MedKoo Cat#: 408076 | Name: BB-Cl-Amidine
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Description:

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

BB-Cl-Amidine is a Novel Therapeutic for Canine and Feline Mammary Cancer via Activation of the Endoplasmic Reticulum Stress Pathway. BB-Cl-Amidine is a modified version of Cl-amidine that retains the functional components but possesses a C-terminal benzimidazole group designed to limit proteolysis of the C-terminal amide. BB-CLA reduced viability and tumorigenicity of canine and feline mammary cancer cell lines in vitro. BB-CLA activates the endoplasmic reticulum stress pathway in these cells by downregulating 78 kDa Glucose-regulated Protein (GRP78), a potential target in breast cancer for molecular therapy, and upregulating the downstream target gene DNA Damage Inducible Transcript 3 (DDIT3).

Chemical Structure

BB-Cl-Amidine
BB-Cl-Amidine
CAS#1802637-39-3

Theoretical Analysis

MedKoo Cat#: 408076

Name: BB-Cl-Amidine

CAS#: 1802637-39-3

Chemical Formula: C26H26ClN5O

Exact Mass: 459.1826

Molecular Weight: 459.98

Elemental Analysis: C, 67.89; H, 5.70; Cl, 7.71; N, 15.23; O, 3.48

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
100mg USD 1,450.00 2 Weeks
200mg USD 2,250.00 2 Weeks
500mg USD 3,250.00 2 Weeks
1g USD 4,250.00 2 Weeks
2g USD 7,450.00 2 Weeks
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Synonym
BB-Cl-Amidine; BB-CLA;
IUPAC/Chemical Name
N-[(1S)-1-(1H-benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-[1,1'-biphenyl]-4-carboxamide
InChi Key
YDOAWJHYHGBQFI-QHCPKHFHSA-N
InChi Code
InChI=1S/C26H26ClN5O/c27-17-24(28)29-16-6-11-23(25-30-21-9-4-5-10-22(21)31-25)32-26(33)20-14-12-19(13-15-20)18-7-2-1-3-8-18/h1-5,7-10,12-15,23H,6,11,16-17H2,(H2,28,29)(H,30,31)(H,32,33)/t23-/m0/s1
SMILES Code
O=C(C1=CC=C(C2=CC=CC=C2)C=C1)N[C@H](C3=NC4=CC=CC=C4N3)CCCNC(CCl)=N
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
Mammary cancer is highly prevalent in dogs and cats and results in a poor prognosis due to critically lacking viable treatment options. Recent human and mouse studies have suggested that inhibiting peptidyl arginine deiminase enzymes (PAD) may be a novel breast cancer therapy.
Product Data
Biological target:
BB-Cl-Amidine is a peptidylarginine deminase (PAD) inhibitor.
In vitro activity:
BB-CLA reduced viability and tumorigenicity of canine and feline mammary cancer cell lines in vitro. Additionally, BB-CLA activated the endoplasmic reticulum stress pathway in these cells by downregulating 78 kDa Glucose-regulated Protein (GRP78), a potential target in breast cancer for molecular therapy, and upregulating the downstream target gene DNA Damage Inducible Transcript 3 (DDIT3). Reference: BMC Cancer. 2018 Apr 12;18(1):412. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5898062
In vivo activity:
Canine and feline mammary cancer xenograft models were created using NOD scid gamma (NSG) mice, and were treated with BB-CLA for two weeks. There was an increase in the percentage of apoptotic cells in the BB-CLA-treated canine xenograft tumors compared to the controls (Fig. 6e), as well as a slight increase in apoptotic cells in the BB-CLA-treated feline xenograft tumors, however, this did not reach significance (Fig. 6e). Reference: BMC Cancer. 2018 Apr 12;18(1):412. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5898062
Solvent mg/mL mM
Solubility
DMSO 76.3 165.94
DMF 20.0 43.48
Water 70.0 152.18
Ethanol 54.5 118.48
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.09
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 459.98 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:
1. Ledet MM, Anderson R, Harman R, Muth A, Thompson PR, Coonrod SA, Van de Walle GR. BB-Cl-Amidine as a novel therapeutic for canine and feline mammary cancer via activation of the endoplasmic reticulum stress pathway. BMC Cancer. 2018 Apr 12;18(1):412. doi: 10.1186/s12885-018-4323-8. PMID: 29649984; PMCID: PMC5898062.
In vitro protocol:
1. Ledet MM, Anderson R, Harman R, Muth A, Thompson PR, Coonrod SA, Van de Walle GR. BB-Cl-Amidine as a novel therapeutic for canine and feline mammary cancer via activation of the endoplasmic reticulum stress pathway. BMC Cancer. 2018 Apr 12;18(1):412. doi: 10.1186/s12885-018-4323-8. PMID: 29649984; PMCID: PMC5898062.
In vivo protocol:
1. Ledet MM, Anderson R, Harman R, Muth A, Thompson PR, Coonrod SA, Van de Walle GR. BB-Cl-Amidine as a novel therapeutic for canine and feline mammary cancer via activation of the endoplasmic reticulum stress pathway. BMC Cancer. 2018 Apr 12;18(1):412. doi: 10.1186/s12885-018-4323-8. PMID: 29649984; PMCID: PMC5898062.
1: Sun YN, Ma YN, Jia XQ, Yao Q, Chen JP, Li H. Inducement of ER Stress by PAD Inhibitor BB-Cl-Amidine to Effectively Kill AML Cells. Curr Med Sci. 2022 Oct;42(5):958-965. doi: 10.1007/s11596-022-2637-x. Epub 2022 Oct 17. PMID: 36245030. 2: Ledet MM, Anderson R, Harman R, Muth A, Thompson PR, Coonrod SA, Van de Walle GR. BB-Cl-Amidine as a novel therapeutic for canine and feline mammary cancer via activation of the endoplasmic reticulum stress pathway. BMC Cancer. 2018 Apr 12;18(1):412. doi: 10.1186/s12885-018-4323-8. PMID: 29649984; PMCID: PMC5898062. 3: Stachowicz A, Sadiq A, Walker B, Sundararaman N, Fert-Bober J. Treatment of human cardiac fibroblasts with the protein arginine deiminase inhibitor BB-Cl- amidine activates the Nrf2/HO-1 signaling pathway. Biomed Pharmacother. 2023 Nov;167:115443. doi: 10.1016/j.biopha.2023.115443. Epub 2023 Sep 11. PMID: 37703660.