IR 783 | CAS#115970-66-6 | Heptamethine cyanine fluorescent probe

MedKoo Cat#: 463884 | Name: IR 783

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Description:

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

IR 783 is a heptamethine cyanine fluorescent probe for in vivo imaging of tumor cells. It displays excitation/emission maxima of 633/780 nm, respectively. IR 783 is transported into tumor cells, an effect that can be blocked by the organic anion transporting polypeptide (OATP) inhibitor sulfobromophthalein. In vivo, IR 783 preferentially accumulates in tumor tissue in an ACHN kidney cancer mouse xenograft model.2 It has been conjugated to polyethylenimines for tumor-specific gene delivery.

Chemical Structure

IR 783

CAS#115970-66-6 (sodium salt)

Theoretical Analysis

MedKoo Cat#: 463884

Name: IR 783

CAS#: 115970-66-6 (sodium salt)

Chemical Formula: C38H46ClN2NaO6S2

Exact Mass:

Molecular Weight: 749.35

Elemental Analysis: C, 60.91; H, 6.19; Cl, 4.73; N, 3.74; Na, 3.07; O, 12.81; S, 8.56

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 1,050.00	2 Weeks

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Related CAS #

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Synonym

IR 783; IR-783; IR783;

IUPAC/Chemical Name

sodium 4-((Z)-2-((E)-2-(2-chloro-3-((E)-2-(3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium-2-yl)vinyl)cyclohex-2-en-1-ylidene)ethylidene)-3,3-dimethylindolin-1-yl)butane-1-sulfonate

InChi Key

QQIQAVJARACLHE-UHFFFAOYSA-M

InChi Code

InChI=1S/C38H47ClN2O6S2.Na/c1-37(2)30-16-5-7-18-32(30)40(24-9-11-26-48(42,43)44)34(37)22-20-28-14-13-15-29(36(28)39)21-23-35-38(3,4)31-17-6-8-19-33(31)41(35)25-10-12-27-49(45,46)47;/h5-8,16-23H,9-15,24-27H2,1-4H3,(H-,42,43,44,45,46,47);/q;+1/p-1

SMILES Code

ClC1=C(/C=C/C2=[N+](C3=CC=CC=C3C2(C)C)CCCCS([O-])(=O)=O)CCC/C1=C\C=C4C(C)(C5=CC=CC=C5N\4CCCCS([O-])(=O)=O)C.[Na+]

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 749.35 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

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A Multimodal Ca(II) Responsive Near IR-MR Contrast Agent Exhibiting High Cellular Uptake. ACS Chem Biol. 2020 Feb 21;15(2):334-341. doi: 10.1021/acschembio.9b00638. Epub 2020 Jan 30. PMID: 31967770. 5: Duan L, Wang L, Zhang C, Yu L, Guo F, Sun Z, Xu Y, Yan F. Role of near- infrared heptamethine cyanine dye IR-783 in diagnosis of cervical cancer and its mechanism. Int J Clin Exp Pathol. 2019 Jun 1;12(6):2353-2362. PMID: 31934062; PMCID: PMC6949655. 6: Guan Y, Zhang Y, Zou J, Huang LP, Chordia MD, Yue W, Wu JJ, Pan DF. Synthesis and Biological Evaluation of Genistein-IR783 Conjugate: Cancer Cell Targeted Delivery in MCF-7 for Superior Anti-Cancer Therapy. Molecules. 2019 Nov 14;24(22):4120. doi: 10.3390/molecules24224120. PMID: 31739548; PMCID: PMC6891397. 7: Herring B, Whitt J, Aweda T, Ou J, Guenter R, Lapi S, Berry J, Chen H, Liu X, Rose JB, Jaskula-Sztul R. A growth model of neuroendocrine tumor surrogates and the efficacy of a novel somatostatin-receptor-guided antibody-drug conjugate: Perspectives on clinical response? Surgery. 2020 Jan;167(1):197-203. doi: 10.1016/j.surg.2019.04.073. Epub 2019 Sep 19. PMID: 31543319. 8: Li P, Liu Y, Liu W, Li G, Tang Q, Zhang Q, Leng F, Sheng F, Hu C, Lai W, Liu Y, Zhou M, Huang J, Zhou H, Zhang R, Zhao Y. IR-783 inhibits breast cancer cell proliferation and migration by inducing mitochondrial fission. Int J Oncol. 2019 Aug;55(2):415-424. doi: 10.3892/ijo.2019.4821. Epub 2019 Jun 6. PMID: 31173174; PMCID: PMC6615916. 9: Kwak EA, Kydd L, Lim B, Jaworski J. IR-783 Labeling of a Peptide Receptor for 'Turn-On' Fluorescence Based Sensing. Chemosensors (Basel). 2018 Dec;6(4):47. doi: 10.3390/chemosensors6040047. Epub 2018 Oct 16. PMID: 31080779; PMCID: PMC6510487. 10: Canovas C, Bellaye PS, Moreau M, Romieu A, Denat F, Goncalves V. Site- specific near-infrared fluorescent labelling of proteins on cysteine residues with meso-chloro-substituted heptamethine cyanine dyes. Org Biomol Chem. 2018 Nov 21;16(45):8831-8836. doi: 10.1039/c8ob02646g. PMID: 30411777. 11: Tang Q, Liu W, Zhang Q, Huang J, Hu C, Liu Y, Wang Q, Zhou M, Lai W, Sheng F, Li G, Zhang R. Dynamin-related protein 1-mediated mitochondrial fission contributes to IR-783-induced apoptosis in human breast cancer cells. J Cell Mol Med. 2018 Sep;22(9):4474-4485. doi: 10.1111/jcmm.13749. Epub 2018 Jul 11. PMID: 29993201; PMCID: PMC6111821. 12: De Los Reyes-Berbel E, Salto-Gonzalez R, Ortega-Muñoz M, Reche-Perez FJ, Jodar-Reyes AB, Hernandez-Mateo F, Giron-Gonzalez MD, Santoyo-Gonzalez F. PEI- NIR Heptamethine Cyanine Nanotheranostics for Tumor Targeted Gene Delivery. Bioconjug Chem. 2018 Aug 15;29(8):2561-2575. doi: 10.1021/acs.bioconjchem.8b00262. Epub 2018 Aug 6. PMID: 29953208. 13: Lv W, Shen Y, Yang H, Yang R, Cai W, Zhang J, Yuan L, Duan Y, Zhang L. A Novel Bimodal Imaging Agent Targeting HER2 Molecule of Breast Cancer. J Immunol Res. 2018 Mar 6;2018:6202876. doi: 10.1155/2018/6202876. PMID: 29854844; PMCID: PMC5944285. 14: Zhang Y, Xu H, Casabianca LB. Interaction between cyanine dye IR-783 and polystyrene nanoparticles in solution. Magn Reson Chem. 2018 Nov;56(11):1054-1060. doi: 10.1002/mrc.4751. Epub 2018 May 31. PMID: 29771468. 15: Park JH, Lee BK, Park SH, Kim MG, Lee JW, Lee HY, Lee HB, Kim JH, Kim MS. Preparation of Biodegradable and Elastic Poly(ε-caprolactone-co-lactide) Copolymers and Evaluation as a Localized and Sustained Drug Delivery Carrier. Int J Mol Sci. 2017 Mar 21;18(3):671. doi: 10.3390/ijms18030671. PMID: 28335550; PMCID: PMC5372682. 16: Semenenko I, Portnoy E, Aboukaoud M, Guzy S, Shmuel M, Itzhak G, Eyal S. Evaluation of Near Infrared Dyes as Markers of P-Glycoprotein Activity in Tumors. Front Pharmacol. 2016 Nov 15;7:426. doi: 10.3389/fphar.2016.00426. 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