The indole ring system is present in many natural products, pharmaceuticals, agrochemicals, and other compounds of importance.1–8 The indole unit forms the basis for general BIM and TIM structures (Figure 1). The main purpose of this review is to provide a comprehensive summary of the various synthetic strategies to synthesize BIMs and TIMs. A number of BIM and TIM applications will be briefly pointed out, although this is not the main aim of this review. Many of the most important BIMs and TIMs were widely isolated from various terrestrial and marine natural sources. These natural products have novel structures and exhibit a range of important biological activities.9–19 Cancer chemotherapy with bis(3-indolyl)methane was recently reviewed and numerous activities are reported.20 3,3′-Diindolylmethane and derivatives also are used as dietary supplements for humans.21–24 BIMs inhibit bladder cancer growth,25 inhibit renal cell carcinoma growth,26 have growth inhibitory activity on lung cancer cells,27 are active against colon cancer,28,29 inhibit mammary tumor growth,30,31 induce apoptosis in prostate cancer,32–34 inhibit the proliferation process in breast tumor cells,35–50 have growth inhibitory activity on prostate cancer cell lines,51,52 have antitumorigenic activity,53 serve as topoisomerase IIR catalytic inhibitors,54 serve as inhibitors of the platelet-derived growth factor receptor kinase,55 exhibit antimicrobial and antifungal activities,56,57 exhibit antibiotic activity58 and antibacterial activity,59 have inhibitory effects on phenobarbital-induced hepatic CYP mRNA expression,60 serve as cytodifferentiating agents,61 are antiangiogenic and cytotoxic agents,62 have antimetastatic activity,63 have radical scavenging activity,64 growth promoting activity,65 and analgesic and anti-inflammatory activities,66 and are also utilized as tranquilizers67 and glass-forming high-tripletenergy materials.68 The oxidized form of BIMs and TIMs are utilized as dyes,69–74 as well as colorimetric sensors.75–78 A patent79,80 disclosed the synthetic method of chromogenic 3,3′-bisindolyl-4-azaphthalides 1 and their uses as color formers in pressureand heat-sensitive recording materials (Figure 2).81 A recent patent describes the synthesis of BIMs forming complexes 2 with radioactive metal ions (Gd3+), which are useful contrast agents for radio-imaging and visualization of various tissues and organs (Figure 2).82 Recently Maciejewska et al.83 used DNA-based electrochemical biosensors to demonstrate that bis(5-methoxyindol3-yl) methane, 3,84 considerably reduces the growth of cancer cell lines such as HOP-92 (lung), A498 (renal), and MDAMB-231/1TCC (breast) (Figure 3). Their results also indicate that BIMs could potentially be applied as chemotherapeutic agents against tumors.83,85 Recently Lee and co-workers have found that 1,1,3-tri(3indolyl)cyclohexane, 4, inhibits cancer cell growth in lung cancer cells of xenograft models (Figure 4).86 Ghaedi et al.87,88 have used BIMs coated on an aluminasodium dodecyl sulfate (SDS) surface for preconcentration and determination of Cu(II), Zn(II), Pb(II), and Fe(III) ions by flame atomic absorption spectrometry. Also BIMs and TIMs have been used as ligands for the synthesis of more complex molecules, and different properties of these complexed molecules have been investigated.89–94 † This paper is dedicated to Prof. Dr. Junes Ipaktschi on occasion of his 70th birthday. * To whom correspondence should be addressed. Fax: +98 21 88041344. E-mail: mshiri@alzahra.ac.ir. ‡ Alzahra University. § Bu-Ali Sina University. ⊥ University of KwaZulu-Natal. Figure 1. The structure of BIMs and TIMs. Chem. Rev. 2010, 110, 2250–2293 2250

Bis- and Trisindolylmethanes (BIMs and TIMs)†

Colorimetric metal ion sensors

Calixarenes, as nano-baskets, are considered an important group of macrocycles as the third famous host molecules after cyclodextrins and crown ethers have been subject to extensive researches in construction of many extractants, transporters, stationary phases, electrode ionophores and optical and electrochemical sensors over the past four decades. Because of the recent rapid growth in the publications of calixarene applications, this review paper has focused on different analytical applications of calixarenes in the main fields of separation, electroanalysis, spectroscopy and chemometrics. The objectives and the results of about 300 references mainly were published in recent 6 years with emphasis on the analytical applications were reviewed.

Analytical applications of calixarenes from 2005 up-to-date

A pyrimidine-naphthalene anchored Schiff base (receptor 1) showed Al(3+) selective conformational arrest by inhibition of its C=N isomerization (cis-trans) leading to its fluorescent switching in aqueous medium. Nevertheless the H(2)PO(4)(-)/HSO(4)(-) bailed receptor 1 from the Al(3+) arrest leading to its switching 'off'. This conformational arrest and bail of receptor 1 were highly specific as no other ion pairs were able to do the same. The detection limit of the receptor 1 towards Al(3+) is 1.49 × 10(-9) M and is the second highest for the same reported to date in the literature, while the same for H(2)PO(4)(-) and HSO(4)(-) were found to be 2.27 × 10(-7) and 2.91 × 10(-6), respectively. The mechanistic details of 'on-off' switching of the receptor 1 by the analytes have been explored through various spectroscopic studies along with theoretical calculations at density functional theory (DFT) level. The 'on-off' switching of receptor 1 through inputs Al(3+) and H(2)PO(4)(-)/HSO(4)(-) led it to mimic with INH logic function.

An Al3+ and H2PO4(-)/HSO4(-) selective conformational arrest and bail to a pyrimidine-naphthalene anchored molecular switch.

Chromofluorescent indicator for intracellular Zn2+/Hg 2+ dynamic exchange

Dual colorimetric sensoring bis(indolyl)calix[4]crown-6

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Dual colorimetric sensoring bis(indolyl)calix[4]crown-6