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MedKoo Cat#: 581102 | Name: Cylindrin

Description:

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

Cylindrin is a six-stranded antiparallel beta barrel obtained from amyloidogenic strands of crystallin. It induces cell toxicity through an unknown mechanism.

Chemical Structure

Cylindrin
Cylindrin
CAS#17904-55-1

Theoretical Analysis

MedKoo Cat#: 581102

Name: Cylindrin

CAS#: 17904-55-1

Chemical Formula: C31H52O

Exact Mass: 440.4018

Molecular Weight: 440.75

Elemental Analysis: C, 84.48; H, 11.89; O, 3.63

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cylindrin; Hollow cylinder protein complex;
IUPAC/Chemical Name
(3S,3aS,5aS,5bS,7aR,9S,11aR,13aR,13bS)-3-isopropyl-9-methoxy-3a,5a,8,8,11a,13a-hexamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene
InChi Key
MRNPHCMRIQYRFU-MPVKEFPDSA-N
InChi Code
InChI=1S/C31H52O/c1-20(2)21-10-13-25-29(21,6)18-19-30(7)23-11-12-24-27(3,4)26(32-9)15-16-28(24,5)22(23)14-17-31(25,30)8/h14,20-21,23-26H,10-13,15-19H2,1-9H3/t21-,23+,24-,25-,26-,28-,29-,30-,31+/m0/s1
SMILES Code
CO[C@H](C(C)(C)[C@@H]1CC[C@H]2[C@@]3(CC[C@]4(C)[C@@H]5CC[C@H]4C(C)C)C)CC[C@@]1(C)C2=CC[C@@]35C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 440.75 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.

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: Zulpo M, Kotulska M. Comparative modeling of hypothetical amyloid pores based on cylindrin. J Mol Model. 2015 Jun;21(6):151. doi: 10.1007/s00894-015-2691-4. Epub 2015 May 21. PubMed PMID: 25994458. 2: Harris JR, Naeem I. Further studies on the characterization of cylindrin and torin, two extrinsic proteins of the erythrocyte membrane. Biochim Biophys Acta. 1981 Sep 29;670(2):285-90. PubMed PMID: 6895329. 3: Berhanu WM, Hansmann UH. The stability of cylindrin β-barrel amyloid oligomer models-a molecular dynamics study. Proteins. 2013 Sep;81(9):1542-55. doi: 10.1002/prot.24302. Epub 2013 Jun 22. PubMed PMID: 23606599; PubMed Central PMCID: PMC4206217. 4: Harris JR. Torin and cylindrin, two extrinsic proteins of the erythrocyte membrane: a review. Nouv Rev Fr Hematol. 1980;22(4):411-48. PubMed PMID: 6166920. 5: Lande WM, Thiemann PV, Fisher KA, Mentzer WC. Two-dimensional electrophoretic analysis of human erythrocyte cylindrin. Biochim Biophys Acta. 1984 Nov 21;778(1):105-11. PubMed PMID: 6548644. 6: Laganowsky A, Liu C, Sawaya MR, Whitelegge JP, Park J, Zhao M, Pensalfini A, Soriaga AB, Landau M, Teng PK, Cascio D, Glabe C, Eisenberg D. Atomic view of a toxic amyloid small oligomer. Science. 2012 Mar 9;335(6073):1228-31. doi: 10.1126/science.1213151. PubMed PMID: 22403391; PubMed Central PMCID: PMC3959867. 7: Harris JR. Erythrocyte cylindrin: possible identity with the ubiquitous 20S high molecular weight protease complex and the prosome particle. Indian J Biochem Biophys. 1988 Dec;25(6):459-66. Review. PubMed PMID: 3076577. 8: Do TD, LaPointe NE, Nelson R, Krotee P, Hayden EY, Ulrich B, Quan S, Feinstein SC, Teplow DB, Eisenberg D, Shea JE, Bowers MT. Amyloid β-Protein C-Terminal Fragments: Formation of Cylindrins and β-Barrels. J Am Chem Soc. 2016 Jan 20;138(2):549-57. doi: 10.1021/jacs.5b09536. Epub 2016 Jan 6. PubMed PMID: 26700445; PubMed Central PMCID: PMC4741107. 9: Liu X, Zhang B, Chou G, Yang L, Wang Z. [Chemical constituents from Imperata cylindrica]. Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(15):2296-300. Chinese. PubMed PMID: 23189737. 10: Zheng W, Tsai MY, Chen M, Wolynes PG. Exploring the aggregation free energy landscape of the amyloid-β protein (1-40). Proc Natl Acad Sci U S A. 2016 Oct 18;113(42):11835-11840. Epub 2016 Oct 3. PubMed PMID: 27698130; PubMed Central PMCID: PMC5081630. 11: Liu C, Zhao M, Jiang L, Cheng PN, Park J, Sawaya MR, Pensalfini A, Gou D, Berk AJ, Glabe CG, Nowick J, Eisenberg D. Out-of-register β-sheets suggest a pathway to toxic amyloid aggregates. Proc Natl Acad Sci U S A. 2012 Dec 18;109(51):20913-8. doi: 10.1073/pnas.1218792109. Epub 2012 Dec 3. PubMed PMID: 23213214; PubMed Central PMCID: PMC3529048. 12: Ranieri G, Mazzei R, Wu Z, Li K, Giorno L. Use of a Ceramic Membrane to Improve the Performance of Two-Separate-Phase Biocatalytic Membrane Reactor. Molecules. 2016 Mar 14;21(3):345. doi: 10.3390/molecules21030345. PubMed PMID: 26985887. 13: Harris JR. Biochemical and ultrastructural characterization of a high molecular weight soluble Mg2+ -ATPase from human erythrocytes. J Mol Biol. 1984 Apr 25;174(4):705-21. PubMed PMID: 6144798. 14: Moshe A, Landau M, Eisenberg D. Preparation of Crystalline Samples of Amyloid Fibrils and Oligomers. Methods Mol Biol. 2016;1345:201-10. doi: 10.1007/978-1-4939-2978-8_13. PubMed PMID: 26453214. 15: Zhang H, Xi W, Hansmann UHE, Wei Y. Fibril-Barrel Transitions in Cylindrin Amyloids. J Chem Theory Comput. 2017 Aug 8;13(8):3936-3944. doi: 10.1021/acs.jctc.7b00383. Epub 2017 Jul 17. PubMed PMID: 28671829. 16: Wu C, Shea JE. Structural similarities and differences between amyloidogenic and non-amyloidogenic islet amyloid polypeptide (IAPP) sequences and implications for the dual physiological and pathological activities of these peptides. PLoS Comput Biol. 2013;9(8):e1003211. doi: 10.1371/journal.pcbi.1003211. Epub 2013 Aug 29. PubMed PMID: 24009497; PubMed Central PMCID: PMC3757079. 17: Fu LN, Chen LY, Liu RH, Chen DF. [Chemical constituents of rhizoma imperatae and their anti-complementary activity]. Zhong Yao Cai. 2010 Dec;33(12):1871-4. Chinese. PubMed PMID: 21548362. 18: Malech HL, Marchesi VT. Hollow cylinder protein in the cytoplasm of human erythrocytes. Biochim Biophys Acta. 1981 Oct 28;670(3):385-92. PubMed PMID: 6895331. 19: Hayward S, Milner-White EJ. Geometrical principles of homomeric β-barrels and β-helices: Application to modeling amyloid protofilaments. Proteins. 2017 Oct;85(10):1866-1881. doi: 10.1002/prot.25341. Epub 2017 Jul 12. PubMed PMID: 28646497. 20: Xi W, Vanderford EK, Hansmann UHE. Out-of-Register Aβ(42) Assemblies as Models for Neurotoxic Oligomers and Fibrils. J Chem Theory Comput. 2018 Feb 13;14(2):1099-1110. doi: 10.1021/acs.jctc.7b01106. Epub 2018 Jan 31. PubMed PMID: 29357242; PubMed Central PMCID: PMC5821112.

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