Cyclam
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MedKoo CAT#: 596237

CAS#: 295-37-4

Description: Cyclam (1,4,8,11-tetraazacyclotetradecane) is an organic compound. It is a white solid that is soluble in water. The compound is notable as a macrocyclic ligand, which binds strongly to many transition metal cations. The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine.

Chemical Structure

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Cyclam
CAS# 295-37-4
Instruction

Theoretical Analysis

MedKoo Cat#: 596237
Name: Cyclam
CAS#: 295-37-4
Chemical Formula: C10H24N4
Exact Mass: 200.20
Molecular Weight: 200.330
Elemental Analysis: C, 59.96; H, 12.08; N, 27.97

Price and Availability

Size Price Availability Quantity
1g USD 250
5g USD 530
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Synonym: Cyclam; BRN 0111811; JM 1498; NSC 180811; NSC-180811; NSC180811;

IUPAC/Chemical Name: 1,4,8,11-tetraazacyclotetradecane

InChi Key: MDAXKAUIABOHTD-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2

SMILES Code: N1CCNCCCNCCNCCC1

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 200.33 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Oxley BM, Mash B, Zeller M, Banziger S, Ren T. Crystal structures of 5,12-dimethyl-1,4,8,11-tetra-aza-cyclo-tetra-decane cobalt(III) mono-phenyl-acetyl-ide and bis-phenyl-acetyl-ide. Acta Crystallogr E Crystallogr Commun. 2018 Mar 13;74(Pt 4):522-529. doi: 10.1107/S2056989018003997. eCollection 2018 Apr 1. PubMed PMID: 29765759; PubMed Central PMCID: PMC5946981.

2: Kobetić R, Ključarić V, Saftić D, Matić J, Ban Ž, Kazazić S, Žinić B. The transformation from 2°-amine to 3°-amine of cyclam ring alter the fragmentation patterns of 1-tosylcytosine-cyclam conjugates. J Mass Spectrom. 2018 May 8. doi: 10.1002/jms.4197. [Epub ahead of print] PubMed PMID: 29739033.

3: Kuehnel MF, Sahm CD, Neri G, Lee JR, Orchard KL, Cowan AJ, Reisner E. ZnSe quantum dots modified with a Ni(cyclam) catalyst for efficient visible-light driven CO(2) reduction in water. Chem Sci. 2018 Jan 24;9(9):2501-2509. doi: 10.1039/c7sc04429a. eCollection 2018 Mar 7. PubMed PMID: 29732127; PubMed Central PMCID: PMC5911736.

4: Le Bihan T, Navarro AS, Le Bris N, Le Saëc P, Gouard S, Haddad F, Gestin JF, Chérel M, Faivre-Chauvet A, Tripier R. Synthesis of C-functionalized TE1PA and comparison with its analogues. An example of bioconjugation on 9E7.4 mAb for multiple myeloma (64)Cu-PET imaging. Org Biomol Chem. 2018 Apr 27. doi: 10.1039/c8ob00499d. [Epub ahead of print] PubMed PMID: 29701218.

5: Xie Y, Wang Y, Li J, Hang Y, Oupický D. Promise of chemokine network-targeted nanoparticles in combination nucleic acid therapies of metastatic cancer. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2018 Apr 26:e1528. doi: 10.1002/wnan.1528. [Epub ahead of print] Review. PubMed PMID: 29700990.

6: Schneider CR, Manesis AC, Stevenson MJ, Shafaat HS. A photoactive semisynthetic metalloenzyme exhibits complete selectivity for CO(2) reduction in water. Chem Commun (Camb). 2018 May 3;54(37):4681-4684. doi: 10.1039/c8cc01297k. PubMed PMID: 29675518; PubMed Central PMCID: PMC5934327.

7: Drahoš B, Trávníček Z. Spin crossover Fe(ii) complexes of a cross-bridged cyclam derivative. Dalton Trans. 2018 May 1;47(17):6134-6145. doi: 10.1039/c8dt00414e. PubMed PMID: 29667691.

8: Zhanaidarova A, Moore CE, Gembicky M, Kubiak CP. Covalent attachment of [Ni(alkynyl-cyclam)](2+) catalysts to glassy carbon electrodes. Chem Commun (Camb). 2018 Apr 19;54(33):4116-4119. doi: 10.1039/c8cc00718g. PubMed PMID: 29620782.

9: Bi W, Li X, You R, Chen M, Yuan R, Huang W, Wu X, Chu W, Wu C, Xie Y. Surface Immobilization of Transition Metal Ions on Nitrogen-Doped Graphene Realizing High-Efficient and Selective CO(2) Reduction. Adv Mater. 2018 May;30(18):e1706617. doi: 10.1002/adma.201706617. Epub 2018 Mar 25. PubMed PMID: 29575274.

10: Spain M, Wong JK, Nagalingam G, Batten JM, Hortle E, Oehlers SH, Jiang XF, Murage HE, Orford JT, Crisologo P, Triccas JA, Rutledge PJ, Todd MH. Antitubercular Bis-Substituted Cyclam Derivatives: Structure-Activity Relationships and in Vivo Studies. J Med Chem. 2018 Apr 26;61(8):3595-3608. doi: 10.1021/acs.jmedchem.7b01569. Epub 2018 Apr 5. PubMed PMID: 29558124.

11: Judkins EC, Zeller M, Ren T. Synthesis and Characterizations of Macrocyclic Cr(III) and Co(III) 1-Ethynyl Naphthalene and 9-Ethynyl Anthracene Complexes: An Investigation of Structural and Spectroscopic Properties. Inorg Chem. 2018 Feb 19;57(4):2249-2259. doi: 10.1021/acs.inorgchem.7b03128. Epub 2018 Feb 7. PubMed PMID: 29411976.

12: Zhou Y, Yu F, Zhang F, Chen G, Wang K, Sun M, Li J, Oupický D. Cyclam-Modified PEI for Combined VEGF siRNA Silencing and CXCR4 Inhibition To Treat Metastatic Breast Cancer. Biomacromolecules. 2018 Feb 12;19(2):392-401. doi: 10.1021/acs.biomac.7b01487. Epub 2018 Jan 19. PubMed PMID: 29350899.

13: Zhu J, Usov PM, Xu W, Celis-Salazar PJ, Lin S, Kessinger MC, Landaverde-Alvarado C, Cai M, May AM, Slebodnick C, Zhu D, Senanayake SD, Morris AJ. A New Class of Metal-Cyclam-Based Zirconium Metal-Organic Frameworks for CO(2) Adsorption and Chemical Fixation. J Am Chem Soc. 2018 Jan 24;140(3):993-1003. doi: 10.1021/jacs.7b10643. Epub 2018 Jan 16. PubMed PMID: 29268601.

14: Haas RM, Hern Z, Sproules S, Hess CR. An Unsymmetric Ligand Framework for Noncoupled Homo- and Heterobimetallic Complexes. Inorg Chem. 2017 Dec 18;56(24):14738-14742. doi: 10.1021/acs.inorgchem.7b02294. Epub 2017 Nov 27. PubMed PMID: 29172466.

15: Huang SL, Liu N, Ling Y, Luo HK. Ir(III) -based Octahedral Metalloligands Derived Primitive Cubic Frameworks for Enhanced CO(2) /N(2) Separation. Chem Asian J. 2017 Dec 14;12(24):3110-3113. doi: 10.1002/asia.201701339. Epub 2017 Nov 14. PubMed PMID: 29057626.

16: Lau YH, Clegg JK, Price JR, Macquart RB, Todd MH, Rutledge PJ. Molecular Switches for any pH: A Systematic Study of the Versatile Coordination Behaviour of Cyclam Scorpionands. Chemistry. 2018 Feb 1;24(7):1573-1585. doi: 10.1002/chem.201703488. Epub 2017 Dec 27. PubMed PMID: 29052259.

17: Blahut J, Bernášek K, Gálisová A, Herynek V, Císařová I, Kotek J, Lang J, Matějková S, Hermann P. Paramagnetic (19)F Relaxation Enhancement in Nickel(II) Complexes of N-Trifluoroethyl Cyclam Derivatives and Cell Labeling for (19)F MRI. Inorg Chem. 2017 Nov 6;56(21):13337-13348. doi: 10.1021/acs.inorgchem.7b02119. PubMed PMID: 29048157.

18: Smolková R, Zeleňák V, Smolko L, Sabolová D, Kuchár J, Gyepes R. Novel Zn(II) complexes with non-steroidal anti-inflammatory ligand, flufenamic acid: Characterization, topoisomerase I inhibition activity, DNA and HSA binding studies. J Inorg Biochem. 2017 Dec;177:143-158. doi: 10.1016/j.jinorgbio.2017.09.005. Epub 2017 Sep 15. PubMed PMID: 28963956.

19: Munshi MU, Craig SM, Berden G, Martens J, DeBlase AF, Foreman DJ, McLuckey SA, Oomens J, Johnson MA. Preparation of Labile Ni(+)(cyclam) Cations in the Gas Phase Using Electron-Transfer Reduction through Ion-Ion Recombination in an Ion Trap and Structural Characterization with Vibrational Spectroscopy. J Phys Chem Lett. 2017 Oct 19;8(20):5047-5052. doi: 10.1021/acs.jpclett.7b02223. Epub 2017 Oct 4. PubMed PMID: 28961009; PubMed Central PMCID: PMC5677246.

20: Cabral AD, Murcar-Evans BI, Toutah K, Bancerz M, Rosa D, Yuen K, Radu TB, Ali M, Penkul A, Kraskouskaya D, Gunning PT. Structure-activity relationship study of ProxyPhos chemosensors for the detection of proximal phosphorylation and other phosphate species. Analyst. 2017 Oct 9;142(20):3922-3933. doi: 10.1039/c7an00722a. PubMed PMID: 28930308.