Tuftsin | CAS# 9063-57-4 | Immune system peptide

MedKoo Cat#: 564826 | Name: Tuftsin

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Description:

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

Tuftsin is a self-immunomodulatory molecule produced by the spleen by enzymatic cleavage of a leukophilic gamma-globulin which stimulates the phagocytic activity of blood polymorphonuclear leukocytes and neutrophils in particular. The peptide is located in the Fd fragment of the gamma-globulin molecule.

Chemical Structure

Tuftsin

CAS#9063-57-4

Theoretical Analysis

MedKoo Cat#: 564826

Name: Tuftsin

CAS#: 9063-57-4

Chemical Formula: C21H40N8O6

Exact Mass: 500.3071

Molecular Weight: 500.60

Elemental Analysis: C, 50.39; H, 8.05; N, 22.38; O, 19.18

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00
10mg	USD 625.00
25mg	USD 800.00

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Related CAS #

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Synonym

Tuftsin

IUPAC/Chemical Name

Thr-Lys-Pro-Arg; L-Threonyl-L-lysyl-L-prolyl-L-arginine

InChi Key

IESDGNYHXIOKRW-YXMSTPNBSA-N

InChi Code

InChI=1S/C21H40N8O6/c1-12(30)16(23)18(32)27-13(6-2-3-9-22)19(33)29-11-5-8-15(29)17(31)28-14(20(34)35)7-4-10-26-21(24)25/h12-16,30H,2-11,22-23H2,1H3,(H,27,32)(H,28,31)(H,34,35)(H4,24,25,26)/t12-,13+,14+,15+,16+/m1/s1

SMILES Code

N=C(N)NCCC[C@@H](C(O)=O)NC([C@H]1N(C([C@H](CCCCN)NC([C@H]([C@H](O)C)N)=O)=O)CCC1)=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

>3 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 500.60 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: Zhang L, Qiu M, Wang R, Li S, Liu X, Xu Q, Xiao L, Jiang ZX, Zhou X, Chen S. Monitoring ROS Responsive Fe3O4-based Nanoparticle Mediated Ferroptosis and Immunotherapy via 129Xe MRI. Angew Chem Int Ed Engl. 2024 May 27;63(22):e202403771. doi: 10.1002/anie.202403771. Epub 2024 Apr 23. PMID: 38551448. 2: Chapman J, Goyal A, Azevedo AM. Splenomegaly. 2023 Jun 26. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 28613657. 3: Yuan D, Zhai X, Zhu K, Ji J, Liu W. Tuftsin-tailored fusion protein inhibits the growth of circulating gastric tumor cells associated with macrophage phagocytosis. Biochem Biophys Rep. 2023 Feb 24;34:101443. doi: 10.1016/j.bbrep.2023.101443. PMID: 36875797; PMCID: PMC9974367. 4: Nakao A, Harabuchi Y, Maeda S, Tsuda K. Exploring the Quantum Chemical Energy Landscape with GNN-Guided Artificial Force. J Chem Theory Comput. 2023 Feb 14;19(3):713-717. doi: 10.1021/acs.jctc.2c01061. Epub 2023 Jan 23. PMID: 36689311; PMCID: PMC9933424. 5: Konstantinopolsky MA, Chernyakova IV, Kolik LG. Selank, a Peptide Analog of Tuftsin, Attenuates Aversive Signs of Morphine Withdrawal in Rats. Bull Exp Biol Med. 2022 Oct;173(6):730-733. doi: 10.1007/s10517-022-05624-x. Epub 2022 Nov 2. PMID: 36322304. 6: Jiang J, Wang Y, Li Y, Wang J, Zhang Y, Wang X, Wang X, Zhang H. [Preparation and immungenicity of recombinant protein containing intramolecular adjuvant in SARS-CoV-2 RBD domain]. Sheng Wu Gong Cheng Xue Bao. 2022 Sep 25;38(9):3353-3362. Chinese. doi: 10.13345/j.cjb.210883. PMID: 36151805. 7: Zou H, Li M, Li X, Zheng W, Kuang H, Wang M, Zhang W, Ran H, Ma H, Zhou X. Multimodal imaging and photothermal synergistic immunotherapy of retinoblastoma with tuftsin-loaded carbonized MOF nanoparticles. Drug Deliv. 2022 Dec;29(1):1785-1799. doi: 10.1080/10717544.2022.2081379. PMID: 35642917; PMCID: PMC9176417. 8: Huang J, Wang J, Li Y, Wang Z, Chu M, Wang Y. Tuftsin: A Natural Molecule Against SARS-CoV-2 Infection. Front Mol Biosci. 2022 Mar 23;9:859162. doi: 10.3389/fmolb.2022.859162. PMID: 35402510; PMCID: PMC8984176. 9: Wen E, Xin G, Li S, Dong Y, Zhu Y, Wan C, Yu X, Wei Z, Wang Y, Li F, Zhang K, Niu H, Huang W. Tuftsin ameliorates splenic inflammatory injury by promoting neuropilin-1 in severe acute pancreatitis. Biochem Pharmacol. 2022 May;199:115030. doi: 10.1016/j.bcp.2022.115030. Epub 2022 Apr 4. PMID: 35381211. 10: Borbála Horváth L, Krátký M, Pflégr V, Méhes E, Gyulai G, Kohut G, Babiczky Á, Biri-Kovács B, Baranyai Z, Vinšová J, Bősze S. Host cell targeting of novel antimycobacterial 4-aminosalicylic acid derivatives with tuftsin carrier peptides. Eur J Pharm Biopharm. 2022 May;174:111-130. doi: 10.1016/j.ejpb.2022.03.009. Epub 2022 Apr 2. PMID: 35378278. 11: Tanzi L, Terreni M, Zhang Y. Synthesis and biological application of glyco- and peptide derivatives of fullerene C60. Eur J Med Chem. 2022 Feb 15;230:114104. doi: 10.1016/j.ejmech.2022.114104. Epub 2022 Jan 10. PMID: 35051749. 12: Wen E, Xin G, Su W, Li S, Zhang Y, Dong Y, Yang X, Wan C, Chen Z, Yu X, Zhang K, Niu H, Huang W. Activation of TLR4 induces severe acute pancreatitis- associated spleen injury via ROS-disrupted mitophagy pathway. Mol Immunol. 2022 Feb;142:63-75. doi: 10.1016/j.molimm.2021.12.012. Epub 2021 Dec 26. PMID: 34965485. 13: Wysocka M, Dzierzbicka K, Krawczyk B. Evaluating the antibacterial activity of muramyl dipeptide derivatives, retro-tuftsin derivatives, and anthraquinone oligopeptides against a range of pathogenic bacteria. Acta Biochim Pol. 2021 Aug 30;68(3):449-455. doi: 10.18388/abp.2020_5757. PMID: 34460213. 14: Gu Y, Zhao Y, Zhang Z, Hao J, Zheng Y, Liu Q, Liu Y, Shi L. An Antibody-like Polymeric Nanoparticle Removes Intratumoral Galectin-1 to Enhance Antitumor T-Cell Responses in Cancer Immunotherapy. ACS Appl Mater Interfaces. 2021 May 19;13(19):22159-22168. doi: 10.1021/acsami.1c02116. Epub 2021 May 6. PMID: 33955217. 15: Huang X, Lu Y, Li L, Sun T, Jiang X, Li M, Zhang T, Yu A. Protective effect of acute splenic irradiation in rats with traumatic brain injury. Neuroreport. 2021 May 19;32(8):711-720. doi: 10.1097/WNR.0000000000001650. PMID: 33876783. 16: Liang DS, Wen ZJ, Wang JH, Zhu FF, Guo F, Zhou JL, Xu JJ, Zhong HJ. Legumain protease-sheddable PEGylated, tuftsin-modified nanoparticles for selective targeting to tumour-associated macrophages. J Drug Target. 2022 Jan;30(1):82-93. doi: 10.1080/1061186X.2021.1906886. Epub 2021 Nov 16. PMID: 33775195. 17: Baranyai Z, Biri-Kovács B, Krátký M, Szeder B, Debreczeni ML, Budai J, Kovács B, Horváth L, Pári E, Németh Z, Cervenak L, Zsila F, Méhes E, Kiss É, Vinšová J, Bősze S. Cellular Internalization and Inhibition Capacity of New Anti-Glioma Peptide Conjugates: Physicochemical Characterization and Evaluation on Various Monolayer- and 3D-Spheroid-Based in Vitro Platforms. J Med Chem. 2021 Mar 25;64(6):2982-3005. doi: 10.1021/acs.jmedchem.0c01399. Epub 2021 Mar 15. PMID: 33719423. 18: Murugesan K, Srinivasan P, Mahadeva R, Gupta CM, Haq W. Tuftsin-Bearing Liposomes Co-Encapsulated with Doxorubicin and Curcumin Efficiently Inhibit EAC Tumor Growth in Mice. Int J Nanomedicine. 2020 Dec 31;15:10547-10559. doi: 10.2147/IJN.S276336. PMID: 33414637; PMCID: PMC7783201. 19: Khan MA. Targeted Drug Delivery Using Tuftsin-bearing Liposomes: Implications in the Treatment of Infectious Diseases and Tumors. Curr Drug Targets. 2021;22(7):770-778. doi: 10.2174/1389450121999201125200756. PMID: 33243117. 20: Peng H, Wang JH, Guo F, Zhu FF, Wen ZJ, Zhong HJ, Liang DS. Legumain protease-activated tuftsin-functionalized nanoparticles for dual-targeting TAMs and cancer chemotherapy. Colloids Surf B Biointerfaces. 2021 Jan;197:111442. doi: 10.1016/j.colsurfb.2020.111442. Epub 2020 Nov 2. PMID: 33166937.