobellis G, Chianese R, Manfrevola F. Cytochalasin D restores nuclear size acting on F-actin and IZUMO1 localization in low-quality spermatozoa. Int J Biol Sci. 2023 Apr 17;19(7):2234-2255. doi: 10.7150/ijbs.77166. PMID: 37151878; PMCID: PMC10158014. 4: Huang FY, Li YN, Mei WL, Dai HF, Zhou P, Tan GH. Cytochalasin D, a tropical fungal metabolite, inhibits CT26 tumor growth and angiogenesis. Asian Pac J Trop Med. 2012 Mar;5(3):169-74. doi: 10.1016/S1995-7645(12)60019-4. PMID: 22305779. 5: Chiang RK, Yao XY, Takeuchi A, Dalal R, Marmor MF. Cytochalasin D reversibly weakens retinal adhesiveness. Curr Eye Res. 1995 Dec;14(12):1109-13. doi: 10.3109/02713689508995817. PMID: 8974840. 6: Xu H, Fang WS, Chen XG, He WY, Cheng KD. Cytochalasin D from Hypocrella bambusae. J Asian Nat Prod Res. 2001;3(2):151-5. doi: 10.1080/10286020108041383. PMID: 11407815. 7: Shoji K, Ohashi K, Sampei K, Oikawa M, Mizuno K. Cytochalasin D acts as an inhibitor of the actin-cofilin interaction. Biochem Biophys Res Commun. 2012 Jul 20;424(1):52-7. doi: 10.1016/j.bbrc.2012.06.063. Epub 2012 Jun 20. PMID: 22728040. 8: Calaghan SC, White E, Bedut S, Le Guennec JY. Cytochalasin D reduces Ca2+ sensitivity and maximum tension via interactions with myofilaments in skinned rat cardiac myocytes. J Physiol. 2000 Dec 1;529 Pt 2(Pt 2):405-11. doi: 10.1111/j.1469-7793.2000.00405.x. PMID: 11101650; PMCID: PMC2270202. 9: Leatherwood WH, Bortner BA, Draeger RW, Dahners LE, Rubin J, Weinhold PS. Evaluation of zoledronate, cytochalasin-D, and desferrioxamine on osseointegration in an intra-medullary femoral implant model. J Musculoskelet Neuronal Interact. 2020 Mar 3;20(1):121-127. PMID: 32131376; PMCID: PMC7104579. 10: Sauman I, Berry SJ. Cytochalasin-D treatment triggers premature apoptosis of insect ovarian follicle and nurse cells. Int J Dev Biol. 1993 Sep;37(3):441-50. PMID: 8292538. 11: Huang FY, Mei WL, Li YN, Tan GH, Dai HF, Guo JL, Wang H, Huang YH, Zhao HG, Zhou SL, Li L, Lin YY. The antitumour activities induced by pegylated liposomal cytochalasin D in murine models. Eur J Cancer. 2012 Sep;48(14):2260-9. doi: 10.1016/j.ejca.2011.12.018. Epub 2012 Jan 16. PMID: 22257793. 12: Kim M, Song K, Jin EJ, Sonn J. Staurosporine and cytochalasin D induce chondrogenesis by regulation of actin dynamics in different way. Exp Mol Med. 2012 Sep 30;44(9):521-8. doi: 10.3858/emm.2012.44.9.059. PMID: 22684244; PMCID: PMC3465745. 13: Makioka A, Kumagai M, Ohtomo H, Kobayashi S, Takeuchi T. Effect of cytochalasin D on the growth, encystation, and multinucleation of Entamoeba invadens. Parasitol Res. 2000 Jul;86(7):599-602. doi: 10.1007/pl00008536. PMID: 10935912. 14: Shin HY, Lee EH, Shin TY, Kim HM. Effect of cytochalasin D on systemic and local anaphylaxis in a murine model. Pharmacol Res. 1997 Aug;36(2):141-6. doi: 10.1006/phrs.1997.0218. PMID: 9344643. 15: Undrovinas AI, Maltsev VA. Cytochalasin D alters kinetics of Ca2+ transient in rat ventricular cardiomyocytes: an effect of altered actin cytoskeleton? J Mol Cell Cardiol. 1998 Aug;30(8):1665-70. doi: 10.1006/jmcc.1998.0715. PMID: 9737950. 16: Lang T, Toller W, Gütl M, Mahla E, Metzler H, Rehak P, März W, Halwachs- Baumann G. Different effects of abciximab and cytochalasin D on clot strength in thrombelastography. J Thromb Haemost. 2004 Jan;2(1):147-53. doi: 10.1111/j.1538-7836.2004.00555.x. PMID: 14717978. 17: Salu KJ, Bosmans JM, Huang Y, Hendriks M, Verhoeven M, Levels A, Cooper S, De Scheerder IK, Vrints CJ, Bult H. Effects of cytochalasin D-eluting stents on intimal hyperplasia in a porcine coronary artery model. Cardiovasc Res. 2006 Feb 1;69(2):536-44. doi: 10.1016/j.cardiores.2005.11.012. Epub 2005 Dec 28. PMID: 16386237. 18: Berg A, Rubin K, Reed RK. Cytochalasin D induces edema formation and lowering of interstitial fluid pressure in rat dermis. Am J Physiol Heart Circ Physiol. 2001 Jul;281(1):H7-13. doi: 10.1152/ajpheart.2001.281.1.H7. PMID: 11406462. 19: Hayduk EJ, Lee KH. Cytochalasin D can improve heterologous protein productivity in adherent Chinese hamster ovary cells. Biotechnol Bioeng. 2005 May 5;90(3):354-64. doi: 10.1002/bit.20438. PMID: 15772946. 20: Stevenson BR, Begg DA. Concentration-dependent effects of cytochalasin D on tight junctions and actin filaments in MDCK epithelial cells. J Cell Sci. 1994 Mar;107 ( Pt 3):367-75. doi: 10.1242/jcs.107.3.367. PMID: 8006058.