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MedKoo Cat#: 112180 | Name: Erbstatin analog
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Description:

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

Erbstatin is a potent, small-molecule inhibitor of EGF receptor-associated tyrosine kinase which could potentially be a therapeutic agent to prevent malignant growth.

Chemical Structure

Erbstatin analog
Erbstatin analog
CAS#63177-57-1

Theoretical Analysis

MedKoo Cat#: 112180

Name: Erbstatin analog

CAS#: 63177-57-1

Chemical Formula: C10H10O4

Exact Mass: 194.0579

Molecular Weight: 194.19

Elemental Analysis: C, 61.85; H, 5.19; O, 32.96

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 850.00 2 Weeks
100mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Erbstatin analog; Methyl 2,5-dihydoxycinnamate
IUPAC/Chemical Name
methyl (Z)-3-(2,5-dihydroxyphenyl)acrylate
InChi Key
BQCNSTFWSKOWMA-DJWKRKHSSA-N
InChi Code
InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2-
SMILES Code
O=C(OC)/C=C\C1=CC(O)=CC=C1O
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
Solvent mg/mL mM
Solubility
Ethanol 10.0 51.49
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 194.19 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: Kawada M, Tawara J, Tsuji T, Honma Y, Hozumi M, Wang JY, Umezawa K. Inhibition of Abelson oncogene function by erbstatin analogues. Drugs Exp Clin Res. 1993;19(6):235-41. PMID: 8013266. 2: Toi M, Mukaida H, Wada T, Hirabayashi N, Toge T, Hori T, Umezawa K. Antineoplastic effect of erbstatin on human mammary and esophageal tumors in athymic nude mice. Eur J Cancer. 1990;26(6):722-4. doi: 10.1016/0277-5379(90)90126-e. PMID: 2144161. 3: Takekura N, Yasui W, Kyo E, Yoshida K, Kameda T, Kitadai Y, Abe K, Umezawa K, Tahara E. Effects of tyrosine kinase inhibitor, erbstatin, on cell growth and growth-factor/receptor gene expression in human gastric carcinoma cells. Int J Cancer. 1991 Apr 1;47(6):938-42. doi: 10.1002/ijc.2910470626. PMID: 1849125. 4: Sugata D, Yamashita K, Umezawa K. Inhibition of serum-induced M-phase progression by a tyrosine kinase inhibitor, erbstatin. Biochem Biophys Res Commun. 1993 Jul 15;194(1):239-45. doi: 10.1006/bbrc.1993.1810. PMID: 8333839. 5: McIntyre BS, Sylvester PW. Genistein and erbstatin inhibition of normal mammary epithelial cell proliferation is associated with EGF-receptor down- regulation. Cell Prolif. 1998 Feb;31(1):35-46. doi: 10.1046/j.1365-2184.1998.00108.x. PMID: 9666817; PMCID: PMC6495388. 6: Kryukova Y, Rybin VO, Qu J, Steinberg SF, Robinson RB. Age-dependent differences in the inhibition of HCN2 current in rat ventricular myocytes by the tyrosine kinase inhibitor erbstatin. Pflugers Arch. 2009 Feb;457(4):821-30. doi: 10.1007/s00424-008-0565-7. Epub 2008 Aug 12. PMID: 18696104; PMCID: PMC2701652. 7: Imoto M, Umezawa K, Komuro K, Sawa T, Takeuchi T, Umezawa H. Antitumor activity of erbstatin, a tyrosine protein kinase inhibitor. Jpn J Cancer Res. 1987 Apr;78(4):329-32. PMID: 3108212. 8: Markovits J, Larsen AK, Ségal-Bendirdjian E, Fossé P, Saucier JM, Gazit A, Levitzki A, Umezawa K, Jacquemin-Sablon A. Inhibition of DNA topoisomerases I and II and induction of apoptosis by erbstatin and tyrphostin derivatives. Biochem Pharmacol. 1994 Aug 3;48(3):549-60. doi: 10.1016/0006-2952(94)90285-2. PMID: 8068042. 9: Stanwell C, Burke TR Jr, Yuspa SH. The erbstatin analogue methyl 2,5-dihydroxycinnamate cross-links proteins and is cytotoxic to normal and neoplastic epithelial cells by a mechanism independent of tyrosine kinase inhibition. Cancer Res. 1995 Nov 1;55(21):4950-6. PMID: 7585535. 10: Zhang ZH, Rhodes KJ, Childers WE, Argentieri TM, Wang Q. Disinactivation of N-type inactivation of voltage-gated K channels by an erbstatin analogue. J Biol Chem. 2004 Jul 9;279(28):29226-30. doi: 10.1074/jbc.M403290200. Epub 2004 May 10. PMID: 15136567. 11: Simizu S, Imoto M, Masuda N, Takada M, Umezawa K. Involvement of hydrogen peroxide production in erbstatin-induced apoptosis in human small cell lung carcinoma cells. Cancer Res. 1996 Nov 1;56(21):4978-82. PMID: 8895753. 12: Daya-Makin M, Pelech SL, Levitzki A, Hudson AT. Erbstatin and tyrphostins block protein-serine kinase activation and meiotic maturation of sea star oocytes. Biochim Biophys Acta. 1991 Jun 7;1093(1):87-94. doi: 10.1016/0167-4889(91)90142-k. PMID: 1828701. 13: Salari H, Duronio V, Howard SL, Demos M, Jones K, Reany A, Hudson AT, Pelech SL. Erbstatin blocks platelet activating factor-induced protein-tyrosine phosphorylation, polyphosphoinositide hydrolysis, protein kinase C activation, serotonin secretion and aggregation of rabbit platelets. FEBS Lett. 1990 Apr 9;263(1):104-8. doi: 10.1016/0014-5793(90)80715-u. PMID: 1691984. 14: Stanwell C, Ye B, Yuspa SH, Burke TR Jr. Cell protein cross-linking by erbstatin and related compounds. Biochem Pharmacol. 1996 Aug 9;52(3):475-80. doi: 10.1016/0006-2952(96)00250-x. PMID: 8687502. 15: Naccache PH, Gilbert C, Caon AC, Gaudry M, Huang CK, Bonak VA, Umezawa K, McColl SR. Selective inhibition of human neutrophil functional responsiveness by erbstatin, an inhibitor of tyrosine protein kinase. Blood. 1990 Nov 15;76(10):2098-104. PMID: 2173635. 16: Imoto M, Umezawa K, Sawa T, Takeuchi T, Umezawa H. In situ inhibition of tyrosine protein kinase by erbstatin. Biochem Int. 1987 Nov;15(5):989-95. PMID: 3501720. 17: Umezawa H, Imoto M, Sawa T, Isshiki K, Matsuda N, Uchida T, Iinuma H, Hamada M, Takeuchi T. Studies on a new epidermal growth factor-receptor kinase inhibitor, erbstatin, produced by MH435-hF3. J Antibiot (Tokyo). 1986 Jan;39(1):170-3. doi: 10.7164/antibiotics.39.170. PMID: 3005217. 18: Bishop WR, Petrin J, Wang L, Ramesh U, Doll RJ. Inhibition of protein kinase C by the tyrosine kinase inhibitor erbstatin. Biochem Pharmacol. 1990 Nov 1;40(9):2129-35. doi: 10.1016/0006-2952(90)90245-g. PMID: 2242040. 19: Hsu CY, Jacoski MV, Maguire MP, Spada AP, Zilberstein A. Inhibition kinetics and selectivity of the tyrosine kinase inhibitor erbstatin and a pyridone-based analogue. Biochem Pharmacol. 1992 Jun 9;43(11):2471-7. doi: 10.1016/0006-2952(92)90327-f. PMID: 1319162. 20: Oikawa T, Ashino H, Shimamura M, Hasegawa M, Morita I, Murota S, Ishizuka M, Takeuchi T. Inhibition of angiogenesis by erbstatin, an inhibitor of tyrosine kinase. J Antibiot (Tokyo). 1993 May;46(5):785-90. doi: 10.7164/antibiotics.46.785. PMID: 7685752.