31362-50-2

Basic information

• Product Name: Bombesin
• Synonyms: 2-l-glutamine-6-l-asparagine-alytesi;bombesin acetate;Bombesin, Free Base;BOMBESIN SYNTHETIC >97% STIMULATES GASTR IN RE;Bombesin hydrate acetate salt;M.W. 1619.85 C71H110N24O18S;5-Oxo-L-Pro-L-Gln-L-Arg-L-Leu-Gly-L-Asn-L-Gln-L-Trp-L-Ala-L-Val-Gly-L-His-L-Leu-L-Met-NH2;Bombesin acetate salt hydrate
• CAS NO: 31362-50-2
• Molecular Formula: C₇₁H₁₁₀N₂₄O₁₈S
• Molecular Weight: 1619.85
• Product Categories: Peptide;Neuromedins and related
• Mol File: 31362-50-2.mol
• Article Data: 1

Chemical Properties

• Appearance: While lyophilized powder.
• Density: 1.5g/cm³
• Refractive Index: 1.681
• Storage Temp.: −20°C
• Solubility: 0.05 M acetic acid: 20 mg/mL, clear, colorless
• PKA: 13.04±0.46(Predicted)
• Merck: 13,1320
• BRN: 9611365
• CAS DataBase Reference: Bombesin(CAS DataBase Reference)
• NIST Chemistry Reference: Bombesin(31362-50-2)
• EPA Substance Registry System: Bombesin(31362-50-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: BD3480000
• F: 10
• Hazardous Substances Data: 31362-50-2(Hazardous Substances Data)

Usage

Uses

Gut tetradecapeptide with the ability to stimulate release of various hormones

Purification Methods

Purify Bombesin by gel filtration on a small column of Sephadex G-10 and elute with 0.01 M AcOH. This procedure removes lower molecular weight contaminants which are retarded on the column. The procedure should be repeated twice, and the material should now be homogeneous on electrophoresis, and on chromatography it gives a single active spot which is negative to ninhydrin but positive to Cl2 and iodoplatinate reagents. RF on paper chromatography (n-BuOH/pyridine/AcOH/H2O :: 37.5: 25:7.5:30) is 0.55 for Bombesin and 0.65 for Alytin. [Bernardi et al. Experientia Part 1 27 166 1971, Anastasi et al. Part 2 27 873 1971.] The hydrochloride has m 185o(dec) (from EtOH) [] D -20.6o [c 0.65, Me2NCHO/(Me2N)3PO (8:2)]. [For the stimulation of inositol phosphate see Lloyd et al. Biochem J 260 813 1989.]

InChI:InChI=1/C71H110N24O18S/c1-34(2)24-47(92-62(105)43(14-11-22-79-71(76)77)89-64(107)45(15-18-52(72)96)90-63(106)44-17-20-55(99)85-44)61(104)81-31-56(100)87-51(28-54(74)98)69(112)91-46(16-19-53(73)97)65(108)94-49(26-38-29-80-41-13-10-9-12-40(38)41)66(109)84-37(7)60(103)95-58(36(5)6)70(113)82-32-57(101)86-50(27-39-30-78-33-83-39)68(111)93-48(25-35(3)4)67(110)88-42(59(75)102)21-23-114-8/h9-10,12-13,29-30,33-37,42-51,58,80H,11,14-28,31-32H2,1-8H3,(H2,72,96)(H2,73,97)(H2,74,98)(H2,75,102)(H,78,83)(H,81,104)(H,82,113)(H,84,109)(H,85,99)(H,86,101)(H,87,100)(H,88,110)(H,89,107)(H,90,106)(H,91,112)(H,92,105)(H,93,111)(H,94,108)(H,95,103)(H4,76,77,79)/t37-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,58-/m0/s1

Synthetic route

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine (109425-56-1, 106982-77-8) + Fmoc-His(pg)-OH + Fmoc-Trp(pg)-OH + Fmoc-Gln(pg)-OH + Fmoc-Asn(pg)-OH + Fmoc-Arg(pg)-OH → Bombesin (31362-50-2)

Conditions

Yield

Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.583333h; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine; Fmoc-His(pg)-OH; Fmoc-Trp(pg)-OH; Fmoc-Gln(pg)-OH; Fmoc-Asn(pg)-OH; Fmoc-Arg(pg)-OH Further stages;

22%

...Expand

Upstream product

• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 68858-20-8 Fmoc-Val-OH 
• 35661-60-0 Fmoc-Leu-OH 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 71989-28-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine 
• 109425-56-1 N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine 

Relevant articles and documents

Design, synthesis, in vitro, and initial in vivo evaluation of heterobivalent peptidic ligands targeting both NPY(Y1)-and GRP-receptors— an improvement for breast cancer imaging?

Heterobivalent peptidic ligands (HBPLs), designed to address two different receptors independently, are highly promising tumor imaging agents. For example, breast cancer has been shown to concomitantly and complementarily overexpress the neuropeptide Y receptor subtype 1 (NPY(Y1)R) as well as the gastrin-releasing peptide receptor (GRPR). Thus, radiolabeled HBPLs being able to bind these two receptors should exhibit an improved tumor targeting efficiency compared to monospecific ligands. We developed here such bispecific HBPLs and radiolabeled them with68 Ga, achieving high radiochemical yields, purities, and molar activities. We evaluated the HBPLs and their monospecific reference peptides in vitro regarding stability and uptake into different breast cancer cell lines and found that the68 Ga-HBPLs were efficiently taken up via the GRPR. We also performed in vivo PET/CT imaging and ex vivo biodistribution studies in T-47D tumor-bearing mice for the most promising68 Ga-HBPL and compared the results to those obtained for its scrambled analogs. The tumors could easily be visualized by the newly developed68 Ga-HBPL and considerably higher tumor uptakes and tumor-to-background ratios were obtained compared to the scrambled analogs in and ex vivo. These results demonstrate the general feasibility of the approach to use bispecific radioligands for in vivo imaging of breast cancer.